planning my trip to chicago

The Perfect 3 to 4 Days in Chicago Itinerary

Published on April 10, 2024

by Olivia Ellis

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Chicago, standing as the third-largest city in the United States and the unofficial capital of the Midwest, is a blend of refinement, American industriousness, diversity, and a sincere, laid-back Midwest vibe. Whether you’re planning a 3 or 4 days in Chicago itinerary, this guide will offer you everything that creates the Windy City’s unique identity, from its classic foods, to the historic architecture lining the city.

Table of Contents

How Many Days in Chicago?

Chicago is a vast city and spending at least 3 days in the city is best to fully appreciate its diverse neighborhoods, iconic landmarks, and cultural institutions such as the Magnificent Mile, Millennium Park, and Lou Malnati’s Pizzeria.

Beyond this, 4 days or more in Chicago provide opportunities to dive deeper into Chicago’s neighborhoods such as Lincoln Park and Wrigleyville, or to explore at a more leisurely pace. Despite its size, Chicago is best enjoyed slowly, allowing you to get to know the city on a more intimate level.

Another component to factor in when deciding how long to spend in Chicago is the time of year. While winter in Chicago is famous for its blustery, snowy, and cold weather, the spring and summer open the city to an exciting atmosphere, with riverside events, beer gardens, and an abundance of outdoor activities such as city kayaking, or even swimming in Lake Michigan.

Because of this, I’d recommend spending more time in Chicago in the warmer weather vs a shorter trip in the winter unless you don’t mind spending time at your accommodation or your budget allows for time spent in a larger number of restaurants, or indoor sites/attractions.

Getting To & Around Chicago

Chicago serves as a major transportation hub in the United States, offering convenient access for both domestic and international travel. Chicago O’Hare, as the primary airport for the city and the state of Illinois, is often the most common arrival airport.

Alternatively, if you’re visiting from destinations within the Americas (from East Coast cities like Boston or Philadelphia or western cities like Los Angeles or Phoenix ) or are flying with specific international carriers, you may also land at Chicago’s Midway Airport.

Both airports provide CTA Train services into downtown Chicago, making your journey into the city speedy and affordable compared to pricey taxi or ride-sharing services. From O’Hare, the journey takes approximately 45 minutes depending on your final destination.

If you need to reach downtown from Midway Airport, expect a shorter 25-minute train ride.

In addition to its airport accessibility, Chicago also boasts convenient train connections, particularly for travellers exploring the Midwest.

For those seeking to economize or are interested in exploring other Midwest cities like Indianapolis, Detroit, Cincinnati, or Milwaukee, Amtrak offers a comfortable Midwest route connecting these cities at a lower cost than air travel.

On a grid system layout, Chicago is renowned for its efficient public transportation and easy navigability, offering convenience and accessibility. Many central sites and downtown areas are conveniently within walking distance, making exploration of the city simple and convenient.

During the chilly winter weather, or if you just prefer to use public transportation, Chicago’s public transportation is excellent, providing a convenient means of moving around the city.

The Chicago Transit Authority (CTA) offers an extensive network of buses and trains, and even water taxis in the warmer months, allowing convenient access to Chicago’s diverse neighborhoods and sites.

3 to 4-Day Chicago Itinerary

Whether you’re keen to eat your way through Chicago, explore the city’s rich sports culture, admire its unique blend of architecture, or spend time wandering through its many cultural icons, there is a lot to do on a trip to Chicago.

Day 1 – Magnificent Mile, Willis Tower & More!

Magnificent mile.

Day 1 begins in the center of the city in the Magnificent Mile neighborhood of Chicago.

The Magnificent Mile is a prestigious and bustling neighborhood located along Michigan Avenue in central downtown Chicago. Stretching approximately 13 blocks from the Chicago River to Oak Street, the neighborhood is renowned for its upscale shopping, landmarks, and atmosphere. If you want to explore this area with a guide, you can book a walking tour.

I find this area to be a wonderful spot to explore in Chicago first, as it defines the energy of the city while also offering great breakfast spots and well-known Chicago spots such as Willis Tower.

Skydeck at Willis Tower

One of the iconic buildings worth visiting while in the Magnificent Mile is the Willis Tower. Built in 1970 and originally known (and still referred to by locals) as the Sears Tower, the Skydeck at Willis Tower offers possibly the best views of the entire city.

The most renowned feature of the Skydeck is the Ledge, located on the 103rd floor, allowing you to experience the sensation of being suspended over Chicago’s landscape while enjoying incredible views of the Midwest capital city.

On the ground floor, you can enjoy an interactive experience that educates you in Chicago’s culture and history, all while in a fun environment.

Tickets and time slots for the Skydeck must be booked in advance , and adult admission starts at $32.

If you’re interested in visiting multiple attractions/experiences in Chicago, the Chicago CityPass or the GoCity Pass is a great way to save money.

Starbucks Reserve Roastery

After experiencing Chicago at its highest point, head back to the city’s streets and make your way to the world’s largest Starbucks, here in Chicago.

Whether you’re a coffee drinker, prefer tea or you’re somewhere in the middle, the roastery is an attraction in itself, encompassing 5 floors of various interest, from coffee, bakeries and cocktail bars, to immersive roastery experiences and even a roof terrace.

Chicago Architecture River Cruise

The classic Chicago Architecture River Cruise is a quintessential experience for visitors to the city. Whether you’re an architecture enthusiast or simply enjoy learning about Chicago’s history while taking in its incredible scenery, this cruise offers the ideal opportunity.

As you wind along the Chicago River, you’ll have the chance to learn more about the city’s architectural landmarks while enjoying one of America’s most famous cityscapes.

Tours are available year-round, with multiple companies offering varying lengths of tours led by knowledgeable locals. These tours typically last between 60 and 90 minutes and provide amenities such as comfortable seating, bathrooms, and heating in the winter.

Some even offer a full-service bar onboard. Tickets can be purchased online and are typically priced around $40 for adults, though prices may vary depending on the provider and time of year or day.

Day 2 – Millennium Park, Art Institute & Deep Dish Pizza

Millennium park & cloud gate.

Start your second day in Chicago by visiting one of the city’s most iconic landmarks: Millennium Park and its famous attraction, Cloud Gate, unofficially known as “the bean.”

Situated in the heart of the city within Grant Park’s northwestern section, Millennium Park spans 25 acres and was established in 2004 to commemorate the third millennium.

Today, it stands as a symbol of Chicago, boasting an impressive collection of public art, panoramic views of Lake Michigan’s shoreline, and the Cloud Gate sculpture by Anish Kapoor.

Spend time wandering around one of Chicago’s most beloved green areas, taking in the park’s fountains, art, structures, the Chicago Cultural Center and even possibly enjoying a skating session in the wintertime.

Nearby, you could also pop by to see the iconic Chicago theatre to glimpse another of the city’s most famous landmarks.

Art Institute

By this point on your trip, you’ve likely noticed that Chicago is a city synonymous with art. One of the best ways to delve deeper into this aspect of the city’s culture is by visiting The Art Institute of Chicago.

As one of the oldest and largest art museums in the United States, the Art Institute houses nearly 300,000 pieces of art, including works by Pablo Picasso, Edward Hopper, Claude Monet, and a diverse array of sculptures, prints, and drawings from around the world.

During your visit, you can learn more about the museum and its installations through free guided tours offered daily at 1:00 PM and 3:00 PM.

The admission cost for adults is $32, with discounted tickets available for children and seniors. They can be purchased online or you can also organise a guided tour.

Additionally, admission to The Art Institute is included in the CityPass for those participating in the program.

Chicago Pizza at Lou Malnati’s

The first food that probably comes to mind when thinking about Chicago is Chicago deep dish pizza, and there’s no better place to eat it than at Lou Malnati’s Pizzeria , a Chicago institution founded by the oldest family name in Chicago Pizza.

Taking pride in the pizzeria’s use of fresh ingredients and vine-ripened tomatoes, anything on the menu will likely be delicious, but I suggest ordering the “Malnati Chicago Classic” with sausage, cheese, and tomato sauce or the “Lou”, a vegetarian option with spinach, mushrooms, tomato, and a tasty cheese blend.

With over 50 locations in the Chicago metropolitan area, you’ll be hard-pressed to not find a location nearby. Regardless of where you go, there’s no doubt that digging into a gooey, cheesy deep dish pizza is one of the best things to do in Chicago and if you’re really a pizza lover then you can also join a pizza tour!

Day 3 – Riverwalk, Museums & London House Rooftop

Chicago riverwalk.

On your third day in Chicago, explore the city riverside by strolling along the Chicago Riverwalk, a scenic pedestrian path that stretches for 1.25 miles along the Chicago River.

The Riverwalk comprises four distinct districts: The Confluence, The Arcade, The Civic, and The Esplanade.

Along this picturesque route, you’ll discover lush greenery, restaurants, cafés, art installations, and seasonal performances.

The Chicago Riverwalk provides an ideal setting to unwind, relax, and soak in the city’s ambiance, making it a favorite spot for both locals and visitors and a true example of how to take advantage of city space. You can also learn more about its darker past on this walking tour.

Navy Pier or Field Museum of Natural History

Chicago offers a diverse array of museums and attractions, ensuring there’s something for everyone in the City of Big Shoulders.

For those seeking an immersive experience, Navy Pier is a must-visit attraction. Originally built in 1916 as a dock for freight and passenger ships, Navy Pier has transformed into an exciting spot with restaurants, bars, shopping, and entertainment options for all ages. Admission is free, and the pier is open year-round.

Alternatively, for a more traditional museum experience, consider visiting the Field Museum of Natural History. As one of the world’s largest natural history museums, it houses a large collection of artifacts and exhibits exploring biodiversity and human cultures.

From dinosaur skeletons to ancient artifacts, the Field Museum offers an interesting journey through natural history and anthropology. Tickets can be purchased online.

Drinks at London House Rooftop

Conclude your third day in Chicago at the renowned London House Rooftop bar. Perched atop the historic London House Hotel, this rooftop venue offers unparalleled nighttime views of the city’s iconic skyline.

Enjoy an elegant atmosphere and house cocktails as you take in the breathtaking vistas of the Chicago skyline. During the winter, cozy igloo capsules line the terrace, creating a festive atmosphere (reservations necessary).

Reservations are recommended in advance for popular times, and a smart casual dress code is in place.

Day 4 – Lincoln Park or Wrigleyville

Lincoln park.

If you’re spending 4 days in Chicago, consider exploring a neighborhood outside the downtown area.

Lincoln Park, located on the north side of the city, offers a leafy escape from the hustle and bustle of Downtown Chicago. Explore its residential streets lined with boutique shops and abundant food options.

Visit the neighborhood’s namesake, Lincoln Park, and learn more about various plant and flower species at the Lincoln Park Conservatory. Don’t forget to enjoy a lovely coffee or lunch at Floriole Cafe & Bakery.

Wrigleyville

For sports fans, spending a day in Wrigleyville is an exciting option for your last day in Chicago. This former working-class neighborhood, home to the Chicago Cubs, buzzes with activity, especially during baseball season.

During baseball season, the area offers an exciting atmosphere, boasting a wide array of sports bars and pubs.

Year-round, Wrigleyville offers a laid-back and friendly atmosphere with fun restaurants, seasonal outdoor concerts, film screenings, and even a farmers market.

And if you’re visiting during baseball season, be sure to buy tickets to a game to truly feel the soul of Chicago.

Where to Stay in Chicago

Moxy Chicago Downtown – Located in downtown Chicago, this hip, pet-friendly hotel is an excellent place to rest your head. It boasts 2 restaurants, air-conditioned rooms and an on-site fitness center.

The Hoxto n – This upscale, central hotel in the West Loop district is another great option in the windy city. There are on-site restaurants and beautiful rooms along with a great rooftop swimming pool – perfect for the warmer months!

Chicago Getaway Hostel – This cool hostel is a great budget option in the city. Offering lots of dorms and private rooms, there is a good social atmosphere. inviting common areas and a central location.

Not quite what you’re looking for? Click here to browse more Chicago hotels!

The Midwest is an entirely understated region of the United States, and a visit to its capital, Chicago, is the perfect way to find your way into the heart of its rich culture, warm hospitality, and urban landscape.

Are you planning to visit Chicago? Have any questions about this itinerary? Let us know in the comments!

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About Olivia Ellis

Olivia is a writer for The World Was Here First. Originally from Michigan, USA, she is currently living in Athens, Greece exploring Europe and filmmaking. When she’s not travelling or writing, Olivia can be found cooking delicious new recipes from around the world, reading, and spending time outdoors.

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3 Days in Chicago: Best Itinerary For A Trip To Chicago

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Looking to plan the best trip to Chicago, Illinois? Don’t stress – we have it covered! After visiting the Windy City on numerous occasions, we have created the Ultimate 3 Days in Chicago Itinerary. Including the best sights, must-do activities and local eats, our Chicago trip planner is all you need for a fantastic visit to Chi-town!

How To Plan A Trip to Chicago, Illinois

Planning a Chicago trip can feel overwhelming, but we are here to help! Chicago is steeped in riveting history, decorated with dazzling architecture and is famous for its food scene. While Chicago is bordered on the east by Lake Michigan, the city sprawls in all other directions.

Many of the top Chicago attractions are found in the very walkable downtown loop, and a few must-see Chicago sights are scattered further afield. We are sharing our top tips in a day-by-day Chicago 3-Day Itinerary so that you can plan a Chicago trip without worry.

Pro Tip:  Get (and stay) organized for your vacation to Chicago using our Trip Planning Printables !

3 Days in Chicago

Chicago is one of the best weekend destinations in the United States ! Visiting Chicago in 3 days is just enough time to see the highlights and get a taste of the city – and we squeeze just about all that we can into our perfect Chicago 3 Day Itinerary.

In fact, our trip plan is designed for a long weekend in Chicago – based on the assumption that visitors will arrive on Friday or Saturday and stay until Sunday or Monday. That said, our Chicago in 3 Days Itinerary can be used for trips on any days of the week (with just a few minor adjustments).

While we think three days in Chicago is a perfect amount of time for a visit, we know not all travelers are planning a 3-day Chicago trip. Therefore, we offer alternate Chicago itineraries – for shorter and longer trips – at the end of this article. Whether you are planning a 2-Day Chicago Itinerary, making plans for 4 days in Chicago or devising a Chicago 5-Day Itinerary trip plan, you can use our suggestions for your vacation!

What To Eat & Drink during your Chicago 3 Day Itinerary

Eating is one of the top things to do in Chicago in 3 days. The city is home to numerous legendary eateries – far too many to fit into one fun weekend trip in Chicago. To help, we have narrowed it down to the best Chicago food options.

Throughout our Chicago Three Day Itinerary, we highlight the most famous Chicago restaurants. Our food recommendations include classic eateries, Chicago’s best hot dogs, and – of course – iconic Chicago deep-dish pizza. For drinks in the Windy City, we feature locally brewed beer, swanky cocktail lounges and famous jazz bars. 

You will find all of our recommendations for food and drink sprinkled throughout our 3 Days in Chicago Itinerary.

Our Chicago Itinerary for 3 Days

Our 3-Day Itinerary for Chicago features the best of the city in an easy to follow day-by-day plan. At the end of the post, you will also find our tips for how to get there, where to stay and what to pack.

Our Chicago three-day itinerary includes everything you need to plan your ultimate trip to the Windy City. Save, Bookmark or Pin this post for your Chicago trip!

Day 1 of Your 3 Day Chicago Itinerary: City View, Park, Beach and West Loop

On the first day of your 3-day trip to Chicago, get settled into your accommodations (recommendations below) – then get an overview of the area. Next, explore the city’s best park and beach before setting off for a fun night in Chicago’s West Loop.

360 Chicago Observation Deck

Start your Weekend in Chicago Itinerary with the city’s best view! Zip to the top of 875 North Michigan Avenue – formerly the John Hancock Center  – to the 360 Observation Deck. The elevator ride only takes 40 seconds to travel 1,000 feet – so you should have no problem fitting the activity into your Chicago, Illinois trip plan!

Inside the 360 Observation Deck, visitors are greeted with incredible views of the Chicago skyline and Lake Michigan. Spend some time leisurely soaking in the view, sipping a drink at the bar or experiencing TILT – which claims to be the Highest Thrill Ride on the Planet. Buy your tickets now!

Historic Chicago Water Tower, Lincoln Park and North Avenue Beach

With your feet back on the ground, see some of the highlights of the City of Chicago. Walk to a historic landmark, through a beautiful park and along the shoreline on a Chicago beach.

The Chicago Water Tower still stands as a top Chicago landmark. Built in the 1860s, the tower is located on the famous Magnificent Mile. It is one of the few buildings that survived the 1871 Great Fire of Chicago. Although now in the shadow of skyscrapers, the tower is an important part of history and should not be missed by visitors to Chicago. 

Next up on your 3 Day Chicago Trip is the city’s best green space: Lincoln Park. Explore the myriad of paths that crisscross through the expansive lakeside Lincoln Park. If you are planning a trip to Chicago with kids, consider stopping at the Lincoln Zoo (it’s free!)! If the weather is cooperating, continue your walk on the sand at North Avenue Beach – and if it’s summertime, consider taking a swim in Lake Michigan!

Deep Dish Pizza for Lunch

For lunch, indulge in Chicago’s culinary creation: Deep Dish Pizza. Lou Malnati’s Pizzeria is a Windy City favorite known for their butter crust – and is a must-try during your 3 days in Chicago. The family-owned restaurant has several locations (including one just south of Lincoln Park).

That said, it’s not the only place to get gooey deep dish deliciousness on your weekend Chicago trip. There are dozens of highly acclaimed pizzerias serving up deep dish pies in Chicago. Giordano’s, Pizzeria Uno and Gino’s East are all good options for Chicago deep dish pizza. The Chicago Pizza and Oven Grinder Company, however, gets our vote and many rave reviews for their deep dish pizza and creative Pizza Pot Pies. 

Goose Island Fulton Street Brewery Tour

After lunch, continue to the next stop on your Three Days in Chicago Itinerary: The Chicago-born Goose Island Brewery. Established as a small city brewpub in 1988, Goose Island is now a globally recognized beer brand (thanks in no small part to it’s acquisition by Anheuser-Busch in 2011).

At the Fulton Street Brewery and Taproom, patrons are invited to take a brewery tour to witness the behind-the-scenes production process…and then sip delicious, fresh beer. Even if you skip the tour, this is a fun brewpub and should definitely be included on a beer-lovers three day Chicago Itinerary!

Time Out Market Chicago

We were first introduced to the concept of Time Out Markets in Lisbon, Portugal , where we were absolutely thrilled that they brought the best local chefs under one roof. At the Chicago Time Out Market, which is situated in the heart of the West Loop dining district, the idea is the same – and we think it’s a must for your Chicago Itinerary!

Visitors can order dishes from any of the carefully selected 18 Chicago chefs. The warehouse-style market encompasses 50,000 square feet of dining space – and includes 3 bars and a rooftop terrace.

The buzzing Time Out Market features Chicago classics, international fare and decadent desserts that are all well-recognized brands of the city.

A Night Out during Your 3 Day Itinerary Chicago

While patrons can linger at the Time Out Market bars, with only a weekend in Chicago, we recommend moving on to one of the hip bars in the West Loop (or beyond).

Best Bars for Day 1 of your 3 Days in Chicago

There is no shortage of hangouts in West Loop, so where you go depends on your taste. To help you decide, we’ve rounded up a short list of some of the fun bars you can add to Day 1 of your Chicago 3 Day Itinerary.

Blind Barber

Just a block west of the Time Out Market is Blind Barber, a barbershop by day…and a swank, 70s-style speakeasy by night.

Emporium Fulton Market

The fun Emporium Fulton Market is just down the street to the east – and features an array of arcade games and craft cocktails.

Lone Wolf Chicago

A favorite local neighborhood spot, the Lone Wolf is a classic and comfortable establishment to add to your Chicago night out.

Haymarket Brewery

If you are in search of Chicago craft beer, don’t miss Haymarket Pub and Brewery. They also feature live music on weekends.

Green Mill Cocktail Lounge

However, visitors who are planning a trip to Chicago and want to sip a cocktail inside a Chicago institution should leave the West Loop and head uptown to Green Mill Cocktail Lounge.

The iconic bar opened in 1907, was partly owned by Al Capone during Prohibition, has hosted famous singers – such as Billie Holiday – and now regularly features jazz and poetry nights. Just be prepared; it’s a bit north of the city, there is a cover charge, it’s cash only and seating is first come, first served.

Day 2 of Your Chicago Itinerary in 3 Days: The Loop, Architecture and Windy City Sports

On the second day of your Chicago in a Weekend Itinerary, explore top attractions on foot and by boat, then end the day in a classic northside neighborhood, maybe even watching a baseball game!

Breakfast At The Famous Lou Mitchell’s

For breakfast on Day 2 of your Chicago trip, indulge in a hearty Midwest-style meal at the iconic Lou Mitchell’s. For a 100 years, the diner has been serving up omelets and pouring coffee for hungry patrons. Definitely old school and a little quirky (they hand out Milk Duds), eating at Lou Mitchell’s is a Chicago must!

Union Station Chicago

Ease into your full day of Chicago sightseeing at the landmark Union Station. Opened in 1925, the station serves Amtrak and Metra commuter lines – and ranks as the busiest rail station in the United States outside of New York City . Occupying an entire city block, the classic Great Hall waiting room is at the center – and is recognizable from many popular Hollywood films including The Untouchables and My Best Friend’s Wedding.

The Loop Walking Tour

Spend the rest of the morning walking off your Midwest breakfast on a self-guided walking tour of the Chicago downtown Loop. The district features historic architecture, lush parks and intriguing artworks. Exploring this area is an absolute must when visiting Chicago.

Trip Planner Chicago Loop

Begin your discovery at the well-recognized Willis Tower (formerly the Sears Tower), which ranked as the tallest building in the world when it was completed in 1973. Visitors can soar to the 103rd floor Skydeck Chicago (be sure to buy your ticket in advance !). After visiting the Willis Tower, continue on your tour of the Chicago Loop.

Explore the following Chicago Loop sights (in order) and use this link to Google Maps for locations.

• Daley Plaza (and Picasso’s Untitled artwork)
• Miro’s Statue
• Chicago Theater (and famous Chicago sign)
• Old Marshall Field Building (and legendary clocks)
• Chicago Cultural Center (and Tiffany Dome)
• Millennium Park and Grant Park (Cloud Gate mirrored sculpture a.k.a. The Bean , Crown Fountain – then detour out of the park to see the historic Route 66 Begin sign and go one block west to see the famed Palmer House Hilton Hotel – Chicago Stock Exchange Arch, Buckingham Fountain)
• Queen’s Landing
• Lakeshore Trail  
• Chicago Riverwalk (view The Wrigley Building and Tribune Tower across the river)
• DuSable Bridge

Billy Goat Tavern For Lunch 

End the tour by crossing the DuSable bridge and walking north on Michigan Avenue to the Plaza of the Americas – then have lunch at Billy Goat Tavern. This iconic eatery is surely a highlight of any weekend trip to Chicago. 

Established in 1934, the Billy Goat Tavern opened at the Lower Michigan Avenue location in 1964 and has been serving their famous “Cheezborgers” ever since. The original owner was the historic instigator of the Chicago Cubs’ Curse of the Billy Goat and the tavern was the inspiration for the Olympia Café in 1970s Saturday Night Live sketches .

Chicago Architecture River Cruise

After lunch, hop on a boat for a different perspective of the Chicago skyline – it’s an absolute must for a summer Chicago weekend itinerary. Enjoy an entertaining hour-long river cruise along the three branches of the Chicago River. The on-board tour guide shares the history of the city and more than 40 buildings that you will pass along the way. Book your seat now!

Wrigleyville (and a Cubs Game)

Home to the much-loved Chicago Cubs (unless you’re from the South Side or St. Louis), Wrigleyville is a north side neighborhood packed with lively bars and fantastic eateries. The historic Wrigley Field is at the heart of the neighborhood – and attending a baseball game (regardless of who you’re rooting for) is a highlight of any itinerary for Chicago.

If the Cubbies are not playing while you are vacationing in Chicago, it is still worth visiting the neighborhood for dinner and drinks. Visit one of the famous Clark Street sports bars – like the Cubby Bear or Sluggers – for simple grub and drinks (or go for a gastropub dinner at Mordecai).

If the Cubs are away and seeing a baseball game is at the top of your list of things to do in Chicago, then check the South Side White Sox schedule.

Outside of the summer baseball season, there are numerous pro sports events that you could add to your three days in Chicago trip plan. Check schedules for the world famous Chicago Bulls (basketball), Chicago Bears (football), Chicago Blackhawks (ice hockey) and Chicago Fire (soccer).

Day 3 of Your Weekend in Chicago Itinerary: Walking Trail, Hot Dogs & Navy Pier

Wrap up your 3 Days in Chicago Itinerary with more sightseeing, eating and walking it off! Start the day at a cool urban park, embark on a local food tour, get a birds’ eye view of the city and end your Chicago tour itinerary at tourist hotspot, Navy Pier.

Walk Off the Food You’ve Eaten in Chicago in 3 Days

When we plan a trip to Chicago that includes gorging on the local fare, we also carve out time to walk it off. While our Weekend in Chicago Itinerary naturally includes a lot of walking between sights, there are two fabulous places to hit really stretch your legs: 606 Bloomingdale Trail and Lakefront Trail.

The 606 Bloomingdale Trail 

Similar to the New York City Highline and the Paris La Promenade Plantee, the Bloomingdale Trail at The 606  is a repurposed elevated train track-turned-public-park. Running three miles through four districts (Wicker Park, Bucktown, Humbolt Park and Logan Square) on Chicago’s northwest side, the walking trail features art installations and hosts local events.

We recommend walking The 606 from east to west. Churchill Field Park is a great place to hop on the trail. Pop into Mindy’s Bakery, run by famed Chicago chef Mindy Segal, for an incredible breakfast before starting your walk. Just be warned, there will likely be a line out the door – breakfast at Mindy’s is one of the top things to do in Chicago on a weekend – and it’s closed Monday – Wednesday.

Lakefront Trail

As the name suggests, the Lakefront Trail fronts Lake Michigan – and, for many visitors, walking along the shoreline is a highlight of a 3 Day Itinerary for Chicago. The trail stretches for 18 miles and can be used by bicyclists and pedestrians. From the path, there are fabulous views of Chicago and the shoreline. Hop on at any point and walk as far as you would like!

Famed Chicago-Style Hot Dogs

Your Chicago Trip Planner is not complete without consuming at least one hot dog. Chicago Dogs are noted for being ‘dragged through the garden’ – meaning, piled high with toppings that include mustard, onions, relish, tomatoes and a dill pickle spear sprinkled with celery salt (but never ketchup!). Unarguably, the place to get a Chicago Dog is at Portillo’s – a long-time, well-known chain that originated in the city (and has now expanded across the United States). 

In addition to hot dogs, Portillo’s also serves fabulous Italian Beef Sandwiches – another must-eat in Chicago! However, if you are just going after the beef, then go to Al’s #1 Italian Beef – an iconic Chicago eatery chain that was established in 1938.

Alternatively, Join a Chicago Food and Drink Tour

While we have included some of the top must-eat restaurants in our Chicago in a Weekend Itinerary, there is still more feasting to do! Rather than choosing one place for lunch on the last day of your 3 perfect days in Chicago, taste-test your way through the city. Join an expert guide in the local foodie scene to discover favorite haunts and classic fare including Deep Dish Pizza, Italian Beef, famous Chicago Hot Dogs and more. Get the details here!

Explore Navy Pier Chicago

Complete your Weekend in Chicago Itinerary with an afternoon at Navy Pier. Like Pier 39 in San Francisco , Navy Pier caters mostly to tourists, but a fun and enjoyable time is had by all. Featuring a wide array of restaurants, souvenir shops and art exhibitions, Navy Pier is a must-see in Chicago…and a great way to end your Chicago 3-Day trip!

More Chicago Things To Do

We have outlined our best Chicago itinerary, including the top things to do when you visit Chicago in 3 days. Still, how to plan a trip to Chicago will depend on your specific interests. Therefore, we are sharing more fun things to do that you may want to add to your weekend trip to Chicago Itinerary.

Shopping on The Magnificent Mile

Visitors who want to go shopping in Chicago will find there is no shortage of stores! The best place to shop is on the famed Magnificent Mile, which is the section of Michigan Avenue that runs from the Chicago River north to Oak Street. The cosmopolitan street is lined with an astounding 460 retailers – from recognizable department stores to chic boutiques – and is a top destination for fashionistas planning a 3 Days in Chicago Itinerary.

Chicago Museums

With more than 65 museums in Chicago, there is certainly something for everyone. Whether it’s art, history or science that piques your interest, you can find a museum to include on your Chicago trip itinerary!

Chicago Trip Ideas: What Museums to Visit

When you plan trip to Chicago, it can be difficult to choose which museums to visit on your vacation. We are highlighting a few of the renowned museums to help you decide. 

Art Institute of Chicago: The city’s most famous art museum, the Art Institute is a top pick for 3 days in Chicago trips ( buy Skip-the-Line Tickets! ).

Museum of Science and Industry: The hands-on, family-friendly Museum of Science and Industry is a good museum to visit if you are planning trip to Chicago with kids. 

Museum of Contemporary Art: The fun and modern Museum of Contemporary Art is a fantastic museum to visit on a weekend getaway to Chicago. 

Shedd Aquarium: Whether you are planning a Chicago trip with family, as a couple or with a group of friends, the state-of-the-art Shedd Aquarium is a good addition to your Chicago vacation planner. 

The Field Museum: A fascinating museum of mummies and dinosaurs, the Field Museum is an excellent stop on a 3 day trip to Chicago. 

Adler Planetarium: If time permits in your itinerary, plan a day in Chicago that includes stargazing at the Adler Planetarium. 

Pro Tip : Save money and skip lines with a Chicago CityPass ! If you are planning on visiting more than one museum during your three days in Chicago, it will almost definitely save you money!

Go to a Theater Performance in Chicago

Need more ideas of what to see in Chicago in 3 days? Go to a show! Chicago has a vibrant theater district comprised of more than 250 theaters. From world-class productions to comedy acts, some of the best actors and comedians in the world have graced the stages in Chicago. 

Chicago Neighborhood Exploration

One of our favorite things to do in any city is explore the unique neighborhoods and districts. Throughout our Chicago weekend trip itinerary, we have featured some of the top Chicago districts – but we by no means covered them all. Some of the other places to explore in Chicago are Chinatown, Little Italy, Lincoln Park, Wicker Park, Boystown and Roscoe Village.

How Many Days in Chicago?

We think 3 days in Chicago is the perfect amount of time to get acquainted with the city…but we would have no problem entertaining ourselves for a week in Chicago – or longer!

How many days you spend in Chicago will ultimately depend on your interests, budget and availability.

Sample Chicago Itineraries 

We have outlined a perfect plan for a long weekend in Chicago – but what if your trip plans include more (or fewer) days? No worries! Using our 3-Day Chicago Weekend Itinerary as a base, we are sharing our best suggestions for longer and shorter trips.

1-Day Chicago Itinerary

Planning a Chicago in One Day Itinerary is not easy. The city has so many iconic sights and delicious things to eat that it is difficult to pick and choose which ones to include in your Chicago trip plan. However, if one day is all you have, then we suggest making the absolute most of it!

Chicago 1 Day Itinerary Trip Plan

For us, an ideal One Day in Chicago Itinerary would follow Day 2 in our above plan of what to do in Chicago in three days. However, unless you are passionate about baseball, rather than going to Wrigleyville we would recommend spending the evening on Navy Pier or in West Loop.

Chicago Itinerary 2 Days

With 48 hours in Chicago, visitors can plan a Chicago 2-Day Itinerary that is succinct and hits almost all of the highlights.

Chicago 2 Day Itinerary Trip Plan

If you are planning a 2-Day Itinerary for Chicago, we suggest following Days 2 and 3 of our outlined plan for what to see in Chicago in 3 days. Again, if the Cubs were not playing, we would skip Wrigleyville and spend the evening in West Loop, even squeezing in the Goose Island Brewery Tour if possible.

Chicago Itinerary 4 Days

Planning a 4-Day Chicago Itinerary allows for a lot more sightseeing – including many of the museums that we skipped in favor of neighborhood exploration. 

Chicago 4 Day Itinerary Trip Plan

To organize an ideal 4 Days in Chicago Itinerary, we would follow our Chicago 3-Day Itinerary – then, on the last day, we would use the CityPass to visit the top museums, including The Art Institute, Field Museum, Shedd Aquarium and Museum of Science and Industry.

Chicago Itinerary 5 Days

Spending 5 days in Chicago allows for a lot more adventures at a somewhat leisurely pace.

Chicago 5 Day Itinerary Trip Plan

To plan a perfect 5-Day Chicago Itinerary, we recommend following the above outlined Chicago 4-Day Itinerary – then, on the last day, spend the morning discovering a new neighborhood, go shopping on the Magnificent Mile in the afternoon and attend a theater performance in the evening – then get a drink at the Lobby Bar in the posh Palmer House for a nightcap.

Tips For Planning Your Trip to Chicago

Now that you know what to do in Chicago in 3 days, we have a few more essential tips for your trip!

Organize your Chicago Travel Plan

There is a lot more to Chicago trip planning than determining what to see and do. Don’t worry – we share our top tips for planning a vacation in Chicago – from how to get there to what to pack – in the next sections. 

As you research Chicago vacation ideas and start making reservations, make sure you stay organized. A useful travel planner – like our Printable Travel Planner – will help you keep track of all the details of your perfect Chicago travel itinerary! 

How To Plan Chicago Trip Budget

A trip to Chicago, Illinois can be expensive – but it doesn’t have to be. Travelers who are planning to spend a weekend in Chicago on a budget have many options for exciting entertainment. We suggest skipping sights with high-priced tickets and partaking in many of the cheap and free things to do in Chicago. 

Get our tips on how to plan the best budget trips – plus get our free Vacation Budget Planner – to help plan your budget Chicago, Illinois trip! 

How To Get to Chicago

An essential consideration for your Chicago trip itinerary is how to get there! Chicago can be reached by car, bus, train or plane. On our trips to Chicago, we have always arrived via plane.

Flying To Chicago

There are two major Chicago airports: O’Hare International (ORD) and Chicago Midway (MDW). Both airports have their pros and cons – O’Hare is an enormous airport serviced with flights from around the world ( London , Hong Kong , Tokyo , Munich , etc.), but is far from the city center. Alternatively, Midway dominated by Southwest Airlines and they service mostly US domestic destinations, but is much closer to downtown Chicago.

Both airports are connected to downtown Chicago via public transport (the Blue Line from ORD and the Orange Line from MDW), but visitors can also use taxis, Uber or private transport , too. 

Start your search for the best airfare and flight times on SkyScanner  – but first read our Top Tips for Finding Cheap Flights .

Trip To Chicago by Train

If you are traveling to Chicago from another city that is serviced by Amtrak, then you can also plan a Chicago 3 Days Itinerary with arrival by train. That said, the journey will likely take longer and could even be more expensive than flying – so bear that in mind as you make your trip plans! 

Getting Around Chicago

Downtown Chicago is very walkable – but getting to the districts outside the city center require transportation. Besides your own two feet, visitors have options when it comes to getting around Chicago – from the ‘L’ train to CTA buses to bikes to scooters to Uber and Lyft. 

Public Transportation

Chicago has one of the most extensive public transportation systems in America and makes getting around Chicago fairly easy. Both the ‘L’ train and buses have extensive networks. The affordable fares can be paid using a Ventra account – and both 1-Day and 3-Day flat fare tickets are available for your Chicago visit. Find Chicago Transit fare info here . 

More Ways to Get Around Chicago

That said, using Uber or Lyft is likely much more convenient – and if traveling in a group – not too expensive.

We do not recommend driving a car during your Chicago weekend itinerary; parking is a hassle and can cost a bundle.

Chicago Hop On Hop Off

The Chicago Big Bus provides an excellent service for travelers who want to easily get from one tourist site to the next. The Hop On Hop Off Chicago buses are double-decker, open-air vehicles that make stops at all top attractions – and include informative on-board commentary! Buy your ticket!

Where To Stay in Chicago

Although there are hundreds of places to stay in Chicago, for your Chicago vacation itinerary, we recommend choosing downtown accommodations.

Chicago Hotels

If you are going to splurge for 3 nights in Chicago, there is no better place than The Palmer House Hilton . The historic hotel, featuring a gorgeous lobby, is in a prime location within the Theater and Financial Districts near Millennium Park.

That said, there are hotels in Chicago that fit every budget and style. To find the perfect Chicago hotel for your stay, start your search on Booking.com – like we do. Use the filters to select the hotel amenities that are most important to you – and use the map to find the best location. Be sure to read all of our best tips for booking hotels !

3 Day Trip Chicago Vacation Rentals

In our travels, we often use Airbnb to find affordable apartments in the places we visit. In fact, we have found that Airbnb is sometimes less expensive – and offers more space – than most hotel rooms.

However, this is not always true on short stays. Be sure to check the extra fees when booking a short trip – like 3 days in Chicago – before confirming your Airbnb stay.

What To Pack For Your Chicago Trip

We have a few final tips and packing hacks for what to pack for your 3 perfect days in Chicago. Need a packing checklist? Grab your FREE Printable Packing Checklist here !

Weather Appropriate Clothing for Your Chicago 3 Day Itinerary

What you pack in your suitcase for a trip to Chicago will depend on the season. Winters can be frigidly cold, summers are often unbearably humid, springtime is wet and autumn is likely to be brisk, hot or soggy. So yes, the frequent weather changes make planning what to pack for your trip a bit of a conundrum.

If you are taking a Chicago summer vacation, pack loose-fitting clothes, a wide-brimmed travel hat and sunscreen . In the wintertime, you will need a winter coat, cozy cap  and gloves . And, if traveling in the spring or fall, make sure to bring a packable raincoat and travel umbrella . Because the weather can fluctuate, it is best to pack clothing that can be layered and carry a great day bag for quick wardrobe changes and all your everyday essentials .

Walking Shoes for Your Itinerary for Chicago

Our Chicago 3-Day Trip Itinerary includes a ton of walking! We recommend wearing a pair of comfortable walking shoes for trekking around the city. I like to wear these lightweight shoes by Columbia and Kris prefers wearing his Merrell trail shoes for city walks.

Travel Camera

Chicago is incredibly photogenic – and, if you are anything like us, you will be snapping a lot of pictures during your three days in Chicago. Instead of using your cell phone camera to capture the sights, we recommend upgrading to a real camera . We travel with a DSLR Canon Rebel and use an everyday 18-135mm lens . The camera comes bundled with tons of accessories – so it is perfect budget camera for beginners!

US Travel Insurance for Your Chicago Itinerary 3 Days

Travel insurance can be useful on all kinds of trips – even a long weekend in Chicago. It can cover unfortunate situations, like cancelled trips, lost luggage and more. Check rates and coverage on World Nomads .

Start planning your trip to Chicago, Illinois ! Search for the lowest airfares , the best accommodations and fun things to do …then start packing !   Want more travel planning tips? Head over to our Travel Planning page for more information and tips on traveling – and for country-specific information, take a look at our Travel Guides page !

Visit More Top Destinations In The USA

Planning other trips in the United States? Use our detailed guides to discover the best of cities across America (and some Underrated US Destinations ). In fact, we wrap up our top picks for the best places to go in our guide, 22 Weekend Getaways in the US !

Already have a destination in mind? We offer comprehensive guides for Phoenix , Columbus OH , Indy ,  Portland , Austin , Seattle , Boston , Denver and San Diego – to name a few! 

Up for a US road trip? Use the tips in our articles for the Oregon Coast , Columbia River Gorge , the California Coastline and through amazing Montana.

Find all of our tips for traveling in the United States on our USA Travel Destinations Page . 

We Want To Know: Do you have any advice on how to spend 3 days in Chicago? Is there anything you would add to our Chicago Itinerary? Give us your best tips on how to plan a Chicago trip in the comments below! 

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3 Days in Chicago: The BEST Weekend Itinerary (By a Local!)

Planning 3 days in Chicago and seeking the perfect itinerary? I have lived in Chicago almost my entire life so I have created the perfect detailed Chicago 3 day itinerary with the best things to do, best places to eat, where you should stay, and all of my top tips, so that you can spend less time planning and more time enjoying the Windy City.

There is so much to do in Chicago but three days is enough to see most of Chicago’s top attractions . I have grouped each day by neighborhood so you don’t have to waste time getting around.

3 Days in Chicago Itinerary

3 Days in Chicago – Day 1

Lets start Day 1 in Chicago by enjoying some of the best views Chicago has to offer.

360 CHICAGO

For panoramic views of Chicago, head to 360 CHICAGO (formerly John Hancock Observatory), a public observatory on the 94th Floor of 875 N Michigan that offers breathtaking 360 degrees views of the city skyline and Lake Michigan.

The 360 Chicago observation deck is also home of TILT – Chicago’s highest thrill ride – an enclosed moving platform that literally tilts you out over Michigan Avenue from the 94th Floor.

Tip: 360 Chicago tends to be less busy and has shorter lines that the taller Willis Tower (on Day 2) but it is still best to visit in the morning to avoid crowds. (Click here to buy a skip the line ticket ).

Shop (or Window Shop) on the Magnificent Mile

After visiting 360 Chicago, walk south on Michigan Avenue and join the throngs of visitors and locals shopping (or window shopping) on The Magnificent Mile. The Magnificent Mile (or The Mag Mile), is an upscale section of Michigan Avenue, running from Oak Street to the Chicago River. Although some of the stores on Michigan Avenue are pricey, it is totally free to window shop. Landmarks on the Mag Mile include the historic Chicago Water Tower, the Tribune Tower and the Wrigley Building skyscraper.

Take an Architecture River Cruise

Chicago has amazing architecture and the best way enjoy it is by taking an architecture river cruise . Because the water sometimes freezes, river cruises don’t usually run in the winter.

If you are visiting Chicago in the summer, you can do a longer combined architecture river and lake cruise to see the skyline from the lake as well.

An alternative to a river cruise is to take a walk along the Chicago Riverwalk . The Riverwalk is one of the best spots in Chicago for people watching and there are also restaurants , shops and places to sit along the way. You can see a map of attractions on the Riverwalk here .

Go on a Gangsters Tour

Chicago has a long  history of organized crime and is famous for being the home of mafia figure Al Capone. There are many mob tours for those that want to learn more about the history of organized crime.

Food or Drinks with a View

Chicago has several rooftop bars and restaurants with amazing views of Chicago.

Cindy’s (12 S Michigan Ave) is a restaurant and bar on the rooftop of the Chicago Athletic Association Hotel located across Millennium Park which offers panoramic instagram worthy views of Millennium Park and Lake Michigan. This is a popular spot and the wait for the elevator can be long but if you visit around the time it opens (10 am on the weekends and 11 am on some weekdays) you can enjoy the great views without the crowds.

LH ON 22 (85 East Wacker Drive) -Enjoy classic cocktails and small bites from the outdoor LH terrace of LondonHouse Chicago which offers great views of the Chicago River, Lake Michigan and the Magnificent Mile.

The J. Parker (1816 N Clark St) is a stylish bar and restaurant on the rooftop of the Hotel Lincoln with great views of Lincoln Park.

3 Days in Chicago – Day 2

From the highest vantage point of the city to the famous Bean, Day 2 in Chicago will take you to Chicago’s best and most famous attractions.

Skydeck at Willis Tower

The Skydeck at Willis Tower (formerly known as the Sears Tower and what locals still call it) is the most well known of Chicago’s two tall skyscrapers with public observatories. The Willis Tower is the tallest building in the Western Hemisphere and was the tallest building in the world from 1974 until 1998.

If you are not scared of heights, you can stand on the Ledge’s glass boxes that extend out over 4 feet from the Skydeck.

Tip:   Lines for the Skydeck can get very long (especially on weekends) so avoid the crowds it is best to visit first thing in the morning as soon as it opens or in the evening. (Click here to buy a skip the line ticket ).

See The Bean at Millennium Park

If you have seen photos of Chicago on social media, chances are you have seen photos of Cloud Gate (also called The Bean), the famous mirrored sculpture in Millennium Park.

Please note that due to construction, public access and views of Cloud Gate are limited through spring of 2024.

Although The Bean is very touristy, don’t skip it. It is one of the most instagrammable places in Chicago and it is a great spot to take photos to remember your trip to Chicago.  The Bean is usually crowded especially in the summer and on weekends so if you don’t want other people in your photos visit early in the morning.

The free Millennium Park is part of Grant Park and also includes the Jay Pritzker Pavilion, the Crown Fountain sculpture and Lurie Garden. In the winter, there is a free ice skating rink right in front of the park. On hot summer days, kids (and some adults) love to splash in the water from the Crown Fountain .

If you are visiting Chicago with toddlers and young kids, you might want to also visit Maggie Daley Park , a large public park connected to Millennium Park that has play areas for kids of various ages, a fieldhouse, climbing wall and another ice-skating ribbon in the winter.

Art Institute of Chicago

Chicago has many great museums which are worth visiting but my top pick is the  Art Institute of Chicago conveniently located next to Millennium Park. It is one of the oldest and largest art museums in the United States and is frequently found on lists of the top museums in the world. (Click here to buy a skip the line ticket if you want to avoid long lines).

Some locals consider Navy Pier a bit of a tourist trap, but it is a not to missed attraction especially for those visiting Chicago with kids. Navy Pier is full of fun things to do including a large Ferris wheel, rides and games, the Chicago Children’s Museum and several shops, restaurants (including Giordano’s and Garrett Popcorn Shops) and bars. Navy Pier is also the starting point for various sightseeing cruises and boat rides.

Tip: If you are visiting Chicago in the summer, stay or come back for the free fireworks at Navy Pier every Wednesday at 9 pm and Saturday night at 10 pm. You can even watch the show from the water on a sightseeing cruise .

3 Days in Chicago – Day 3

Here are my suggestions for your third and final day sightseeing in Chicago. If you are visiting Chicago on a Sunday morning, head to Maxwell Street Market , one of the best places for Mexican food.

Visit One or More Museums

Chicago has many great museums which are worth visiting. The Field Museum , the  Shedd Aquarium and Adler Planetarium are all located close to each other on The Museum Campus. The Adler Planetarium Skyline Walk has one of the best skyline views of Chicago .

The Museum of Science and Industry is located in Hyde Park and is a bit out of the way from downtown Chicago but it is a really fun museum with hands-on activities and interactive exhibits. If the weather allows and you have extra time in Hyde Park, you might want to check neighboring Jackson Park . This park has cherry blossom trees in the spring and it also has a free Japanese garden.  Promontory Point is about a half mile away and has great skyline views of Chicago.

Tip:   If you are visiting a few museums and indoor attractions, consider purchasing a Chicago CityPASS or Go Chicago Card to save money on entrance fees.

Explore the Lakefront Trail and Beaches

Chicago’s Lakefront Trail is a paved path on a 18-mile-long stretch along Lake Michigan and it is a great spot to people watch and get some exercise.  In the summer and weekends, the lakefront is packed with locals and visitors walking, running and riding bikes.  You can find a map with the access points here .

Most people don’t think of Chicago as a beach destination but Chicago has many beaches on Lake Michigan.   Oak Street Beach and Ohio Street Beach are conveniently located close to the major tourist attractions. North Avenue Beach is more of a party beach and is located close to Lincoln Park.

More Things to Do in Chicago

If you have more time or not a fan of museums or tall buildings, here are some more fun things to do in Chicago:

Find Street Art

Chicago is full of street art and there are always new murals popping up.  One of the most famous Chicago murals is “Moose Bubblegum Bubble” (pictured above) by Jacob Watts which located at 33 E. Ida B. Wells Drive (formerly 33 E. Congress Parkway). It is part of the Wabash Arts Corridor which is walking distance to Millennium Park, The Art Institute of Chicago and other well known tourist attractions. You can find more detailed mural walks in the Loop here .

Another famous mural is The Greetings From Chicago Mural at 2226 N Milwaukee Ave, in Chicago’s Logan Square neighborhood. You can see this mural and other street art on this street art tour .

Another neighborhood that has a high concentration of street art (as well as great Mexican food) is Pilsen.

Watch a Cubs Game at Wrigley Field (or attend another sporting event)

Chicago is known for their love of their sports teams, so if you are visiting during the season you might want to attend a sporting event. To those unfamiliar, historic Wrigley Field is home to one of the city’s baseball teams – the Cubs.  Whether a fan of the Cubs, baseball in general or just a fun atmosphere, a day at the 100 year old ballpark is a must for locals and tourists alike.  You don’t need to enjoy baseball to enjoy a Cubs game – it is fun to just soak in the atmosphere while drinking and eating. (There are also tours of the stadium offered during the off season).

Enjoy One of Chicago’s Many Festivals

Chicago always has at least one or more festivals or events happening every weekend especially in the summer .  Some Chicago festivals are very well known and attract thousands of tourists, but there are many festivals and events in Chicago where you will mostly find locals. For great food, music and people watching, check to see if there are any festivals or events  going on while you are in town.

Walk The 606

The 606 is Chicago’s version of The Highline in NYC , an elevated trail goes through 2.7 miles of the city’s northwest side neighborhoods: Wicker Park, Bucktown, Humboldt Park, and Logan Square.  It is a bit off the beaten tourist path but it great place to walk, run or bike.  There are several access points so you can get off the trail to explore the various neighborhoods.

Where to Eat in Chicago

Chicago is known for its food so get ready to eat! Chicago is one of the best cities in the world for food and I could easily write a whole post just about the food! Although Chicago is famous for food like deep dish pizza and Chicago-style hot dogs – there is so much more great food in Chicago.  Don’t limit yourself to just deep dish pizza and hot dogs, but you should try those if you are visiting Chicago for the first time.

Lou Malnati’s and Giordano’s  are two of the best restaurants for deep dish pizza. Giordano’s can be found in several spots throughout the city including Navy Pier, near Michigan Avenue and near Millennium Park.

Many locals consider Pequods in Lincoln Park to have the best deep dish pizza in Chicago. Their version has a caramelized crust.

For Chicago style hot dogs (remember, no ketchup allowed) try Portillos , a popular chain.

Al’s Italian Beef (169 W Ontario St.) is famous for its Italian beef sandwiches.

For original Chicago-style popcorn head to Garrett Popcorn Shops, with a location near Millennium Park and Navy Pier.

To get an overview of the food scene consider a food tour:

Where to Stay in Chicago

Most people visiting Chicago stay in the downtown area including the Loop, River North, Gold Coast, Streeterville and Michigan Avenue since they are close to most of the major tourist attractions. If you are visiting during the weekend, the Loop is a great option as it is more quiet at night. River North (where I live) is close to nightlife and restaurants, but noise can be a problem especially during the weekends. Here are some of my top picks for the best hotels in Chicago :

The Peninsula Chicago.   If you are looking for a luxury hotel, The Peninsula Chicago is one of the best hotels in Chicago with a world renown spa and a half-Olympic length swimming pool overlooking the Chicago skyline. It has a central and convenient location right off the Magnificent Mile, close to shopping and less than a block from the Water Tower and 360 Chicago. Click here to see the latest prices and click here to read reviews .

Hilton Chicago/Magnificent Mile Suites.  Recently renovated all-suite hotel with fridge and microwave in room. Great location just steps from Michigan Avenue and one block from Lake Michigan.   Click here to see the latest prices and click here to read reviews .

ACME Hotel Company. This modern, stylish and unique hotel is located in downtown Chicago 2 ½ blocks from the Magnificent Mile in River North. Offers great value and great service. Click here to see the latest prices and click here to read reviews .

Best Western River North Hotel. Convenient located in the heart of River North close to the Chicago River as well as many restaurants and bars. Amenities include free high-speed Wi-Fi, deeply discounted parking, room service, fitness center, indoor pool and sun deck.  Click here to see the latest prices and click here to read reviews .

The Best Time to Visit Chicago

Chicago has plenty of things to do year round whatever the season. Summer is one of the best (and busiest) times to visit Chicago as the city comes alive and there are always outdoor festivals, concerts and events going on where you can take advantage of the warm weather. Restaurants and bars open their rooftops and sidewalk patios so you can dine outside. The temperature in the summer is usually hot but not unbearable (but some days can be very hot and muggy).

Winter can be very cold and snowy but some years can have mild winters with hardly any snow. Late November and December are busy with holiday events and festivities and the temperatures are usually still not that cold.  January and February tend to be the coldest months but attractions are less crowded. Even if you hate cold weather, there are enough indoor attractions to keep you entertained in Chicago during the winter .

Fall and spring are generally great times to visit Chicago – the popular attractions are not as busy as summer and the weather is usually more pleasant (but temperatures can be very unpredicable). The weekend before St. Patrick’s Day and the weeks during spring break can get very busy but the rest of spring is considered shoulder season.

Personally, I think the best time to visit Chicago is September and early October because students are back in school but temperatures are still warm but not as hot and humid as summer.

If you still need help deciding when to visit Chicago, check out The Best Time to Visit Chicago – A Month By Month Guide  for more details regarding weather and events by month.

Getting Around in Chicago

Chicago is an easy city to get around in with many public transportation options. Both Chicago airports – Chicago O’Hare (ORD) and Chicago Midway (MDW) – are connected to downtown Chicago by train.

For longer distances you can use public transportation , taxi, rideshare or rent bikes through Divvy (Chicago’s bike share program).

Taxis are plentiful and very easy to find downtown and at popular tourist attractions. You can also use the Curb app (for taxis) or ridesharing apps ( Lyft and Uber) to get around Chicago .

A hop on hop off bus is a great way to see all the attractions without having to figure out how to get around.

These are my top choices for the best things to do if you have 3 days in Chicago .

Planning a trip to Chicago? Check out more of my Chicago guides and itineraries:

• Best Things to Do in Chicago in the Summer
• 24 Hours in Chicago: A Perfect One Day Itinerary (From a Local)
• Most Instagrammable Places in Chicago
• Best Free Things to Do in Chicago
• Best Day Trips From Chicago

Related Posts

savvyglobetrotter

One comment.

Hi, I have also lived in Chicago and yes, although Summer is great, the best time to visit I’d also say it’s Aug/Sept. This is one, if not THE one, of the best places on Earth. I’d even say, if you can stay longer than 3 days in Chicago, do so. You are not going to regret it, since the city offers so much to do year round. Lovely post!

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Everything you need to know before visiting Chicago

Aug 15, 2023 • 8 min read

Use these top tips to help you make the most of your time in Chicago © Ryan McVay / Getty Images

I’ve lived in Chicago for more than 30 years, and these are the top tips I tell all of my visitors: take public transport, hit the neighborhoods and drink Malört at your peril.

Then you need to know about local sports culture, the ridiculous taxes and the ketchup rule… and that’s just for starters. I've gathered together all the top insider tips you need to ensure a smooth visit to the Windy City.

Plan on 3 to 5 days to visit

It’ll take you two to three days to see the highlights, like the Art Institute , Wrigley Field , Millennium Park and Willis Tower . Adding an extra couple of days to your visit allows you to move out of the center and into the neighborhoods , where Chicago’s true heart beats.

Pilsen and Logan Square welcome you with chowhound eats and vibrant street art. Bronzeville has galleries and soul food restaurants and Andersonville is a jazzy, cafe-laden LGBTQI+ hub. Hyde Park, Wicker Park and Humboldt Park are other troves of great restaurants and attractions.

Don’t drive, especially downtown

Driving in Chicago is no fun. Traffic snarls not only at rush hours but also most times in between. Road construction on the main highway through town has only added to the nightmare. What’s more, parking is hard to find and costs a fortune, particularly downtown near the sights – garages routinely charge around $45 per day. Ditch the car and use public transportation to spare yourself the annoyance.

Buy a Ventra Card for public transportation

It’s easy-peasy to make your way around Chicago on public transport – mainly the L trains, which run on both elevated and subway tracks. They’ll get you to most sights and neighborhoods into the wee hours. Buses pick up the slack in areas that the L misses.

To save time and money, buy a rechargeable Ventra Card to use on transit and add value as needed. Cards are available at any L station (including at the airports) and save around $0.75 per ride over disposable fare tickets. You can also download the Ventra app and buy a digital Ventra Card. The app has the bonus of providing L and bus times, too.

Whether using a plastic or digital card, simply tap it at the turnstile as you enter the L station or at the farebox as you get on the bus. If you’ll be riding three or more times per day, consider buying an unlimited ride day pass for additional savings.

Use the L to get to and from the airports

The aforementioned traffic is no joke. Taxis and ride-shares can take forever to get between the city and airports. Instead, use the L train. The Blue Line from O’Hare and Orange Line from Midway take 30 to 40 minutes and cost $3 to $5. Not only are travel times often quicker on the L, but it’s about 10 times cheaper than a cab.

Book museum and theater tickets in advance

Many museums, including the Art Institute , encourage tickets to be purchased online in advance from the museum’s website. A day or so prior should do it, unless there’s a blockbuster exhibit going on.

It’s also wise to book theater tickets beforehand, whether it’s for a world-class opera or booze-addled Shakespearean improv. A week ahead is usually plenty of time. Browse Hot Tix for same-week drama, comedy and performing arts tickets for half price.

Make restaurant reservations

Prepare to fork into platefuls of Michelin-starred comfort food and eat like royalty. Reservations are key, though, especially for weekend dining. Book through Tock , Open Table or Resy . A week or two in advance will work for most places, though hot spots such as Alinea and Girl & the Goat need to be reserved a couple of months out. Prime dining times are between 6pm and 8pm.

Pack a warm coat, but also a bathing suit

Chicago sits on the shore of vast Lake Michigan, which has a wild effect on the weather. It whips up heavy snow in winter and windy conditions year-round . Pack a warm coat, hat and sturdy shoes when visiting November through March. Even in summer, the temperature can drop fast, so bring a sweater when you head out for the day.

That’s not to say you shouldn’t also bring your bathing suit from June through August. The city has several beaches that beckon with sand and surf.

Where you stay depends on what you want to do

Downtown has loads of cool architectural hotels near the sights, but limited eating and drinking options after dark. Not ideal if you're looking to party but a good option if you're traveling with young kids.

Next door the Near North has hotels and evening action, but it’s pricey and a bit cookie-cutter. The West Loop, Lincoln Park, Lake View and Wicker Park all have abundant nightlife to keep you entertained into the wee hours. They’re not close to the main sights but are easy enough to access via the L. Book accommodations a month or two in advance, if possible.

Prepare for hefty taxes

A tax is levied on most goods and services in Chicago. It’s 17.4% for lodgings, 10.75-11.75% in restaurants and bars (it's higher the closer you are to downtown), and 10.25% for other items. The tax is typically not included in the price but added to the bill when you pay.

Cheer on the sports teams

Chicagoans are rabid sports fans – get to know the city's teams and you’ll make friends wherever you go in town.

Chicago’s two baseball teams inspire a diehard rivalry: the Cubs are the more moneyed North Side squad, while the White Sox are the blue-collar, working-class team on the South Side. Both have had great success in recent years. Then again, both have sucked in recent years, too! Usually, one team is up when the other is down.

The football-playing Bears ignite lots of fervor, but they’re typically not very good. They're followed by basketball's underachieving Bulls , hockey's try-hard Blackhawks , and soccer’s middling Fire .

Dress casual

Chicagoans dress informally. The apex of fashion for most men is a pair of khakis and a button-down shirt. Women's dress is similarly low-key, valuing comfort over high fashion. And don't worry about getting your best on for the evening. It's perfectly fine to wear jeans and casual clothes to dinner or the theater at night. No judgment here!

Never put ketchup on a hot dog

Weird but true: the red condiment does not go on local wieners. No one really knows why. One theory is that the famed Chicago-style hot dog – which is topped with mustard, sweet pickle relish, chopped onions, tomato slices, a dill pickle spear, sport peppers and celery salt – already has a perfect flavor balance. Adding ketchup is redundant and ruins the meaty harmony.

Grab a seat at the bar

Locals love to hang out in drinking establishments. Blame it on the long winter, when folks need to huddle together somewhere warm. Blame it on summer, when sunny days make beer gardens and sidewalk patios so splendid.

Beer is the drink of choice. No surprise given Chicago is home to more breweries than any other US city . Grab a seat in a neighborhood taproom, and you’ll be conversing about the Bears or the mayor in no time. You might even get offered a shot of Malört. It’s a local liquor famous for tasting awful . Downing one is a Chicago rite of passage.

Use the Pedway

Come wintertime, when the going gets tough and icy sleet knifes your face, head down to the Pedway . Chicago has a 40-block labyrinth of underground walkways, built in conjunction with the subway trains. The system isn’t entirely connected, and it’s confusing to figure out directions, but it’s also a dandy way to escape the elements. Look for "Pedway" signs above ground at points of entry.

Be courteous on the L

Let passengers get off the train before getting on yourself – wait beside the open door until everyone has departed. When you take the escalator in the stations, stand on the right side and walk on the left side.

Don’t smoke pot in public

Even though it’s legal to buy recreational marijuana throughout the city – at licensed dispensaries, cash only – you can only toke on private property. A backyard or balcony is fine, a car or cafe is not. Always check with the property owner to make sure they allow it.

As for cigarettes, you can’t smoke inside bars, restaurants and other public places, or within 15ft of the entrance.

Don’t let the headlines scare you away

Chicago has the unfortunate reputation of being the USA’s murder capital. While it’s true the city has the largest total number of homicides of any American municipality, it ranks much lower on the list when considered on a per capita basis .

Most of the violence is concentrated on the West and South Sides, where a handful of neighborhoods account for more than half of all shootings . These are communities where segregation and isolation have intensified inequality, and local gangs account for much of the bloodshed .

Overall, serious crime in Chicago has been dropping in recent years, according to city statistics. Still, it’s wise to take normal, big-city precautions, especially if solo at night. Many crimes involve cell phone theft, so be subtle when using yours. If driving, stay aware of your surroundings, as carjackings have been on the rise.

This article was first published Sep 16, 2021 and updated Aug 15, 2023.

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The 12 Best Things to Do in Chicago

Famously known as “the Second City” (meaning second in population to New York), I feel like Chicago is often overlooked by travelers. It sees a fraction of the visitors LA and NYC receive, which is a shame, as it’s one of my favorite cities in the world .

Chicago is chock-full of world-class institutions, Michelin-starred restaurants, awe-inducing architecture, and verdant parks. There is a lot to do here and the city has a really rich history. I think more people should visit.

Sure, the winters are brutal. But, come spring, Chicago blossoms into a dynamic urban landscape of street life, outdoor cafés, and sunny parks when locals take over the outdoors to enjoy the few months of nice weather. (I don’t think you can really beat Chicago in the summer.)

To help you plan your visit, here’s my list of the best things to do in Chicago:

Table of Contents

1. Take a Walking Tour

2. relax in grant and millennium parks, 3. take in some art at the art institute of chicago, 4. admire amazing architecture on a river cruise, 5. stroll down the magnificent mile, 6. visit the shedd aquarium, 7. take in some natural history at the field museum, 8. get a stunning view at 360 chicago observation deck, 9. feast on deep-dish pizza, 10. stroll the chicago riverwalk, 11. eat your way through the mexican eateries in pilsen, 12. watch an improv show, 13. have fun at navy pier, 14. catch a game at wrigley field, 15. feast in chinatown, 16. experience st. patrick’s day, 17. explore oz park.

One of the first things I do when I arrive in a city is take a walking tour. They’re a great way to see the main sights, get the lay of the land, and connect with an expert local guide who can answer all my questions. Free Chicago Walking Tours hosts regular free tours that can introduce you to the city. You’ll get to see many of the coolest buildings in the city while also learning about the history of Chicago. The tour lasts a few hours. Be sure to tip the guide at the end!

For a more unique tour, try the Gangsters and Ghosts Tour . You’ll learn all about Chicago’s dark side and creepy past as you explore the Chicago Loop. The tour lasts two hours and really talks about one of the pivotal times in Chicago’s history. Even if you’re not a history buff like me, you’ll get a lot out of it.  

Located downtown, these gigantic parks provide a great place to hang out, have a picnic, or go for a run. People play chess here when the weather is nice and, during the summer, there are a lot of free concerts and events here. The larger Grant Park stretches along Chicago’s waterfront, while Millennium Park is the subsection where the famous “Chicago Bean” sculpture is located. This iconic work of public art is a must-see. And, starting at noon on the first and third Saturdays from April through November, the Chicago Cultural Center hosts walking tours focusing on the art of Millennium Park. It’s really interesting. I love strolling through the park or just chilling here with a good book on a nice day.  

To beat the crowds, skip a weekend visit as the place gets packed. Instead, go on a Monday or Thursday evening (they’re open late on Thursdays). You’ll have the place virtually to yourself.

111 S Michigan Ave, (312) 443-3600, artic.edu. Open Thursday-Monday 11am-5pm (8pm on Thursdays). Admission is $32 USD ( $40 USD for advance skip-the-line entry ). Daily tours (included in the price of your ticket) are offered at 1pm and 3pm.  

Chicago is an architecture lover’s dream. The very best way to take in its famed buildings is via a river cruise . This way, you can sit back and cruise down the canals while an expert guide provides context for what you’re looking at. The guides will give you a detailed history of the architecture. Some of the buildings you’ll see on the boat ride include the Tribune Tower, 333 West Wacker, Navy Pier, the Willis Tower, the Wrigley Building, and Marina City, among others. All in all, there are about 50 structures to see on this fascinating tour, and I promise, it’s much more interesting than it sounds!  

Often nicknamed “Mag Mile,” this stretch along Michigan Avenue from the Chicago River to Oak Street is known for its upscale designer boutiques. In fact, rent here is the third highest in the US (after Fifth Avenue in New York City and Rodeo Drive in Beverly Hills). Even if you don’t want to blow your budget shopping, it’s still an experience to stroll along the avenue and take in the sights and the people, and enjoy the view of the Chicago River. There are several landmarks and attractions along the way too, including the 360 Chicago Observation Deck for expansive views over the city (more on this below).  

If you’re visiting the city with kids (or you’re a kid at heart), head to the massive Shedd Aquarium. It’s the third-largest aquarium in the Western hemisphere and home to over 32,000 animals. They have turtles, penguins, sea otters, snakes, sharks, and more. They really emphasize education here so you’ll learn a ton while you roam the different exhibitions. You can even pay extra to do things like feed penguins and sharks, and they also host all kinds of fun evening events (such as live music after hours). I absolutely love coming here. Just make sure to book your ticket in advance as they do get busy and sell out!

To beat the crowds, skip the weekend and visit during the week instead. Also, try and visit right when it opens (especially Wednesday-Friday). It’s usually quieter then.

1200 S DuSable Lake Shore Dr, (312) 939-2438, sheddaquarium.org. Open 9am-5pm Monday-Friday (9pm on Tuesdays), 9am-6pm Saturday, and 11am-6pm on Sundays. Tickets start at $37 USD. Admission can also be included with the Chicago CityPASS .  

One of the biggest museums in the world, the Field houses extensive collections spanning anthropology, geology, botany, and zoology. Some important collections include the displays of taxidermied animals, a wing dedicated to astronomy, and fascinating artifacts from ancient Egypt. I recommend planning to spend at least 3-4 hours to really take it all in.

1400 S. Dusable Lake Shore Drive, (312) 922-9410, fieldmuseum.org. Open daily 9am-5pm (last admission is at 4pm). Basic admission is $30 USD . Special exhibitions are an additional charge (which varies), though you can get an all-access pass for $43 USD.  

Chicago is a skyscraper city, including a few rather iconic towers. Located atop what was formerly known as the John Hancock Building and now (uninspiringly) called 875 N. Michigan, the 360-degree viewing deck a thousand feet up and allows visitors to get the best view of the Windy City and Lake Michigan. You can even grab a pint at the Cloud Bar, which serves beer from Moody Tongue, a local brewery.

If you’re a thrill seeker and want more than just the view, sign up for Tilt. This part of the observation deck is where you can stand in front of a glass window, which then tilts forward, until it appears you’re looking directly down at the street, 94 floors below.

Just make sure to check the weather before you go so you will actually have a view to enjoy. Additionally, if you want to beat the crowds, come early (before 10am).

875 N Michigan Ave, (888) 875-8439, 360chicago.com. Open daily 9am-11pm (the last entry is at 10pm). Admission starts at $30 USD ( get your tickets in advance for skip-the-line access ).

If you really want to indulge, hop on a Chicago Pizza Tour , on which you’ll get to sample all the varieties on offer in town. Tours start at $49 USD.  

Stretching from Lake Michigan to Lake Street, the 1.25-mile Riverwalk along the Chicago River makes for a fun stroll. Along the way, you’ll not only get fantastic views of the river and city, but you’ll encounter a legion of waterfront restaurants, cafés, and bars. There’s a ton of public art and green space too (great for picnicking and people-watching). It’s the perfect place to slow down and enjoy the moment in this Midwestern metropolis, but if you prefer a more active experience, there are also lots of aquatic activities here too (such as kayaking or taking a river cruise).  

The neighborhood of Pilsen was founded in 1878 by Czech immigrants, who named the area after the fourth-largest city in the Czech Republic, where pilsner beer was born. The Czechs may be gone now, but today Pilsen is Chicago’s main Latino neighborhood, particularly Mexicans from the Michoacán region. Today you can wander the area, eating some of the best tacos while taking in the vibrant street art.  

The Second City is one of the most popular and well-known improv troupes in the country. It’s where greats like Bill Murray, John Candy, Catherine O’Hara, Steve Carell, Tina Fey, and Amy Poehler all cut their teeth. They put on regular performances and also host all kinds of special events. They even host workshops and classes if you want to give improv a try yourself. Just be sure to get your tickets in advance as the most popular shows sell out fast.

230 W North Ave, (312) 337-3992, secondcity.com. Performances are held daily so check the website for what’s on. Tickets start at $35 USD.  

600 E Grand Ave, (312) 595-7437, navypier.org. Open Sunday-Thursday 11am-8pm and Friday-Saturday 11am-9pm (individual attractions and restaurants may have separate hours). Admission to the pier is free, though attractions charge their own fees ( the Centennial wheel is $21.30 USD , for example).  

Home of the Cubs, Wrigley Field, on Chicago’s North Side, is smack in the middle of town. It also happens to be one of the oldest baseball stadiums in the United States (it opened in 1914). If you’re in Chicago during the baseball seasons (April to October) and the Cubs are in town, do yourself a favor and go to a game. It’s one of the most intimate and atmospheric baseball stadiums in the country. If the Cubs are not in town, you can also take a 90-minute behind-the-scenes tour of the stadium.

1060 W Addison St, (773) 404-2827, mlb.com/cubs/ballpark. Tour dates and times vary depending on the season (check the website for availability). Tour admission is $30 USD. Tickets to see a game vary greatly but start at just $10 USD (for better seats at a popular game, expect to spend closer to $80-125 USD).  

Bring your appetite to Chinatown, where you can feast on cheap dim dum, do karaoke, or relax at one of the many tea houses. One of the oldest Chinatown’s in the country, over a third of Chicago’s Chinese population lives in Chinatown, making it one of the largest concentrations of Chinese-Americans in the USA. Don’t miss Ping Tom Memorial Park, and keep an eye out for colorful murals around the neighborhood. Some of my favorite places here are Hing Kee, MCCB Chicago, and Phoenix. &nbsp

The tradition began in 1843, when Chicago’s first Irish parade was held, but it wasn’t until 1962 that the dyeing of the river started, at the suggestion of a plumber’s union, which is still responsible for the green river each year, though it won’t divulge its secrets about what’s used (it’s environmentally friendly, though). Take a river cruise on the emerald waters or snap a pic from the sidelines and enjoy. This is one of the biggest days of the year here!  

This whimsical little park, located in the Lincoln Park area, was created to honor L. Frank Baum, the author of The Wizard of Oz . He lived in the area at the end of the 19th century, and when the city wanted to renovate the park they decided to do so in a way that honored Baum’s popular book.

There’s a playground named after Dorothy, a green space called the “Emerald Gardens,” and numerous life-size statues of popular characters from the musical adaptation, including the Dorothy, Toto, the Tin Man, the Cowardly Lion, and the Scarecrow.

Open daily 6am-11pm. Admission to the park is free.

Chicago doesn’t get the attention it deserves. I think it’s fun and perfect for a weekend getaway. And you really can’t beat the summers here either. With lots of interesting museums, plenty of green space, and some great eats, Chicago should be on every traveler’s list!

Book Your Trip to Chicago: Logistical Tips and Tricks

Book Your Flight Use Skyscanner to find a cheap flight. They are my favorite search engine because they search websites and airlines around the globe so you always know no stone is left unturned.

Book Your Accommodation You can book your hostel with Hostelworld as they have the biggest inventory and best deals. If you want to stay somewhere other than a hostel, use Booking.com as they consistently return the cheapest rates for guesthouses and cheap hotels.

Don’t Forget Travel Insurance Travel insurance will protect you against illness, injury, theft, and cancellations. It’s comprehensive protection in case anything goes wrong. I never go on a trip without it as I’ve had to use it many times in the past. My favorite companies that offer the best service and value are:

• Safety Wing (best for everyone)
• Insure My Trip (for those over 70)
• Medjet (for additional evacuation coverage)

Looking for the Best Companies to Save Money With? Check out my resource page for the best companies to use when you travel. I list all the ones I use to save money when I’m on the road. They will save you money when you travel too.

Want More Information on Chicago? Be sure to visit our robust destination guide on Chicago for even more planning tips!

Got a comment on this article? Join the conversation on Facebook , Instagram , or Twitter and share your thoughts!

Disclosure: Please note that some of the links above may be affiliate links, and at no additional cost to you, I earn a commission if you make a purchase. I recommend only products and companies I use and the income goes to keeping the site community supported and ad free.

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The Perfect 3 Days in Chicago Itinerary (2024 Edition)

• Last Updated: February 4, 2024

If you’re planning a long weekend trip to the Windy City and aren’t quite sure what to do, keep reading for our epic 3 days in Chicago itinerary!

While Chicago is the 3rd-largest city in the US, it’s often overlooked by travellers who jet for one of the coasts.

In my opinion, Chicago is the best city in the country. New York and LA are great and all, but I’ll gladly take the friendly Midwestern vibe of Chicago instead.

Situated on Lake Michigan, the Chicago skyline is one of the most beautiful in the world. After all, it was here that the first skyscraper was built in 1885!

There’s so much going on here that you could spend a lifetime there and never run out of things to do.

With a solid Chicago itinerary, you can definitely check out the best of the city in 3 days. Let’s get to it!

Table of Contents

When to Visit Chicago

Chicago citypass, getting around chicago, loop walking tour, chicago hot dog, millennium park, art institute of chicago, willis tower, dinner and drinks, museum campus, riverwalk or river cruise, magnificent mile, chicago deep dish pizza, choose your own adventure, museum of your choice, 360 chicago, lincoln park, best hostel in chicago – hi chicago, best mid-range hotel – congress plaza, best luxury hotel – peninsula, brunch/lunch, how to spend a perfect 3 days in chicago itinerary.

Our 3 days in Chicago itinerary includes:

• Shedd Aquarium
• Skydeck Chicago
• Field Museum
• Adler Planetarium
• 360 CHICAGO Observation Deck
• Navy PierMuseum of Science and Industry
• Ferris Wheel
• Crown Fountain

Looking for more awesome things to add to your Chicago itinerary? Be sure to read our guide to the best things to do in Chicago !

Travel Tips for Visiting Chicago

The first step in figuring out what to do during your 3 day Chicago itinerary is planning when you’ll visit.

Winter in Chicago can be painfully cold, which can definitely put a damper on your trip. Unless you enjoy frigid temperatures and cold, biting wind, I recommend skipping out on December-March.

Your best bet is to visit Chicago between May and October. It gets hot and crowded in the summer, but there’s so much going on that it’s worth dealing with those minor inconveniences.

Read Next: Don’t miss out on the best Chicago day trips !

Another huge tip I have before you visit Chicago is to purchase a Chicago CityPASS .

Essentially this is just a multi-use ticket that actually saves you a bunch of money (50% to be precise!) on many great Chicago attractions.

You buy the pass for USD$109, and it includes access to the following:

• Skydeck Chicago and
• Adler Planetarium or the Art Institute of Chicago
• 360 CHICAGO Observation Deck or the Museum of Science and Industry

Best of all, those entrances are mostly express or premium tickets included with the CityPASS , meaning it not only saves you money but saves you time as well.

We highly recommend you pick one up when using our Chicago itinerary to make the most of your time in the city.

Thankfully, getting around Chicago is a breeze thanks to the CTA network of train and bus lines. Chicagoans refer to the train as the “L” because it’s mostly on “el-evated tracks.”

If you’re spending 3 days in Chicago, your best bet is to just pick up an unlimited CTA pass. These cost $20 and are added to a Ventra card.

You can pick up a Ventra card at vending machines for $5 and it’s credited back to your account after you register the card. Read all about getting around Chicago on the CTA website .

You can count on the CTA getting you as far south as the Museum of Science and Industry all the way north to Lincoln Park.

Or consider jumping on and off the open-top bus that will take you all over the city!

In the city center, lots of Chicago attractions are all within walking distance as well.

Now that some of the logistics are taken care of, let’s get this show on the road for your 3 day Chicago itinerary!

Day 1 – Morning

For day 1 of your Chicago itinerary , you’ll need to hit the ground running if you want to maximize your time.

Get a nice early start, crush a substantial breakfast and some coffee, and get ready to rock.

The best way to kick-off your Chicago itinerary is by taking a walking tour of the Loop. This area of downtown is where you’ll find a majority of the sights in Chitown.

You have several options for exploring the Loop. If you enjoy meeting people and getting the insight of a local guide, you can sign up for one of the many options with Free Tours by Foot .

If it’s your first time in Chicago I suggest joining their 10 AM tour of the Loop and Millennium Park. Or if you’re really into architecture, check out their 10:30 Birth of the Skyscraper tour. Both are excellent options!

Those who prefer a DIY approach can check out the many self-guided tours of Chicago from MetroWalkz. This Architecture/Loop tour makes for a fantastic introduction to the city and is pretty easy to follow.

Whichever option you choose, you’ll get to see some of the most iconic places in the city in just a few short hours. A few of the highlights include the historic start of Route 66, the great Chicago Theatre.

READ NEXT: While you’re exploring the Midwest, be sure to check out the best things to do in Minneapolis, Minnesota !

Day 1 – Afternoon

At this point, the order in which you do things depends on which type of tour you chose. You can be flexible, as it’s a short walk between the next couple of destinations.

Before we move along with the 3 day Chicago itinerary, it’s time for lunch! If you’re down in the Loop and you want to try a local favourite, the choice is easy…

There are countless restaurants to choose from in the Loop, but you don’t want to travel all the way to Chicago to get stuck eating at some overrated chain or overpriced tourist trap.

Al’s is a classic local joint serving up the famous Chicago style hot dogs and their specialty Italian beef sandwiches.

One thing to know, a Chicago dog is an all-beef dog on a sesame seed bun. It comes topped with tomato, chopped onions, pickled peppers, relish, a pickle spear, and yellow mustard. Quite simply put, it’s heaven on a bun.

I would be remiss if I didn’t also mention Portillo’s. They also make one of the best Chicago style hot dogs out there.

While they’re a bit out of the way for today’s itinerary, keep them in mind if you’re craving another hot dog during your 3 days in Chicago (and trust me, you will).

Read More: Spending time exploring the Midwest? Be sure to check out our post on all of the best things to do in Kansas City !

Even if you visited on your walking tour, it’s worth it to double back to Millennium Park for further exploration.

There’s a lot of cool stuff to see here, including the Crown Fountain and the Cloud Gate.

The latter is commonly referred to as “The Bean” and is one of Chicago’s most popular places to take photos in the city. Don’t forget to snap that quintessential Chicago shot for the ‘gram and keep on moving.

Other Chicago attractions you must see in Millennium Park include the Jay Pritzker Pavilion, the BP Pedestrian Bridge, the Chicago Cultural Center, and the Lurie Garden.

You can easily spend a couple of hours in Millennium Park, especially on a nice day.

Buckingham Fountain and Grant Park are within this same area as well if you want to keep exploring on foot.

While there’s plenty of amazing public art in the Loop, you can’t top the collection at the Art Institute of Chicago. Art lovers will definitely want to include this on their 3 day Chicago itinerary.

Tucked away on Michigan Avenue on the south end of Millennium Park, the Art Institute of Chicago has a seriously impressive collection here and there are always new exhibits featuring modern and contemporary art.

Make the most of your Chicago CityPASS to gain fast entry into the Art Institute of Chicago.

The museum is open daily from 10:30 AM to 5 PM and stays open until 8 on Thursdays.

Day 1 – Evening

Before the day turns into night, it’s time to hustle over to your next destination of your 3 day Chicago itinerary. Try to time it just right so you make it there about an hour before sunset. Trust me, it’s worth it!

Whether or not you hit the museum, your next stop should be the Willis Tower. This is one of Chicago’s most iconic skyscraper in the city that invented them!

Formerly known as the Sears Tower, this was the tallest building in the world for 25 years. It stands at 442 meters (1,450 feet) tall and is currently the 2nd-tallest building in the US.

If you plan to visit Chicago in 3 days, you definitely need to check the Willis Tower off your to-do list.

Head to the 103rd floor to access the Skydeck Chicago and step out onto “The Ledge” – a glass balcony that lets you look straight down. You’ll want to see views of the city from this spectacular perspective!

Don’t forget, the best time to go to the Willis Tower is just before sunset. It stays open until 10 PM from March through September and tickets cost $25 for adults and $17 for children.

Once again though, no need to pay extra for a ticket, because the entrance to the Skydeck Chicago is included with your CityPASS .

To celebrate making it through a massive day 1 of the Chicago itinerary, it’s time for dinner and drinks! When it comes to wining and dining, the world really is your oyster in the Loop.

After such a big day, you may want to call it a (somewhat) early night. We’ve still got a lot of ground to cover with this 3 days in Chicago itinerary! Of course, if you want to go out and rage, go for it!

Day 2 – Morning

If you don’t have breakfast included at your hotel, I highly advise you to start day two off at Yolk’s South Loop location.

This is the perfect spot to load up with a big breakfast and coffee before another big day in the city. Go ahead and carb up – there’s going to be a lot of walking today!

After breakfast, walk across the street to check out Agora – a sculpture composed of 106 headless figures.

Keep walking east towards Lake Michigan to reach the Museum Campus. Here you’ll find the Field Museum, Shedd Aquarium, and the Adler Planetarium.

With just 3 days in Chicago, you’ll probably want to just visit one. Having been to all three, I’ll cast my vote for the Field Museum.

There are so many cool exhibits at the Field Museum and they’re always changing.

At the moment, they have: Inside Ancient Egypt, Bird’s of America, and Brewing Up Chicago, among others. Check their website to see what’s going on before you visit.

Tickets for the Field Museum cost $26 for adults and $19 for children for basic admission.

If you got the CityPASS, your admission is included in all three, unless you hit the Art Institute on day one. If you’ve got the pass, you might as well hit the aquarium as well.

To be honest, the aquarium is pretty sweet. Even if you don’t have the CityPASS, you should probably try to squeeze it in.

Tickets are $40 for adults and $30 for kids and you’ll definitely get your money’s worth.

Day 2 – Afternoon

There are a few cafes and food stands around the museum campus, so go ahead and grab a snack and a drink before powering on.

This is one of those days where it’s best to have a big breakfast and dinner and just graze during the day. When you’re trying to cross off so many things to do in Chicago in 3 days, you gotta keep moving!

The museum campus is the southern part of Grant Park. Known as “Chicago’s Front Yard,” this massive green space is to Chicago what Central Park is to NYC.

Take a stroll through the park to see such landmarks as the Buckingham Fountain, the Rose Garden, and the Seated Lincoln Statue. There are plenty of benches if you need to sit down and chill for a bit.

Grant Park also hosts some of the biggest events in the city, such as the Taste of Chicago and Lollapalooza.

Some are free and others cost hundreds of dollars, so be sure to check the calendar of events to see what’s happening before you book your trip.

Hug the coast and keep walking north along the Lake Michigan until you reach the Riverwalk. This scenic pedestrian path along the Chicago River is the perfect place for a leisurely stroll.

If your feet are feeling a bit tired from all the walking, you can enjoy the spectacular Chicago architecture on this fantastic river cruise instead .

Taking in the sights along the Chicago River is definitely one of the top things to do in a 3 day Chicago itinerary.

Wendella Boats has an architecture river cruise that comes highly recommended. Make sure you have your camera for this one, as you’ll get some epic views of the city.

Day 2 – Evening

I’m sure you’re ready to eat your hand by now, but you’ve just got to soldier on for a bit longer. Trust me, it’s going to be worth the wait!

On the other side of the Chicago River, you’ll find the Magnificent Mile, a short stretch of Michigan Avenue in downtown Chicago. This is the city’s premier commercial district, full of high-end shops, nice restaurants, and boutique hotels.

Along the Magnificent Mile, you’ll also see several historic skyscrapers, such as the Wrigley Building, Tribune Tower, and the Old Watertower.

The latter is home to the City Gallery, which has Chicago-focused photography exhibits. It’s totally free to visit, so you may as well check out while you’re in the area.

Even if you’re not doing any shopping, it’s worth a quick stroll along the famous Michigan Avenue. That’s because it’s leading you to…

You had the hot dog on day one, so it’s time to dig into some Chicago-style deep dish pizza.

Since it’s cooked in such a deep pan, a Chicago-style deep dish pizza can be stuffed with mountains of cheese. Of course, you can add whatever other toppings you like as well.

Now you see why I’ve been torturing you by making you walk around all day waiting for dinner! This deep dish pizza is seriously delicious and filling, so I wanted to make sure you could at least have a few slices.

There are plenty of places cooking up Chicago-style deep dish pizza, but I brought you here because two of the best are easily accessible.

Get to the corner of Michigan and Superior and you have an important choice to make. Take a left and you’ll go to Giordano’s. Hook a right and you’ll be at Gino’s East.

Just go ahead and flip a coin because you win either way. Both places are legendary for their deep dish pizzas, so you really can’t go wrong.

Not far from the Magnificent Mile, you’ll find Navy Pier. If you’re spending 3 days in Chicago on a long weekend, this is the perfect place to be on a Saturday night.

First up, you can take a ride on the Centennial Ferris Wheel. Tickets cost $18 for adults and $16 for children, but you can save a few bucks if you book online .

From the end of May until the end of August, Navy Pier also hosts bi-weekly fireworks shows. These happen on Wednesdays at 9:30 PM and Saturdays at 10:15.

To take in the spectacle, you can find a spot to stand on the Navy Pier or sign up for an evening cruise. Enjoying the fireworks as you cruise around is a great addition to your Chicago itinerary.

If you have any gas left in the tank after all of the activities at the Navy Pier, congratulations! I just ran you ragged all over Chicago on day two. That’s why it’s time to choose your own adventure!

For many, that will probably involve grabbing a casual drink from the hotel bar and getting some sleep. That’s totally fine. I’m getting to the age where that sounds like a perfect Saturday night!

For the young whipper-snappers among us, you’re probably itching to enjoy a big night out on the town. Go for it, you crazy kids!

Your options are endless. There’s live music of all varieties, comedy clubs, and just about every type of bar under the sun.

Whether you’re looking for a speakeasy that whips up creative cocktails, a classy wine & jazz joint, or just a good ole’ fashioned dive, you can find it in Chicago.

In this part of the city, one of my personal favourites is Three Dots & a Dash. This awesome tiki bar has an impressive selection of cocktails that will transport you to the Caribbean in no time.

If you’re going to go hard one night, this is the one to do it! Bars in Chicago typically close at 2 AM, but there are several that stay open as late as 4 on the weekend. You’ve been warned…

Day 3 – Morning

How early the last day of your 3 day Chicago itinerary starts depends entirely on how late your night went!

Those who already regret ordering that last round may need to sleep in a bit and smash a greasy brunch, while the go-getter set who actually slept will be up and at them. Life is all about choices, people!

Whatever you did the night before, get some food and caffeine in your system and get out there to wind down this 3 day Chicago itinerary.

Our third and final day in Chicago starts off with a leisurely museum visit. Within a few blocks of each other, you can take your pick between three excellent museums.

Art enthusiasts will gravitate towards the Museum of Contemporary Art, which highlights post-WWII art.

Those more interested in architecture and antiques may want to hit the Richard H. Driehaus Museum. It’s in a restored 19th-century mansion and brings you right back to the Gilded Age.

Chicago is very much a sports city, as people here are very passionate about their teams. Check out the Chicago Sports Museum, which is full of memorabilia and plenty of fun exhibits.

I know I already sent you to the Willis Tower on day one, but it’s still worth a trip to John Hancock’s 360 Chicago on Michigan Avenue.

This observation deck on the 94th floor of the John Hancock Building provides a whole different perspective on the city that you will definitely want to see.

Plus, if you bought a CityPASS your admission to the John Hancock building is already included! If you didn’t grab the pass, a ticket is $25 for adults or $15 for children.

Those who are feeling adventurous (and not hungover) may want to take a ride on Tilt – Chicago’s highest thrill ride.

If you need some hair of the dog instead, you can grab a ticket that includes your choice of adult beverage. Sunday Funday!

If you don’t purchase the Chicago CityPASS consider purchasing this ticket to enjoy the views from the 94th floor of the John Hancock building’s 360 Chicago.

Day 3 – Afternoon

Once you come down from 360 Chicago in John Hancock building, you have plenty of options for lunch. Within a few blocks, you can find Cuban, Vietnamese, Mediterranean, and the Chicago staple of deep dish pizza.

If you want a lunch with a view, consider eating at The Kennison. This upscale bar and restaurant offers sweeping views of Lincoln Park. The menu is modern American and they have lots of amazing cocktails and drinks.

Hop on the bus, order an Uber, or walk 30 minutes to our next destination – Lincoln Park.

There’s a lot to do in this huge park on the shores of Lake Michigan. North Avenue Beach is at the south end.

On a beautiful day in Chicago, it’s hard to beat lounging on the beach and swimming in the lake. You can also play some beach volleyball and rent a SUP or bike if you want some more activity.

In the middle is the Lincoln Park Zoo, which is totally free to visit. Sightseeing gets expensive, so this awesome free attraction is definitely one of the top things for any Chicago itinerary.

After such an action-packed 3 days in Chicago, you should definitely just take it easy and enjoy all that Lincoln Park has to offer. You’ve covered some serious ground in a short time, so congrats on that!

Day 3 – Evening

At this point in the journey, you have absolutely crushed 3 perfect days in Chicago. Order a celebratory drink or two and enjoy your last evening in the city!

What you choose to do with your final night all depends on when you’re visiting and what your interests are. That’s why it’s time once again to…

In a perfect world, the Cubs would be playing a night game while you are visiting Chicago. You could head north to Wrigley Field and enjoy America’s pastime at the 2nd-oldest ballpark in the country.

The Cubs play about 80 home games between April and September, so there’s a good chance they’ll be in town when you are. Even if you’re not a baseball fan, I recommend hitting a game if at all possible.

Chicago actually has two MLB teams. But the White Sox ballpark is way south of where you’ll be on day three and not worth the trip if you ask me.

If you’re making a trip to Chicago between October and April, you may be able to catch the Bulls (NBA), Blackhawks (NHL), or the Bears play a home game. Check their schedules to see what’s going on when you’re in town.

Those who prefer a good laugh can head back to the south end of Lincoln Park. Just a block away, you’ll find three of the city’s best comedy clubs – Second City, UP, and Zanies.

I pretty much always travel to Chicago for live music, so you know I’m going to toss that in here!

The city has an epic music scene and there’s always something playing here. Whether you’re into rock, hip-hop, jazz, electronic, blues, pop, or whatever it is you wacky Millenials listen to these days, there’s a show for you.

I usually check Jambase to see what shows are playing.

Congratulations, my friend. You made it through an insane 3 days in Chicago itinerary and experienced the best that the Windy City has to offer.

I’d say that calls for a toast! If you want to finish up with a true Chicago experience, order a shot of malort. This infamous Chicago liquor is pretty hard to describe, so I’ll let its label do the work:

“ Malort has the aroma and full-bodied flavor of an unusual botanical. Its bitter taste is savored by two-fisted drinkers .”

I’m not going to sugar coat it – this stuff is awful. It’s a rite of passage here in Chicago, though. Eat the hot dog. Drink the malort. Praise be to Ditka. You’re now a little bit Chicagoan.

After you finish that putrid shot of malort, switch to a delicious Chicago craft beer. There are plenty of choices here, including Lagunitas, Revolution, and Goose Island.

I hope you enjoyed this massive tour of Chicago!

From Navy Pier, to Millennium Park, the Chicago riverwalk, the famous Chicago hot dogs and more, visiting Chicago is never dull.

Hopefully this 3 day Chicago itinerary has been inspiring and gives you an idea of what to do in the Windy City.

Chicago Itinerary Travel Guide

Now that you know what to do with a long weekend in Chicago, I’ve gone ahead and put together a mini-guide to this awesome city to help you decide where to stay, where to eat, and of course where to drink!

Where to Stay in Chicago

You’re probably wondering where to stay, especially if it is your first time in Chicago.

Most first-time visitors choose to base themselves in downtown Chicago, and for good reason. Here are countless options for accommodation, sightseeing, dining, and nightlife.

As you might expect, staying downtown comes with a price tag. Other popular places to stay that are a bit cheaper include River North, Lincoln Park, Bucktown, and Wicker Park.

When it comes to places to lay your head, Chicago has it all. The city has 5-star luxury hotels, quaint B&Bs, dingy motels, fun hostels, and plenty of options on sites like Airbnb.

Here are a few options to suit all budgets:

Hostelling International is a trusted name in backpacker accommodation, and their downtown Chicago location is definitely the best hostel for visiting Chicago.

They have several different options for both private and dorm rooms. You can get a bunk for under $40 a night here – a steal for this fantastic location.This includes a free breakfast, and they also have free walking tours during the day and free activities at night.

That’s not all, though. They’ve also got a huge lounge with a ping pong table and a TV room with plenty of movies. Best of all, this hostel is environmentally-friendly. They have reusable products in the kitchen and recycling points all around the building.

This historic downtown Chicago hotel dates all the way back to 1893. Don’t worry – it’s had several updates over the years!

You really can’t beat the location of this place. I usually stay with friends in more residential neighbourhoods, but this is my go-to spot when I want to be in the middle of all the action.

From here, you’re just across the street from Grant Park. Many of the rooms here even boast a nice view of Lake Michigan. With rooms starting as low as $115 a night, it’s a pretty awesome deal staying here.

The 5-star Peninsula Chicago was recently named the 2nd best hotel in the country by US News & World Report. This place is fancy, people!

It’s located right on the Magnificent Mile, so it’s surrounded by high-end shops. This is definitely where the fabulous people stay.

In addition to the super swanky rooms, you can enjoy the hotel’s three different restaurants and its impressive fitness centre.

Taking up the top two floors of the building, it features a 25-meter pool and an award-winning spa. Rooms start at around $600 a night here.

Where to Eat and Drink in Chicago

I’m very fortunate to have a good friend who is heavily involved in the hospitality scene in Chicago.

I reached out to him to get a list to add to this guide. He’s never done me wrong with food & drink recommendations, so you can take these to the bank the next time you visit Chicago!

• Dove’s Luncheonette
• Joe’s Stone Crab: It’s a steakhouse and it’s hard to get into at night, but if you go for boozy brunch it’s great.
• Parson’s Chicken & Fish: Not really brunch but just a great people-watching patio.
• Big Star: Chicago classic taco joint with highly sought after patio
• 3 Arts Club

• Bavette’s Bar & Boeuf
• The Roister
• Green Street Smoked Meats: A great BBQ joint and High Five Ramen is below.
• Maple & Ash
• Nico Osteri
• Billy Sunday
• Aviary (try to get down to the office)
• Violet Hour
• Start at Scofflaw and work your way over to Best Intentions
• Longman & Eagle 
• The California Clipper: Been around since before prohibition!

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Sasha and Rachel

Hi, We’re Alesha and Jarryd!

We’ve been traveling the world together since 2008, searching for the planet’s best destinations and adventures.

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I would love to visit Chicago in 2024! This itinerary looks perfect!

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3 Days in Chicago: The Ultimate Weekend in Chicago Itinerary

Chicago is a vibrant city that feels very alive, and with the perfect 3 days in Chicago itinerary, it’s possible to sample the best of the city over a long weekend!

The city is always on the move, and there isn’t an hour in the day that you won’t find at least 10 unique and adventurous things going on around town.

Music and food festivals pull out all the stops in Chicago, on top of the arts and cultural events that dot the city throughout the year.

Are you into food and drinks, lake views, and most of all, fun? Then Chicago is the place to be. There is enough here to explore for months, and we are going to pack all of the best events and activities into a 3 day long weekend itinerary to experience the essence of Chicago. 

Note: this Chicago blog post was written for Our Escape Clause by former Chicago locals Zach & Julie Ruhl, the travel couple behind Ruhls of the Road . Thanks for joining us, guys!

Table of Contents

Day 1 in Chicago Itinerary: The Bean, Skydeck & Great Chicago Food

Day 2 in chicago itinerary: lincoln park, wrigley field & beyond, day 3 in chicago itinerary: magnificent mile, navy pier & an afternoon adventure, where to stay for 3 days in chicago, where to eat during your chicago weekend getaway, getting around during 3 days in chicago, when to spend a long weekend in chicago.

Some links in this post may be affiliate links. If you make a purchase through one of these links, we may earn a small commission at no extra cost to you. Please see our disclosure policy for more detail.

Chicago is an enormous place. The city covers miles in each direction, with awesome things to do located all over the map. Therefore, this Chicago itinerary is going to thoughtfully take you from place to place, minimizing travel time and maximizing adventure.

Your first day in any new city should no doubt include some of the most signature sightseeing highlights there–and this Chicago itinerary is no exception, starting with a popular activity that is relatively new in Chicago: the Riverwalk. The current version of the Riverwalk was completed in 2017 and is an excellent place to start your Chicago weekend getaway.

Start your weekend in Chicago with a walk on the Chicago Riverwalk.

The Chicago Riverwalk starts at Wolf Point, near where the Chicago River turns from East/West to North/South. From there, the Riverwalk continues for over a mile, to the point where the Chicago River meets Lake Michigan.

Along this beautiful walk, you’ll pass a few awesome cafes and restaurants. This is a great place for a morning coffee, watching the morning hustle and bustle of America’s third-largest city. On top of that, the morning walk counts as your exercise for the day!

If you fall in love with the Riverwalk, then come back for a happy hour one evening. Riverside wineries and bars open up during the evening, complete with sets of outdoor games, live music, and some great entertainment! 

Check out Millennium Park.

At the end of the Chicago Riverwalk, you’ll reach Lake Michigan. Turn right here and head South to Millenium Park, where you’ll find an excellent location for soaking in the Chicago skyline from a beautiful park in the huge city center.

Millennium Park is an awesome Chicago sightseeing destination for two reasons. First off, it is just a great park full of fun things to do in Chicago !

There is an awesome playground for kids to play on, a great dog park for your four-legged friends, a huge green space to sprawl out for a picnic, a live music amphitheater, the Crown Fountain with a reflecting pool, endless gardens, and so much more!

You could spend a whole day at Millenium Park and not grow bored.

The second reason Millenium Park is so great is its proximity to everything. The park is great, but what makes it so impressive is that you are literally in a natural oasis amidst the concrete jungle of downtown Chicago.

Look around you while in the park, and you’ll see the towering structures of the Willis Tower, the Aon Center, and the rest of the enormous Chicago skyline.

Snap photos at The Bean.

At the edge of Millenium Park is The Bean, AKA Cloud Gate, Chicago’s most photographed (unofficial) monument.

The Bean is a huge monument, standing over 30 feet tall and 60 feet long, that is made of polished chrome and has no visible seams. This structure is truly unique and is an awesome downtown Chicago sight. 

The Bean is perfectly reflective, and due to its shape, the reflections can make for very fun images. It is essentially a gigantic magic mirror, placed in the middle of a bustling downtown environment.

Spend some time enjoying the fun reflections you can see as you walk in a circle around and under The Bean, then head for some food.

Downtown Chicago should have plenty of options on your way to your next stop: the Willis Tower. 

Admire views of Chicago from the Willis Tower Skydeck.

The Willis Tower is Chicago’s tallest building and the second tallest in the United States. At one point, this skyscraper was even the tallest building in the whole world, and held that title for 25 years! There’s no doubt that this is a must-see spot on any 3 day Chicago itinerary.

When you visit the Willis Tower, there are really two things you need to do. First off, admire the size of this monstrosity from below. The building literally reaches into the sky, and from the bottom seems impossibly huge. Walk around it marveling upwards, just make sure to lose your attention and wander into the city streets!

The other way to see the Willis Tower is, of course, from the top. The Skydeck is at the very top of the building, where you can see Chicago stretch beneath you for miles and miles in each direction into the horizon.

If you have the stomach for it, there is even a glass-bottomed section where you can literally step out into the sky, or at least it looks that way. From the glass floor, you can see down over 1,000 feet to the streets beneath you. This is quite an incredible experience and one that you won’t get anywhere else in the United States!

Book your Skydeck tickets for the Willis Tower today!

Finish your first day in Chicago in West Loop on Randolph.

The West Loop is an up-and-coming neighborhood in Chicago. This area seemingly has a great new restaurant pop up each week and has some of the most delicious food and one of the most fun atmospheres in the city.

Randolph Street in the West Loop is the culinary center of the neighborhood and is where you should head for dinner and drinks on your first day in Chicago. If you have the time and energy, the very best activity is to have a drink at a few different places, hopping from place to place and soaking up as much of this wonderful neighborhood as you can.

Each restaurant will have a unique vibe and atmosphere, so keep hopping around until you find the one you love best.

Want to make sure you experience the best food in the neighborhood? Add this popular West Loop Food Tour to your Chicago itinerary!

Close out your first night in Chicago at an Irish pub.

Chicago has a huge Irish population, and therefore quite a few Irish pubs located around the city. Our best recommendation is to find one close to your hotel and pop in for a Guinness as a night-cap. Enjoy the Chicago atmosphere, and then head to your hotel to get some sleep before heading off on your second day’s worth of fun things to do in Chicago!

Day 2 in Chicago is going to be a day full of exploring Chicago’s famous North Side. The North Side is awash with classic Chicago food options (Chicago loves its food…) as well as awesome sites to see and things to do. First up is the famous Lincoln Park.

Start the day with a stroll through Lincoln Park.

Lincoln Park is a huge and sprawling greenspace alongside Lake Michigan for 7 long miles. This is, in fact, the largest park in all of Chicago! And it also may very well be the most beautiful.

Alongside Lake Michigan, Lincoln Park has a few different beaches, as well as seemingly endless biking and walking trails. If you would rather bike than walk, then there are many bike rental options scattered all around the park, and around Chicago as a whole.

While strolling or biking through Lincoln Park, make sure to stop and see the Belmont Rocks, North Pond, and the Signal of Peace Monument. Along the way, admire the natural beauty and enjoy the sounds of birds singing as you bring on your second day in Chicago.

Soak up the sun at North Avenue Beach.

North Avenue Beach is one of Chicago’s largest and most popular beaches. Located right alongside Lake Michigan, this vast expanse of white sand makes for a great place to enjoy the beautiful Chicago summer sun.

If you are traveling with a group, then there are opportunities for some beach volleyball at North Avenue Beach! At the beach, you can rent a net and a ball (rentals are by the hour) and play some volleyball on the sand in view of the Chicago skyline!

While at North Avenue Beach, you must make a stop at the famous beach house that is shaped like a boat. This is also the location of Castaways, a bar and grill on the roof of the beach house serving yummy drinks with an incredible view. 

Head to Wrigley Field & Wrigleyville.

You can’t visit the North Side of Chicago and not see Wrigley Field. As one of the most famous baseball stadiums in existence, and the home of the Chicago Cubs, this is a must-see stadium, especially for sports fans.

Wrigley Field is located right in the heart of Wrigleyville on the North Side. Surrounded by residential areas and a huge bar and restaurant scene, this area is a magnet for good times, especially when the hometown Cubs are lacing up their cleats for a game.

If you are fortunate enough to be in Chicago while the Cubs are playing, head to Wrigley just for the experience of people watching and cheering on the hometown team. If you’d like, you could even try and buy some tickets, and usually, you can get a good deal on seats if you are okay purchasing them after the game is already in the 2nd or 3rd inning.

Wrigleyville, the neighborhood surrounding Wrigley Field, is an excellent place to hang out, have a drink, and hop around a few of the local establishments. Each of them has a great atmosphere, delicious, food, and of course a wide array of beers on tap.

Sample some Malort.

Malort is a Chicago specialty liquor and is something anyone over 21 should try when they visit the Windy City.

The liquor itself is not good because of taste, in fact, it tastes pretty bitter, and most people find it awful. However, it is all about the experience of trying something the locals love! If you’d like to experience the local culture of Chicago, then you have to try Malort at least once.

Finish the Day at the John Hancock Center Signature Lounge.

The John Hancock Center is the best building in Chicago. That may be a controversial opinion, but it is so true. The enormous slanted walls of the Hancock reach over 1,000 feet into the Chicago sky, with huge beams in a crisscrossing X pattern the entire way up. The building is an architectural masterpiece and is a wonder to see from the base.

The best place to experience the Hancock Center, however, is not from the base. It is from the Signature Room.

What is the Signature Room? It is an incredible 95th-floor bar and restaurant with an absolutely stunning view of Chicago. The Signature Room offers a 360-degree view of Chicago from above and is especially breathtaking as the sun sets and the sea of lights emerges beneath you.

Experiencing an evening at the Signature Room is a wonderful experience, and will be a highlight of your visit to Chicago. If you are visiting on a budget, just order a drink here, as dinner can be expensive!

Day 3 is going to be spent exploring more awesome sites and destinations in downtown Chicago. It is going to be a day where you can see as much as you want, and take it all in at your own pace. Choose your own adventure and make today special as you finish up your long weekend in Chicago!

Walk down the Magnificent Mile.

Start the day with a trip down the Magnificent Mile. This is a section of Michigan Avenue that is the retail center of Chicago. The street is lined on both sides with tons and tons of flagship stores, boutiques, and shopping malls.

Along the Magnificent Mile, in addition to all of the premier shopping, there are a few awesome sights you’ll see during this part of your Chicago weekend getaway.

The Wrigley Building is an awesome structure located right where Michigan Avenue meets the Chicago River. The Tribune Tower and the Chicago Water Tower are also wonderful landmarks along this stretch.

Explore Navy Pier.

Just a few blocks from the Magnificent Mile is Navy Pier, an absolute must-visit destination on any Chicago visit. The Navy Pier is, as the name suggests, a large pier, formerly used by the Navy, that extends straight out into Lake Michigan. 

These days, Navy Pier is an awesome destination that is used for a wide variety of attractions. First off, there is almost always some form of live entertainment or shows that are happening over a weekend at Navy Pier. On top of that, the pier is lined with awesome bars and restaurants, as well as shops and boutiques.

The view from the end of Navy Pier is excellent. First off, you’ll get to see the vast expanse of Lake Michigan on 3 sides of the pier. However, when you look back at the city, you’ll get a view of the full skyline including the Willis Tower and the Hancock Center. Do you want an even better view? Because there is one way to get it… There is a HUGE Ferris wheel that you can ride to get a stupendous view of the entire Chicago skyline and Lake Michigan!

Visit Buckingham Fountain in Grant Park.

After exploring Navy Pier, head to Grant Park, another of Chicago’s excellent downtown parks. Here you’ll have the chance to explore a huge area of green space, complete with monuments, statues, and a great lakeside walkway. At the heart of Grant Park, you’ll see Chicago’s most famous and beautiful fountain: Buckingham Fountain

Buckingham Fountain is at the center of Grant Park and is a great place to sit and enjoy a coffee or picnic. The fountain itself is beautiful, but it is made even better by the great Chicago skyline in front of you, and Lake Michigan behind.

Further South in Grant Park you’ll find three other excellent Chicago sightseeing spots to consider adding to your 3 day Chicago itinerary:

Field Museum, Shedd Aquarium + Adler Planetarium

On the south side of Grant Park are 3 beautiful buildings, each of which houses an awesome adventure. The Field Museum is one of the largest natural history museums in the world and is home to some of the best exhibits you can possibly imagine. When we visited in the past, the dinosaur exhibit left us astounded, as they had a full-size Tyrannosaurus Rex named Sue!

The Shedd Aquarium is a world-class aquarium located just east of the Field Museum on Lake Michigan. This aquarium is stunning both from the outside and inside and offers hours of exploration as you make your way through the grounds.

Finally, the Adler Planetarium, America’s FIRST planetarium, is a wonderful place. This place offers the chance to explore things that are out of this world, literally. If you are at all interested in space, astronomy, or astrophysics, then you will have the time of your life at the Adler Planetarium.

Finish your long weekend in Chicago at River North.

River North is the area just north of the Chicago River. Whoever named it wasn’t very creative, but they were very accurate.

River North is absolutely FULL of awesome bar and restaurant destinations. As with many neighborhoods in Chicago, the best way to experience it is by hopping from place to place. When you find a place you love, stay as long as you’d like, then move along to the next place! That is the Chicago way of experiencing the nightlife.

Chicago is an enormous place, sprawling for miles and miles. The downtown area has many neighborhoods, each of which has pros and cons for visitors to the Windy City.

The best places to stay for 3 days in Chicago are near the Chicago River, specifically River North, Gold Coast, Streeterville, and The Loop.

In addition to those, a few more great neighborhoods are Lakeview, Lincoln Park, West Loop (which is home to great Chicago street art ), Near North, and Old Town.

Here are a few great hotel recommendations for budget, mid-range, and luxury travelers.

Godfrey Hotel — The Godfrey Hotel is in the River North neighborhood, and is right in the middle of many of the best activities on your 3 day Chicago itinerary. On top of the great location, the hotel is beautiful on the inside and gets excellent reviews. The Godfrey Hotel is a wonderful place to hang your hat while exploring Chicago.

Check rates & book your stay at The Godfrey Hotel today!

Hyatt Regency Chicago — The Hyatt Regency Chicago is located in The Loop neighborhood, right on the Chicago River.

Many of the rooms in the Hyatt Regency have beautiful views of the Chicago River, the skyline, and the city streets.

The rooms are wonderful, the price is good, and the location is excellent. Additionally, the fitness center, meeting rooms, an on-site bar and restaurant, and access to Chicago activities make the Hyatt Regency one of the best places to stay in Chicago.

Check rates & book your stay at the Hyatt Regency Chicago today!

The Langham — Now, to the creme de la creme. If you’re a luxury traveler looking for the best hotel in Chicago, look no further than The Langham.

First off, the location could not be better. Located right on the Chicago River in River North, you’ll be within walking distance of nearly everything on your itinerary.

Additionally, The Langham pulls out all the stops when it comes to amenities. The on-site spa, fitness center, pool, and deluxe bar and restaurant are all five stars. Of course, the rooms are wonderful as well, and nearly all have stunning views of the cityscape.

Check rates & book your stay at The Langham today!

Chicago and food go hand in hand. You could explore a new food destination in Chicago every night for the rest of your life, and not eat at the same place twice. Not going to fact check that, but it is probably true. There are awesome restaurants on every corner, all across the city!

Here are four must-visit restaurants in Chicago that we love. 

Chicago-Style Pizza – Giordano’s

You can’t come to Chicago and not try some Chicago-style pizza. You literally can’t, it is impossible. The best Chicago-style pizza is at Giordano’s. The pizza here is absolutely LOADED with cheese and toppings, more than you have ever had, guaranteed. One slice and you’ll be satisfied, two slices and you’ll be stuffed. Be prepared to have leftovers!

Portillo’s is a Chicago institution. This started as The Dog House, a hot dog stand, and grew into Portillo’s, a delicious restaurant serving beef, burgers, and Chicago-style hot dogs all across the city. Portillo’s is yummy, quick, and is a Chicago must. Try the chocolate cake shake, you’ll be glad you did.

Happy Camper

Happy Camper is an excellent classic pizza place located in the Near North neighborhood, which offers an excellent atmosphere. This is a great place to watch sports, meet friends, enjoy a happy hour, and of course, try some pizza!

The toppings are creative at Happy Camper, and the pizza is DELICIOUS. There is also a huge selection of local and imported beers to try.

Girl and the Goat

Girl and the Goat is an absolutely EXCELLENT restaurant located in the West Loop neighborhood on Randolph Street. T he food here is delicious and is very creatively and expertly prepared.

Call ahead for a reservation at Girl and the Goat, as there may be a long wait if you just show up asking for a table. If you do just show up, however, this is worth the wait.

And you can walk across the street to one of the many bars on Randolph while you wait for a table at Girl and the Goat!

Bonus: take a Chicago food tour!

In a city as centered around food as Chicago, taking a food tour is one of the best ways to explore the city’s cuisine. 

Not only will you be able to sample a wide variety of classic dishes without committing to a whole portion, you’ll also learn plenty about Chicago’s history and culture along the way!

This popular food tour gets rave reviews and is an excellent addition to your long weekend in Chicago.

Book your food tour in Chicago today!

Getting around for 3 days in Chicago is in most ways easy, but can sometimes be challenging.

The public transport system is the easiest and most inexpensive way to get around, followed by cabs/Uber/Lyft, and finally driving yourself.

Much of the 3 days in Chicago itinerary laid out above, however, can all be completed by exploring on foot, especially from the recommended hotels. The awesome destinations and great parks are relatively close together and can be reached with a nice walk in the Chicago air.

Chicago has one of the best public transport systems in the US. The elevated train, AKA the ‘L’, brings people across Chicago east, west, north, and south. The ‘L’ stops at all of the amazing sites in the city, as well as O’Hare Airport, Midway Airport, and all the major thoroughfares.

If you would rather avoid public transportation, then the best way to travel around during this 3 day Chicago itinerary is with a cab/Uber/Lyft. Traveling this way is likely the fastest if you can avoid rush hour, and the most convenient. However, it will be more expensive than using the ‘L’ trains.

Finally, you, of course, have the option of driving yourself around town. In our opinion, this is the most stressful way to get around, as you’ll have to worry about parking in the busy downtown streets. This is a challenge and is made worse considering that many hotels offer parking fees.

The best time to plan a long weekend in Chicago is during the summer. The weather during the summer is absolutely perfect, and it’s definitely the easiest time to pack light for a Chicago vacation (if you visit during the blustery winter, be sure to carefully consider what to wear in Chicago !). This is also the best time to explore the awesome parks, beaches, and outdoor destinations in the Windy City.

Each year in the summer, Lollapalooza brings huge crowds looking for an awesome time and great music. Lollapalooza draws many of the best music acts in the world, so traveling to Chicago during the music festival is a great opportunity. On top of this festival, many great music artists perform regularly at Wrigley Field, Soldier Field, the United Center, and the other great venues across Chicago.

Coming in a close second to the Chicago summer is the spring when the city defrosts after its long Chicago winter and comes alive. There is nothing quite like spending 3 days in Chicago when the atmosphere is on the rise, as it is in spring.

Also during this time is St. Patrick’s Day, one of the largest holidays in Chicago. On St. Patrick’s Day the river is dyed bright green, and the partygoers are out in force.

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4 thoughts on “3 Days in Chicago: The Ultimate Weekend in Chicago Itinerary”

I’d like to follow for future information

Thanks for this comprehensive guide! It made planning a trip to Chicago so much easier!

As a frequent traveler to Chicago, who lives just a few hours away, I want to mention a few places that truly make Chicago iconic. The Palmer House Hotel is the best in the City. Right outside the doors of the Palmer House is a Chicago favorite, with a long history, called Miller’s Pub. Grab an Allagash White beer on tap – a local favorite. Don’t miss a food tour of Chinatown. There is so much history there, and the food is really amazing! Other amazing foodie spots in Chicago are Bongo Room for brunch and Cafe Babareba for Spanish style tapas (do not miss the baked goat cheese in tomato sauce). An architectural tour on the Chicago River is a lovely way to spend the day and if that isn’t your thing, the water taxis are a fun way to get around.

Agrred with the other poster–This itinerary is hugely missing the architecture tours! Best thing to do in the city. River north is fine, but kind bro-y for lack of a better descriptor. Bongo room is in Wicker Park which I describe as our Williamsburg. Not quite as artsy and cool as it was 5 years ago but still very fun!

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One-Day Itinerary

One Day in Chicago: The Perfect Itinerary

TripSavvy / Cory Giguere 

Don’t let the winds blowing off Lake Michigan scare you— Chicago , the Windy City, is a metropolis full of culture and history. Sightseers flock to the birthplace of the skyscraper, for its: Michelin-starred restaurants ; major league sports teams; world-class theater, dance, music, and film; festivals; 26 miles of lakefront; well-curated museums ; and stellar shopping. Chicago is also full of green spaces that are worth exploring like Chicago Botanic Garden and The Morton Arboretum . No matter what you do, or where you go, you’ll appreciate the city’s midwestern allure, with a bit of urban edginess. 

This walking-city, with 2.7 million residents, utilizes speedy public transportation to get from point A to point B. As you get on and off the elevated rail, or L, you’ll notice a mashup of sleek and modern buildings with loads of history and nods to the past throughout Chicago’s 46 historic districts and 77 vibrant neighborhoods. Chicago River architecture tours or walking excursions will highlight the City of the Big Shoulders’ storied past—the rise of a transportation hub, the Great Chicago Fire, the World’s Columbian Exposition of 1893, prohibition era, and Chicago’s public enemy number one, Al Capone .

Whether you’re a first-time visitor to the Second City, or a seasoned local, peruse this 24-hour itinerary for an across-the-board exploration of what Chicago has to offer, highlighting must-see tourist spots as well as local neighborhood gems.

The Night Before

Night: Arrive in Chicago and check-in to your accommodations—there are 119 hotels to choose from in the central business district. Luxurious options in the city include: Waldorf Astoria Chicago , Four Seasons Hotel Chicago (the spa here is fantastic), The Langham Chicago , Park Hyatt Hotel Chicago , and The Peninsula Chicago (the lobby is exquisite). Other well-located alternatives are Hotel Zachary , near Wrigley Field (the second oldest ballpark in Major League Baseball); Hotel EMC2 , with a robot concierge; and InterContinental Chicago Magnificent Mile , with a hidden hole in the wall for a prohibition-era alcohol stash.

Intrepid families that would love to spend a night at one of the museums can bring a sleeping bag and a sense of adventure to Adler Planetarium’s Astro Overnights, the Field Museum’s Dozin’ with the Dinos, Overnights at the Shedd Aquarium , or the Museum of Science and Industry’s Science Snoozeum.

7:30 a.m.: Take advantage of waking up in one of the best cities in the world and go for a leisurely jog or a fast-paced walk along the Chicago Riverwalk, a 1.25-mile stretch that has Adirondack chairs toward the east end for catching your breath. You’ll pass by stunning architecture, art installations, and boats cruising up and down the Chicago River. Continue on to the paved Chicago Lakefront Trail, along Lake Michigan, which runs from Ardmore Street on the north side to 71st Street on the south side, traversing many historic neighborhoods like Lincoln Park, South Loop, Bronzeville, and Hyde Park. The skyline views, when you’re facing south, are incredible, especially at this time of day. You can see Navy Pier , Chicago’s most-visited attraction, from the trail, with its Centennial Wheel rising high in the sky. For great people watching, linger at Oak Street Beach for a beat. (The 606, in Logan Square, is another great place to run that is popular with locals. This neighborhood park was created on the old elevated Bloomingdale train line—similar to New York’s High Line .)

10 a.m.: Make your way to Cindy’s for brunch, located on the rooftop of the famed Chicago Athletic Association Hotel , formerly a men-only social club. You won’t believe the terrace view of Millennium Park, The Art Institute of Chicago (the “Historic Route 66” begins in front of the Art Institute), Lake Michigan, and the shops and restaurants below at street level. Make reservations well in advance—this place is always packed—and order the avocado toast and the roasted vegetable strata. Save room for the house-made vanilla mascarpone Danish, with roasted cherries.

Noon: Across from Cindy’s is the 24.5-acre Millennium Park , a well-loved public space that is home to the Jay Pritzker Pavilion, Cloud Gate—the Instagram-worthy shiny bean-shaped sculpture, Crown Fountain, and Lurie Garden. Millennium Park Campus is also where you’ll find Maggie Daley Park, the best place to go if you have kids in tow.

1:00 p.m.: Meet up with Chicago Architecture Foundation ’s guide to learn about Chicago architecture and history on a two-hour walking tour through the city. You’ll get the lay of the land and learn more than you dreamed possible to enrich your time spent in the city. On the way, caffeinate with a cold brew or bulletproof coffee at Goddess and the Baker , located at Wacker Drive and Lasalle Street.

3:00 p.m.: You can’t leave Chicago without weighing in on which pizzeria serves up the best slice of deep dish . Is it Giordano’s, Lou Malnati’s, Pizzeria Due, Gino’s East, Piece, or Home Run Inn? You decide.

5:00 p.m.: Walk off that heavy pizza and stroll along the Magnificent Mile , a 14-block stretch of Michigan Avenue—from the Chicago River to Oak Street—that is mecca for shopping. Here, you’ll find malls and boutiques full of designer threads as well as affordable clothing brands. Keep in mind, this area is usually congested with shoppers, especially around the holidays and on weekends, so it’s best to plan out which shops you’d like to see in advance. Take a few snaps in front of the famous Chicago Water Tower , built in 1869, on the north end of Michigan Avenue. If shopping isn’t your thing, why not take an Intro to Climbing class at Chicago’s Brooklyn Boulders , located in Greek Town, west of the river, near Ogilvie Transportation Center?

6:00 p.m.: Take the high-speed elevator up to the observatory at 360 Chicago (formerly The Hancock Observatory) where, on a clear day, you can see Michigan, Indiana, and Wisconsin. Test your fear of heights on the Skydeck open-air viewing deck and see Michigan Avenue, 1,000-feet below, in the TILT attraction.

7:00 p.m.: You’ll want to experience Chicago’s diverse theater, music, or dance scene—the city has more than 250 theaters, 225 music venues, and 200 dance companies. Long-standing theaters include: The Second City in Old Town, Goodman Theatre and Chicago Theatre in the Loop, Music Box Theatre in Lakeview, Blue Man Group at Briar Street Theatre in Boystown, Steppenwolf Theatre Company , Chicago Shakespeare Theater , Lookingglass Theatre Company , just to name a few. And, of course, Chicago has no shortage of great live music, especially blues and jazz music (the term “jazz” was coined in Chicago). Music festivals like Chicago Blues Festival, Chicago Jazz Festival , Lollapalooza , Pitchfork Music Festival and Riot Fest are well-attended and loved in this city. Not to be missed is Chicago Symphony Orchestra , Lyric Opera and the Joffrey Ballet . The Harris Theater for Music and Dance is home to major Chicago dance troupes. You can’t do it all of course, so pick wisely and plan on returning to Chicago for another go-round in the future.

10:00 p.m.: For late-night noshes, local beers, and inventive cocktails, pop over to Lincoln Park’s Broken Barrel Bar , with Chef Bryant Anderson at the helm. This place is great for that non-touristy neighborhood feel that Chicago is really known for and you’ll get a sense of what one Chicago community is like by playing a game of bags or hanging around in the beer garden. Other great options, with completely different environments are: The Berkshire Room in River North, Milk Room in the Loop, The Aviary in the West Loop , The Violet Hour in Wicker Park, River Roast on the Chicago River, and The Optima in Old Town.

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Table of Contents

How to Plan Your Chicago Trip

Planning a trip to Chicago is very easy if you plan it properly. At the same time, planning your Chicago trip can be hard without knowing the starting point.

Nothing to worry, this post will help you plan a trip to Chicago that fits your budget and preferences. On this page, you would find all necessary information and links to my guide that will help you plan a trip to Chicago.

Being one of the major cities in United States of America, it is very easy to get to Chicago by air. Chicago city has two major airports – O’Hare International and Midway airport.

You can also get to Chicago by train or by bus, but I recommend you to go by air to save time. If you live in neighboring states then I recommend you to drive your car over flights, unless you find a cheap airfare to Chicago.

For booking a flight to Chicago, I recommend well-known companies such as Travelocity , Priceline or Expedia . Make sure to check their Chicago vacation package deals to save even more when you book Flight + Hotel together.

I recommend Expedia.com for booking a Chicago hotel for less. Try to book flight and hotel together to save more money.

Book Chicago Hotels for Less

Also, when planning your trip to Chicago, you must book your hotel as early as possible. Especially if you are traveling during peak season – June, July and August months. If you find any good hotel room deals then it is very likely to get sold out quickly.

If you find a good hotel deal during peak season then I recommend you to book hotel room immediately. You can read my where to stay in Chicago post to get more idea while booking a hotel room.

You can check hotel deals on Booking.com , Expedia.com or Hotels.com to get the best rates.

I recommend you to adjust your travel dates to avoid any major conventions in Chicago. Try to avoid major conventions to get lower rates on hotels as hotel room rates will be very high.

It is always a good idea to catch one of shows or concerts in Chicago during your visit. You must book your show tickets online before you arrive in Chicago.

I recommend you to check out Ticketmaster or theater website to book show tickets online.

You can read my When to Go to Chicago post to get more information about best time to visit Chicago.

You must check weather before packing your bags for your trip to Chicago. Weather in Chicago is very unpredictable so it is always good to check weather a day before your travel dates before packing your bags.

International Travelers require USA visa to visit Chicago. If your country of citizenship falls under the Visa Waiver Program (VWP), then you can enter the United States without a visa that will allow you to stay for 3 months.

Whether you are US Citizen or International visitor, you may bring in pre-defined size of alcohol and tobacco products. You are allowed to bring in cigarettes and cigars, but there are some restriction on cigars from Cuba. You can get detailed information on US custom website.

I recommend you to utilize public transportation in Chicago to save time and money. Both O’Hare and Midway airports are connected with downtown through EL trains. O’Hare is on Blue line El trains and Midway is on Orange Line El trains. You may like my post on getting around in Chicago .

If you are planning to travel through trains and buses then I recommend you to purchase CTA Visitor Pass. It allows you to take unlimited train and bus rides for a 24-hour period. It will save your lot of money.

CTA Visitor Passes are sold at airports, transportation hubs or tourism information center. You can also purchase them in advance online at transitchicago.com .

Chicago city has total seven different EL train lines, out of all you will probably need “The Red Line” in downtown Chicago as it runs parallel to the Michigan lake, along several top Chicago attractions.

I also recommend tourists to take Brown Line which runs around the downtown Chicago loop.

I highly recommend you to take at least one EL train ride to get the different experience in Chicago, passing through downtown buildings and residential areas.

Senior traveler above 60 years of age can get discounted rates on admission to participating hotels, attractions and theaters. Also senior residents of Chicago can travel for free on local public transportation with valid proof.

Chicago Trip Planner Guide

• When to Go to Chicago – Advice on best time to visit Chicago.
• Getting to Chicago – Advice on getting to Chicago
• Getting Around Chicago – How to get around Chicago for tourists
• Airport Transportation – Best way to/from Chicago airports.
• Weather in Chicago – What is weather like in Chicago?
• What to Pack for Chicago Trip – Packing tips for Chicago trip.
• Traveler’s Helpline – Ask and give advice to fellow Chicago travelers.

Where to Stay in Chicago

Where should you stay in Chicago? It’s challenging and more confusing while planning a Chicago trip or even for a local getaway to unwind and relax in hotel away from daily routine life. Chicago is one of the largest metro city in USA. Chicago city covers large radius of area, that offers plenty of hotel rooms to stay, and more options creates more confusions.

If you are not familiar with Chicago then it might get pretty confusing when it comes to booking a hotel room to stay during your trip. You can find more information before booking a hotel room in my where to stay in Chicago post.

• Where to Stay – My recommendations on booking a hotel room in Chicago!
• Chicago Downtown Hotels – Get deals on downtown hotels.
• Chicago Pet-friendly Hotels – Check out pet-friendly hotels in Chicago before you plan your trip with your furry friend.
• Chicago Luxurious Hotels – Plan a luxurious getaway in Chicago.
• Chicago 5-Star Hotels – List of 5-star hotels in Chicago.
• Chicago 4-Star Hotels – List of 4-star hotels in Chicago. Most likely you will be booking one of these hotels.
• Chicago 3-Star Hotels – List of budget-friendly hotels in Chicago.
• Chicago Hostels – Get advice on hostels in Chicago.
• How to Compare Chicago Hotels
• How to Find a Hotel Room in Chicago

What to Do in Chicago

There are plenty of things to see and do in Chicago. Most of all top attractions are located in and around the downtown Chicago, including Willis Tower, Navy Pier, the Field Museum of Natural History, the Shedd Aquarium , the Millennium Park and Magnificent Mile.

I highly recommend you to use one of the Chicago attraction passes to save money on admission to attractions. I would suggest you to use either Go Chicago Card or Chicago CityPass based on your number of days on hand to explore the windy city.

• Family Friendly – Best family friendly Chicago attractions.
• Kids Friendly Chicago – List of kids friendly Chicago attractions.
• Chicago Museums – Plan which museum fits your taste.
• Zoos & Aquariums – List of zoos and aquariums in Chicago.
• Chicago Shows – Famous Chicago shows and more

Chicago Tours

Chicago city offers many tours such as Chicago food tours, boat tours on lake and Chicago river, bus tours, walking tours, Segway tours and many more. I recommend you to book tour tickets online at Viator.com in advance before visiting Chicago.

If you are planning to buy Go Chicago Card to explore Chicago then check before purchasing tour tickets separately as some of these tours are already included in all-inclusive Go Chicago card.

• Chicago Boat Tours – Ways to sail on Chicago river and Michigan lake.
• Chicago Bus Tours – Go see Chicago with your guides on wheels.
• Chicago Food Tours – Eat and have fun in Chicago.
• Chicago Segway Tours – See Chicago without walking.
• Chicago Day Cruises – Sail Michigan Lake to enjoy excellent skyline views.
• Chicago Night Cruises – Great way to enjoy Chicago Skyline at night time.

Chicago Itineraries

I have come up with some sample Chicago Itineraries that may help you plan your visit to Chicago. I would recommend you to create your Chicago Itinerary using popular Chicago attraction passes, Go Chicago Card or Chicago CityPass , to save lot of money on admission tickets to attractions.

• One Day Chicago Itinerary – Explore Top Attractions on Budget with Go Chicago Card
• Chicago 1-Day Itinerary – Plan a trip to Chicago with sample one day itinerary for Chicago.
• Chicago 2-Days Itinerary – Plan a trip to Chicago with sample second day itinerary for Chicago.
• Chicago 3-Days Itinerary – Plan a trip to Chicago with sample third day itinerary for Chicago.
• Chicago 4-Days Itinerary – Plan a trip to Chicago with sample fourth day itinerary for Chicago.

Plan a Trip to Chicago with Maps

• CTA – CTA Bus and Rail lines, as well as connecting services in Chicago
• Metra – Travel to Chicago suburbs.
• Bike – Plan your bike path before you start.

Where to Eat in Chicago

• Best Chicago Restaurants – List of top Chicago restaurants that fits your taste buds.
• Best Waterfront Bars – Advice to enjoy the waterfront bars in Chicago.

How to Book Chicago Trip

• Find Chicago Vacation Packages – Book Flight + Hotel together and save up to $525 per person.
• Find Chicago Hotel Rooms
• Find Flights to Chicago
• Car Rentals in Chicago
• Go Chicago Card – Save 55% on admission to Chicago attractions.
• Chicago CityPass – Save 50% on VIP admission to the 5 best attractions in Chicago.
• Book Chicago Activities – If Chicago attraction passes are too much for you then book specific activity in Chicago.

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Save up to 45% with go chicago card.

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Help me out! When visiting local businesses or attractions, be sure to say you found them on Go Visit Chicago!

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The Ultimate Chicago Family Vacation | 3 Days in Chicago With Kids

This post may contain affiliate links, view our disclosure policy .

Look no further for the ultimate Chicago family vacation itinerary perfect for spending 3 days in Chicago with kids!

The magnificent city of Chicago receives recognition as being the ‘Best Big City in the U.S.’, as well as being the ‘#1 World’s Best City for Having it All’ .

In this post, you’ll learn about what to see and do, how to get around, and how to plan a 3 day Chicago itinerary when visiting Chicago with kids.

In addition, our Chicago family vacation itinerary will guide you to the most popular things to do in Chicago while helping you plan the best visit ever!

The links on this page are Amazon affiliate links. If you click on the links and make a purchase, I receive a small commission at no extra cost to you.

Table of Contents

Chicago Family Vacation

If you’re wondering, “Is Chicago a good family vacation spot?”, I would overwhelmingly say, “Yes!”.

In fact, if you’re familiar with popular urban vacation destinations, it’s more than likely that Chicago is on your  US bucket list !

Located on the shore of Lake Michigan in Midwest USA, Chicago, Illinois is a glorious city with a population of 3 million people.

Chicago is a tourist’s dream as it has a magnificent, walkable downtown area filled with gorgeous parks and sculptures, impressive museums, several  famous Chicago foods , and beautiful lakeside views.

Perfectly blending the hustle and bustle of city life with a degree of friendliness that you’d expect from a small town, this diverse area is a must-visit metropolitan wonder.

Whether you’ve dreamed of walking through Millennium Park and photographing “The Bean” or you want to enlighten your kids by checking out the ever-popular Adler Planetarium, there are so many family-friendly Chicago attractions!

Oh, and psst…we LOVE Chicago so much, that we’ve written several other guides to help you plan your trip!

• What to Wear in Chicago: A Visitor’s Guide for Every Season!
• What to do in Chicago in Winter (+ 3-Day Itinerary)
• Top 5 Kid-Friendly Restaurants in Downtown Chicago
• 25 Things to do in Chicago at Night
• A Complete List of Things to do at Navy Pier Chicago
• Famous Chicago Food: 5 Iconic Chicago Foods to Try!

Best Time to Plan A Chicago Vacation

The best time for a Chicago family vacation is during the months of May, June, September, and October.

In other words, plan a family trip to Chicago when the weather is mild during the late spring, early summer, and early fall.

In addition, be sure to consider what to wear in Chicago depending on when you visit, as the weather varies drastically.

Though Chicago in summer can be hot and humid, many are drawn to the area during this time in order to take advantage of its lake activities and outdoor events.

Keep in mind, however, that Chicago gets very busy with tourists over the weekends and holidays.

We just so happened to visit Chicago in September over Labor Day weekend.

Though the sidewalks throughout the city were very crowded, the holiday weekend special events still made this a great time to visit.

Additional planning tip: If you’re not afraid to get bundled up and brave the cold, we’ve found that visiting Chicago in winter can be just as fun!

Read here to learn about our winter getaway in Chicago which includes the best things to do in Chicago in winter .

Chicago Family Vacation Itinerary: Day 1

The following breakdown of several family activities in Chicago can be applied to a two-day itinerary for Chicago, or extended to a 4-day Chicago itinerary.

Either way, here are our favorite Chicago vacation ideas that we’ve done time and time again.

• Arrive in Chicago and admire the beautiful Chicago skyline
• Check-in to your hotel
• Have dinner at the iconic Portillo’s Hot Dogs

Arrive In Chicago

Day 1 of our 3-day Chicago family itinerary involved a 6-hour drive from our hometown (We love road trips!)

We found travel down Interstate 90 and into the heart of downtown Chicago to be an absolute breeze, with the exception of heavy traffic at times.

Considering driving to the Windy City too?

We have compiled essential tips on how to master a family road trip , and how to create “Are We There Yet” goodie bags to help make it the best road trip ever!

Check-In To Your Hotel

For this Chicago family vacation, we stayed at the Best Western River North .

Best Western River North is centrally located to several downtown Chicago points of interest.

It is also really close to some great places to eat with kids, such as the SafeHouse, Portillo’s, McDonald’s, and Hard Rock Cafe.

Also adjacent to Best Western River North is a BP gas station and Walgreen’s pharmacy and convenience store.

Check-in was quick and efficient and the front desk staff was very friendly.

They even offer free ice cream sandwiches and sherbet push-ups around the clock!

Like most hotels downtown, there is a daily fee to park on-site. The lot is staffed by a parking attendant and is safe and secure.

Our room was comfortable and stylish; just large enough for 2 double beds and an additional cot. The hotel itself has a heated indoor swimming pool on the top floor.

Next to the pool is an outdoor rooftop deck with comfortable lounging chairs and amazing views of the city.

We loved taking a glass of wine up to the deck each night to relax while the kids swam. The presence of the rooftop deck was definitely the best selling point for us.

Breakfast is not included at Best Western River North, but for a small cost, you can visit the onsite restaurant for made-to-order breakfast items.

Portillo’s

No family trip to Chicago is complete without experiencing the 5 famous Chicago foods that are the cornerstone to every visit.

Being right across the street from our hotel, Portillo’s was an easy choice to start off our epic Chicago food experience.

What started as a hot dog cart, Portillo’s restaurant serves up Chicago-style hot dogs, Italian beef sandwiches, burgers, salads, and other sides.

Their casual atmosphere, amazing food, and welcoming ambiance make this one of our most recommended kid-friendly restaurants in downtown Chicago .

Additional planning tip: If you’re looking for a complete foodie experience, schedule a Chicago Food Planet walking food tour that covers the Chicago hot spots.

Chicago Family Vacation Itinerary: Day 2

• Walk and shop on Magnificent Mile
• Take an Architectural River Cruise
• Have lunch at Wildberry Pancakes and Cafe
• Tour and take photos in Millennium Park
• Spend time enjoying Navy Pier

Magnificent Mile

Start off your Chicago family trip by grabbing a cup of coffee and taking a leisurely walk along Chicago’s Magnificent Mile .

Magnificent Mile is the nickname of the long stretch of upscale shops and restaurants located along Michigan Avenue.

It is also home to the world-famous John Hancock building (home to 360 Chicago and TILT) and the historic water tower and pumping station that were two of the only structures to survive the Chicago Fire of 1871.

Walking along the bustling sidewalks of the Magnificent Mile is not to be missed in your Chicago 3 day itinerary.

Kid-friendly stops include the Disney Store, American Girl Place, Chicago-famous Garrett P opcorn , and Dylan’s Candy Bar.

Chicago 3 day itinerary planning tips: Depart your hotel at 9:30 AM on foot.

Plan to spend 20 minutes walking the entire Magnificent Mile from north to south, with additional time allotted for your choice of shopping and stops.

View this post on Instagram Our experience on Chicago Architecture Center’s River Cruise aboard Chicago’s First Lady was nostalgic, informative, relaxing, and overall AMAZING! So thankful for this opportunity! #choosechicago #cruisechi2019 #cruisechicago #cafcrivercruise #travelwithaplan #TWAP #familytravel #chicagowithkids A post shared by Jennifer Brommer (@travelwithaplan.jen) on Aug 31, 2019 at 5:50pm PDT

Architectural River Cruise

If you’re looking to plan a family vacation in Chicago, IL, our top recommendation is to get tickets to go on a Chicago architecture river cruise (if the weather and season permit).

After walking down Magnificent Mile to the south, you will come across the Michigan Avenue Bridge and Chicago’s Riverwalk.

Here is where you access the Chicago Architecture Foundation Center River Cruise aboard Chicago’s First Lady .

For GPS directions, use 112 E. Wacker Drive and look for their blue awning marking the stairway down the river walk dock.

Though there are a few other river cruise options, we absolutely loved our experience on the CAFC River Cruise and highly recommend it.

The boat was family-friendly, fun, and nostalgic, and the commentating was highly informative.

There is a full bar aboard that includes snacks, drinks, and cocktails.

Imagine a glorious float down the Chicago River learning about the towering skyscrapers – while sipping a Mimosa with Tony Bennett music playing in the background.

Chicago family vacation planning tips: Secure 10:30 AM CAFC River Cruise reservations .

Pick up your tickets at 10:00 AM and get in line no later than 10:15 AM to be the first to board the First Lady.

Seats are not pre-assigned and are first-come-first-serve.

Choose seats on the upper deck along the sides for the best-unobstructed photo ops.

The entire river cruise lasts 90 minutes.

Millennium Park

No vacation in Chicago would be complete without visiting Millennium Park! In addition, if you’re planning a family trip to Chicago on a budget, it’s nice to know that all of the attractions in Millennium Park are free!

After stopping for lunch at Wildberry Pancakes and Cafe , spend plenty of time visiting Chicago’s iconic Millennium Park .

Here is where you will find the most talked-about (free) attractions that people typically refer to when visiting Chicago.

Each of these attractions should be part of any Chicago trip with the family!

The most popular attraction in Millennium Park is the Cloud Gate sculpture.

Commonly referred to as ‘The Bean’, Cloud Gate is an art piece that is a great place to take Instagram photos and selfies, especially off of its reflective surface.

You can see the reflection of the Chicago skyline, walk under The Bean, and take photos from all sides.

Despite the crowds, the space is large enough to accommodate large amounts of visitors.

(It is highly unlikely to get a photo without other tourists in it, however.)

Crown Fountain

Another highlight of Millennium Park is Crown Fountain .

Here, two huge 50ft LED screens light up while displaying the faces of average Chicago residents.

Every 5 minutes, the mouths of the faces spill water onto the ground creating a shallow reflective pool.

The fountains make a great place for kids to cool off in the hot summer months.

BP Pedestrian Bridge

The gigantic stainless steel BP Bridge connects Millennium Park to Maggie Daley Park.

Though there are other outlying sidewalks to get to Maggie Daley Park, make it a point to walk across this unique pedestrian bridge.

Its shiny silver surface, snake-like curvature, and prize-winning architecture make it an experience to remember.

Maggie Daley Park

As one of the most kid-friendly Chicago activities, be sure to visit Maggie Daley Park!

After crossing BP Pedestrian Bridge you will enter Maggie Daley Park .

Here you will find mini-golf, a climbing wall, and 5 playgrounds themed for different ages and abilities.

Large tube slides for older kids, innovative swings, and a splash fountain for younger ones are a few other highlights.

The rolling hills and valleys of rubber turf, as well as perfectly incorporated green space, make this a dynamic area that will keep kids entertained for hours.

For those families with small children or kids of all ages for that matter, Maggie Daley Park is a must-do during your Chicago itinerary.

Lakefront Trail

Upon exiting Maggie Daley Park and heading towards the water you will come across an entrance onto Chicago’s Lakefront Trail .

Chicago’s scenic Lakefront Trail is an 18-mile paved trail that follows along the shoreline of Lake Michigan.

With separate lanes for walking, running, and biking, head north on this trail from the Millennium Park area to get to Chicago’s Navy Pier.

The 15-minute walk along Lakefront Trail will allow you to admire Lake Michigan and watch the on-water boats, kayaks, and wildlife.

Chicago family vacation planning tip: Plan to spend 1-2 hours visiting Millennium and Maggie Daley Park.

You may need more time if you have smaller children who want to spend more time at the park.

When considering what to do in Chicago in 3 days, no family itinerary is complete without a visit to the historic Navy Pier .

Over the past few years, Navy Pier has become one of the most popular things to do in Chicago as well as is one of the best Illinois attractions for families.

Likewise, there are literally so many things to do at Navy Pier Chicago with kids!

Ride the 200ft tall iconic Centennial ( Ferris ) Wheel and other outdoor amusement rides, or dine at one of its many restaurants.

Other activities at Navy Pier include the Amazing Chicago Funhouse Maze, Virtual Rush: Chicago virtual reality experience, and Lake Michigan sightseeing cruises.

Additional planning tip: If you’re looking for things to do in Chicago at night , save riding the Centennial Wheel for when the sun goes down!

Riding the Centennial Wheel at night is super fun and provides amazing views of Chicago’s lit-up skyscrapers!

View this post on Instagram One of the biggest highlights of our recent trip to Chicago was the #Chicagofoodplanet Signature Food Tour @ Navy Pier! Our amazing host Faith treated us to Navy Pier’s finest eats without having to wait in lines, and while humor and hospitality! A-MAZING! #chifoodplanet #chifoodplanettours #chicagofood #navypierfoodtour #navypier #chicagowithkids #foodplanet #travelwithaplan #TWAP #familytravel #bestplacestogo A post shared by Jennifer Brommer (@travelwithaplan.jen) on Sep 4, 2019 at 10:21am PDT

*Click here for our exclusive FREE Family Vacation Packing List that is both customizable and printable!

Chicago Family Vacation Itinerary: Day 3

• Visit 360 Chicago and ride TILT
• Take a Chicago Big Bus tour
• Have lunch at Giordano’s Pizza
• Tour the Art Institute of Chicago
• Attend a Blue Man Group Chicago show
• Have dinner at SafeHouse Chicago

360 Chicago Observation Deck + TILT

Start off this morning of your Chicago 3 day itinerary by walking through the north end of Magnificent Mile via Michigan Avenue (to Water Tower Place).

Here you find the (former) John Hancock building, which is home to the 360 Chicago Observation Deck and TILT.

Located on the 94th floor, the 360 Chicago Observation Deck provides unparalleled views of Lake Michigan and the Chicago skyline.

[Included in the Chicago CityPass ]

It also offers interactive learning opportunities, a gift shop, and a modern bar and cafe.

For an additional cost, visitors of the Observation Deck can ride TILT.

TILT involves stepping onto a moving platform that slowly tilts you – in a standing position – outside the side of the building.

As you hold onto metal bars, the platform moves outward in 3 increments until you are angled in suspension over Michigan Avenue and the buildings below.

Chicago itinerary planning tip: We had 9:00 AM reservations for 360 Chicago. This is a very popular Chicago attraction so I recommend visiting in the morning as such when crowds are fewer.

Plan to spend 45 minutes to 1 hour here.

Chicago Big Bus Tour

If you’re planning a trip to Chicago, we highly recommend doing a hop-on-hop-off Big Bus Chicago tour as a way to learn and see more of the city.

Tickets for Big Bus Chicago can be purchased online or at any of the advertised Big Bus stops .

There are 2 Big Bus Chicago stops on the same block as the John Hancock Building, so this is where we boarded and began our hop-on hop-off experience.

Chicago itinerary planning tip: It is important to refer to the Big Bus Chicago route map to plan the places and timing of your stops.

The lower half of the bus provides covered seating, while the top half of the bus is open air.

Rain ponchos are provided free of charge in the case of rain.

Giordano’s Pizza

After boarding Big Bus Chicago at Stop #12, we rode continuously to Stop #4 at Millennium Park.

Here, we got off and headed for lunch at Giordano’s Pizza (130 E Randolph St, Chicago).

After having a slice of their famous deep-dish pizza while on the Navy Pier, we fell in love.

We couldn’t end our Chicago vacation without another round of this authentic Chicago-style pizza .

Additional planning tip: Plan to spend 1.5 hours at Giordano’s as the pizza alone take 45 minutes to bake.

Art Institute of Chicago

After lunch, we passed through Millennium Park to the adjacent Art Institute of Chicago .

One of the world’s greatest art museums, the Art Institute of Chicago goes out of its way to cater to families (+Kids under the age of 14 are free).

Our favorite family-friendly aspect was the Family Room.

Here, we got to create a customized family museum tour using the interactive Journey Maker.

Chicago itinerary planning tip: The Art Institute of Chicago is massive so plan to spend 60-90 minutes there, depending on the attention span of your kids.

Don’t forget to see Picasso’s, The Old Guitarist, and Grant Wood’s, American Gothic.

Blue Man Group Chicago

After finishing our tour of the Art Institute, we grabbed an Uber and headed to the Briar Street Theater.

Briar Street Theater is home to Blue Man Group Chicago , and is stop #5 of our Chicago 3-day itinerary!

Having heard so much about Blue Man Group , we were so excited about this unique experience.

In fact, as soon as we stepped into the bustling dark theater adorned with blue spotlights, we knew we were in for a treat.

A performance filled with music, art, obscurities, and crowd interaction, the Blue Man characters wow the crowd without ever speaking a word.

Never knowing what is going to happen next, the performance is highly engaging and keeps you at the edge of your seat.

This unforgettable experience is a must-see upon your next family trip to Chicago!

Chicago itinerary planning tip: We had 2:00 PM reservations for Blue Man Group Chicago.

The performance lasts 90 minutes with no intermission.

Uber drivers were readily available to take us back to the downtown Chicago area once the show was over.

Additional planning tip: If you’re looking for another Chicago activity that teens will love, check out Escape Game Chicago! Though we have not personally done one, the downtown Chicago location offers 5 different 60-minute escape rooms!

SafeHouse Chicago

(This location is temporarily closed due to the effects of the pandemic; check their website before visiting.)

After heading to the hotel to rest and get changed for dinner, we walked 5 minutes to our much-anticipated dining experience at SafeHouse Chicago !

Once arriving at the secret entrance, couples, families, and groups are welcomed in one-by-one and must give a password in order to be granted access to the restaurant.

If you do not know the password, silly actions must be performed in order to be let in while the rest of the visitors in the restaurant watch on.

Once inside, the dark, spy-themed decor and lighting are uniquely inviting.

Upon being seated, you are immediately given a name tag to identify your ‘agent name’. This is the name that the servers will refer to you as during your dining experience.

After ordering off the menu, children may participate in an interactive scavenger hunt or visit the in-house magician while waiting for their food.

Chicago itinerary planning tip: Due to its popularity and that it is one of the best Chicago restaurants with kids, reservations are highly recommended at SafeHouse Chicago.

Also, you should know that t he fun doesn’t end once your meal is complete. (There is a mysterious twist in getting out of the actual restaurant.)

Chicago CityPASS

There are literally so many things to do in Chicago that many people wonder about Chicago family vacation packages.

One of our best travel tips is that if you’re trying to see the best of Chicago in 3 days, the most affordable way to see the city is with the  Chicago CityPASS .

In fact, you can save 50% on visiting Chicago’s top 5 attractions with this one purchase alone.

Grab your CityPASS here  – you will not regret bundling your activities into this Chicago family vacation package.

Additional planning tip: Most of the museums have a separate entry and line for CityPASS holders which will also save you a great deal of time.

Chicago Family Vacation: Getting There

If you’re heading to Chicago with family, visitors typically travel there via plane, train, bus, or personal vehicle.

Chicago’s central location and the fact that it is accessible by many major interstates and highways make it easy to get there by car.

Be aware that there are several Illinois tollways as you drive into the city, so be sure to have spare dollar bills on hand.

If traveling from a farther distance, however, search for flights into either O’Hare International Airport or Chicago Midway International Airport.

How to Get Around Chicago

Chicago is a walkable city meaning that when staying downtown, the majority of the popular restaurants, sites, and attractions are all within walking distance to one another.

If staying downtown you simply do not need a car to get around once there.

For longer stretches, Uber vehicles are highly prevalent and can typically be found within 2 – 3 minutes of any given address.

In addition, Chicago is well-known for its convenient street system and its fantastic  public transit system .

Where to Stay in Chicago

If you’re planning a vacation in Chicago, IL, there are several options on  where to stay in Chicago .

Regardless, be sure to stay downtown so that you can do as little driving around as possible.

Choices downtown include staying within the Magnificent Mile, The Loop, or River North neighborhoods.

The Magnificent Mile is close to the John Hancock Building, Navy Pier, and upscale shopping.

The Loop is close to the Willis Tower and Millennium Park.

On the other hand, River North hotels are still within walking distance to major attractions but provide more budget-friendly options that often include pools and free breakfast.

Here are some of our favorite  Chicago resorts for families:

• Embassy Suites Chicago Downtown Magnificent Mile
• Embassy Sites Chicago Downtown
• Courtyard Chicago Downtonw/Magnificent Mile
• Homewood Suites Chicago Downtown/Magnificent Mile

Chicago Family Vacation: If You Have More Time

If you’re fortunate to be planning a Chicago 4-day itinerary, you’ll have time to do a few extra things.

The one area of downtown that we did not get to experience was the extremely popular Museum Campus which is home to several world-famous Chicago museums.

Places such as the Shedd Aquarium, the Field Museum of Natural History, and Alder Planetarium, are places that we will definitely visit during our next family vacation to Chicago.

The Museum of Science and Industry is another Chicago family favorite and should be considered if you like science and technology.

An important note is that both the Museum of Science and Industry and The Field Museum are both sensory-friendly Chicago activities for visitors with autism or sensory processing disorders.

[All Included in the Chicago CityPass ]

Thank you to Choose Chicago, Best Western River North, Chicago Architecture Foundation Center River Cruise aboard Chicago’s First Lady, Chicago Food Planet’s Signature Food Tour at Navy Pier, 360 Chicago and TILT, Art Institute of Chicago, Blue Man Group Chicago, and SafeHouse Chicago for hosting our family’s visits. I was not compensated for this Chicago 3 Day itinerary article. All opinions are my own. Jen

If you like our Family Chicago Vacation itinerary, here are our related posts to help plan your trip:

• 25 Exciting Things to do in Chicago at Night
• Famous Chicago Food: 5 Foods You Must Try During Your Visit
• Top 5 Kid-Friendly Downtown Chicago Restaurants that Your Family Will Love
• What to Wear in Chicago: A Visitor’s Guide For All Seasons
• Top 10 Things to do at Navy Pier Chicago with Kids
• Our United States Bucket List: 15 Exciting Places For Families to Go

*Before leaving, be sure to check our Travel Resources Page to find exclusive travel discounts and to book hotels, rental cars, and guided tours.*

Jen Brommer is a family travel expert. She has been featured as an authority on several notable travel websites and is a member of the Family Travel Association (FTA), Midwest Travel Network, and TravMedia global media network.

A prominent content creator and influencer on Instagram, Jen has over 150K unique monthly blog readers from countries all over the world. She has spent the last 16 years planning fun, and hassle-free family vacations for her family of 5.

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20 Comments

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This looks like such a fun trip to Chicago! We did the same river cruise pre-kid and loved it. Definitely planning a trip to Chicago with my son in the near future!

Awesome! We loved it there! Hopefully you and your son can do some of these same things 🙂

What a fun trip to Chicago! I’ve had quite a few dog-friendly Chicago trips and we always have a great time. The Architectural River Cruise is a must! It’s such a wonderful way to view the amazing buildings.

I noticed that it was very dog-friendly! We love that about Duluth, MN too!

I would love to visit Chicago!

Yes, it is truly great! Let me know if you ever need additional tips!

As a (former) Chicago resident, I can honestly say this is a great itinerary! Portillo’s Chopped Salad is my favorite and I grab one anytime I’m passing through Phoenix as they actually have a couple of Portillo’s locations.

That is the best feedback ever! Thanks for sharing! I didn’t have that salad…but will have to when we go back!

I would love the opportunity to do more of Chicago. Navy Pier was a big highlight but i’d love to do some of this other stuff!

Yes, there is literally so much to see and do for all ages! We will definitely be returning soon!

We adore Chicago – saving this four our next trip!

Yay! This itinerary was flawless for us! Let me know if you return!

Chicago is one of my favourite cities in the USA, this post has got me desperate to return!

Basking in the memories, it makes me want to return too!

My brother isn’t that far from Chicago! We should make a weekend of visiting him and seeing the city. Thanks for all the tips!

For sure! You’ll love it! Plus, you’ll get to see your brother!

Saving this! We have one day in Chicago on our upcoming October trip with kids and I can’t wait! Thanks for the tips!!

Yay! So glad that you find is useful! Have so much fun there!

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Plan a Trip

The RTA Trip Planner allows travelers to plan trips in the Chicago region using public transit (CTA, Metra and Pace) that include driving, biking and walking directions.

The following navigation utilizes arrow, enter, escape, and space bar key commands. Left and right arrows move through main tier links and expand / close menus in sub tiers. Up and Down arrows will open main tier menus and toggle through sub tier links. Enter and space open menus and escape closes them as well. Tab will move on to the next part of the site rather than go through menu items.

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Finding your way

We make it easy to find your way on transit.

Trip planning tools

The easiest way to plan a trip is to use a trip-planning service. Google Maps or the RTA Travel Information Center can all help you plan your trip.

Plan a trip with Google Maps

You can now get transit and walking directions from Google Transit, a part of Google Maps! Plan your trip on the Web at maps.google.com . More info: Google Maps

Call the RTA Travel Information Center

You can get travel information from the RTA Travel Information Center by calling +1  (312) 836-7000 . Notes:

• The center is open from 6am to 7pm, Monday thru Saturday.
• For faster service, be ready to give your starting point and destination and the day and time at which you wish to travel.
• For RTA Travel Information via TTY, call (312) 836-4949.

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Many third-party transit apps use data from CTA to create trip planners to help you navigate cities on transit, step by step. You can check your device's app store for popular, trusted apps that give transit directions. (We can't control or vet third party apps for you, so use caution downloading third party apps and do so at your own risk.)

Planning a trip yourself

We publish a number of maps to help you find your way.

Additionally, maps are posted in each railcar and station to help you plan your trip when riding the 'L'.

Schedules & Route Guides

Our System Guide helps you find more information about any of our bus or rail routes.

For help determining where to wait for a bus or train, visit our How-To Guides for Riding the Bus and Riding the Train .

Vacation Activities to Include in a Chicago Itinerary

Planning a vacation can be exciting. There are so many vacation activities to include in a Chicago itinerary and countless numbers to choose from. To create an awesome trip though, it's essential to ensure your itinerary includes a variety of experiences. Whether you enjoy outdoor adventures, cultural experiences, or simply prefer to relax on the beach, we have some incredible ideas for you to consider that will help you make the most of your time away.

Whether your trip is to Chicago or other destinations, keep this list handy. It is a great guide for how to make an itinerary. In this post, we'll explore some of the best vacation activities to add to your itinerary, so sit back, relax, and enjoy the read.

Hiking and Nature Exploration

Research local hiking trails and nature reserves.

Make a packing list that includes appropriate footwear and clothing.

Plan for the weather, including bringing rain gear if necessary.

Pack snacks and water for longer hikes.

Ideas for Hiking and Nature Exploration in Chicago

Chicago Lakefront Trail

Bloomington 606 Trail

Starved Rock State Park

Peggy Notebaert Nature Museum

Lincoln Park Zoo

Cultural and Historical Tours

Research local cultural and historical attractions, such as museums or historic landmarks.

Check tour schedules and book in advance if possible.

Find a knowledgeable tour guide who can provide additional context and insight.

Consider taking a walking tour to get exercise while sightseeing.

Ideas for Cultural and Historical Tours in Chicago

African American Heritage Tour of Chicago

Chicago Walking Tour: Historic Treasures of Chicago

Chicago Crime and Mob Tour

Chicago History Museum

Food and Drink Experiences

Research local restaurants and bars that offer unique cuisine or drinks.

Make reservations in advance, especially for popular spots.

Try local specialties and branch out from typical fare.

Take a cooking or mixology class to learn new skills and techniques.

Ideas for Food and Drink Experiences in Chicago

Original Walking Food Experience in Chicago with Tastings

Chicago West Loop Pizza Crawl

Taste of Chinatown Food Walking Tour

Nutella Cafe

Adventure Activities

Research local adventure activities such as high-speed boat rides, helicopter tours, or biking along the lakefront.

Check age and weight restrictions, as well as safety regulations.

Book in advance and allow ample time for the activity.

Bring appropriate gear and clothing.

Ideas for Adventure Activities in Chicago

45 Minute Private Helicopter Flight (1 to 3 People)

Seadog Speedboat Ride

iFly Chicago Lincoln Park

Beach and Water Activities

Research local beaches, lakes, or other bodies of water for swimming, kayaking, or surfing.

Check for any water conditions, advisories, and beach restrictions.

Bring sunscreen, towels, and water-resistant items.

Consider taking a boat tour or fishing trip.

Ideas for Beach and Water Activities in Chicago

North Avenue Beach

Oak Street Beach

Kayak Lake Michigan

Lakefront Fireworks Cruise

Are you ready to have a Windy City experience?

Our ultimate guide to visiting Chicago is your key to unlocking the hidden gems and must-see landmarks.

Plus, we'll share tips from Chicagoans on how to save money and beat the crowds.

Art and Culture Events

Research local art galleries, theaters, or concerts.

Check schedules and purchase tickets in advance if necessary.

Dress appropriately for the event.

Bring a camera to capture memories.

Ideas for Art and Culture Events in Chicago

Chicago Cultural Center

Chicago Center of Architecture

The Art Institute of Chicago

Field Museum of Natural History

Wellness and Relaxation

Research local spas, hot springs, or yoga studios.

Book appointments in advance.

Bring comfortable clothing and a book to read.

Consider incorporating mindfulness or meditation practices.

Ideas for Wellness and Relaxation in Chicago

Waldorf Astoria Spa

Kohler Waters Spa at Lincoln Park

Aire Ancient Baths

Sports and Recreation

Research local sports teams or recreational leagues.

Check schedules and purchase tickets in advance.

Consider trying a new sport or activity, like axe throwing or a batting cage.

Ideas for Sports and Recreation in Chicago

See a game at a local University.

Plan a trip to see a Cubs Game

Bad Axe Throwing 

Chicago Sports Museum

Shopping and Markets

Research local markets or shopping districts.

Check hours and days of operation.

Bring a shopping list and budget.

Consider trying local artisanal goods or handicrafts.

Ideas for Shopping and Markets in Chicago

Magnificent Mile (The Shops at North Bridge, 900 North, Water Tower Place)

Fashion Outlets of Chicago

Randolph Street Market

Maxwell Street Market

Daley Plaza 

Chicago Farmer's Markets (various neighborhoods)

Photography and Sightseeing

Research local landmarks, vistas, or viewpoints..

Check for any necessary permits or access restrictions.

Bring a camera or smartphone with good photo capabilities.

Consider taking a guided tour or using a photography app to enhance your skills.

Ideas for Photography and Sightseeing in Chicago

Chicago Architectural Cruise

Baha'i Temple

Cloud Gate | Millenium Park

The Wrigley Building

DuSable Bridge | Marina City | Chicago Riverwalk

Historic Water Tower

The Chicago Theater

Famous Buildings in Chicago

Family Activities

Research family-friendly activities and attractions.

Check for any age or height restrictions.

Bring necessary gear such as strollers or baby carriers and confirm there are no restrictions.

Consider incorporating educational activities or games.

 Ideas for Family Activities in Chicago

Chicago's Chinatown

Millenium Park

Chicago Walking Tours

The Big Bus Tour

Nightlife and Entertainment

Research local bars, nightclubs, or theaters.

Check hours of operation and dress codes.

Bring identification.

Consider trying local music or performances.

Ideas for Nightlife and Entertainment in Chicago

Comedy Clubs - Zanies | The Second City | The Comedy Bar

Buddy Guy's Legend | Kingston Mines

Howl at the Moon

Tao Chicago

Three Dots and a Dash

Cindy's Rooftop

Chicago Riverwalk - The Northman Beer and Cider Garden | City Winery

Educational Activities

Research local educational institutions or workshops.

Check for any necessary prerequisites or prerequisites.

Prepare to take notes or participate in discussions.

Consider incorporating new knowledge into your itinerary.

Ideas for Educational Activities in Chicago

Adler Planetarium

American Writers Museum

Chicago Children's Museum

Museum of Science and Industry

Relaxing Activities

Research local activities such as meditation, a park or conservatory for meditation, or a quaint  coffee house .

Choose activities that align with your interests and values.

Allow ample time for rest.

Plan for meals and snacks.

Ideas for Relaxing Activities in Chicago

Lincoln Park Conservatory | Alfred Caldwell Lily Pool

Garfield Park Conservatory

The Art Institute of Chicago South Garden

Nature Boardwalk at Lincoln Park Zoo

Chicago Botanic Garden

Humboldt Park Garden

In conclusion, planning an itinerary that has a range of activities is key to having a memorable and unique vacation experience. By checking hours of operation, location, and booking in advance, and allowing ample time for each activity, you can make the most of your visit.

What are some tips for creating a vacation itinerary?

Research local activities and attractions, consider your interests and values, and book in advance when possible.

How can I ensure that my vacation activities are safe?

Check for necessary permits and safety regulations, bring appropriate gear and clothing, and choose reputable service providers.

What are some family-friendly vacation activities?

Consider visiting local amusement parks, museums, or zoos, or participating in outdoor activities like hiking or biking.

How can I make the most of my vacation downtime?

Consider incorporating relaxing activities like meditation or a spa day, or simply allowing time to unwind and recharge.

What are some unique vacation activity ideas?

Consider trying new foods, taking a guided tour or class, or volunteering for a local community organization.

Did you learn something new? Please like and share with friends.

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coming for 2 days on day 1 we plan go to

maggie daley park

buckingham fountain

90 min river cruise

magnificent mile

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• SUMMER Outdoors - 606 Elevated Trail, Riverwalk, Maggie Daley Park, Northerly Island
• Chicago BEARS Info and Getting to SOLDIER FIELD for a Game or Concert
• Buying CUBS Tickets and Visiting Wrigley Field
• WHITE SOX Info and Visiting Guaranteed Rate Field
• _______Chicago's Best Food and Drink________
• Best Restaurants
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• Dining and Drinking Outdoors or with a View
• Chicago Pizza - The Great Debate
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• ________Trip Reports and Miscellaneous_______
• Overnight Parking in Chicago for RV Motorhomes, Trucks, Boats
• Trip Reports
• Trip Reports - continued

From saving on gas to driving with kids, here's your ultimate road trip planner

"Easy Travel” is a 10-part series focusing on how to reduce bumps during vacations, anticipate roadblocks and be ready when things aren’t going your way. If you'd like to contribute to our future reporting and share your experience as a source, you can click here to fill out this quick form .

Ina Daly has spent most of her life on the road.

“My dad was a truck driver and that led me to becoming a truck driver,” she said. “What we do in a day, on a daily job would be like a long road trip to most people.”

With nearly 40 years of driving for freight transportation services provider XPO and numerous industry accolades under her belt, including grand champion at this year’s Arizona Truck Driving Championship , Daly is a pro. She’s also a mom and a grandmother who’s happy to share her experiences to make everyone’s road trips better.

“Some of the things I'm telling you are what we truckers tell our family members,” she said. “I've had a lot of accomplishments in my career and going to the National Truck Driving Championships (this month) is a reward, but the bigger reward is being able to share some things … that have the potential to save lives.”

What to do before a long drive

“Make sure that your vehicle’s road trip ready,” Daly said. ”Really pay close attention to your tires, your coolant, your fan belt.”

She notes tire dealers often offer free inspections to ensure tires are properly inflated and undamaged.

AAA spokesperson Aixa Diaz advises getting the whole car serviced before hitting the road.

“If you're a car person and you can, do that yourself at home, by all means,” she said. Otherwise, she recommends getting the oil changed and battery and tires checked professionally. 

To save time and avoid stress, Diaz also suggests filling up on gas the night before leaving and making hotel reservations well in advance, noting that many hotels allow cancellations without penalty up until the day beforehand. 

What do you need before a road trip?

It’s always good to keep an emergency kit with supplies like first aid, a flashlight and extra batteries, and basic tools in the vehicle.

“You want to make sure that if you do have a tire issue, you have the proper tools and jacks in your vehicle to be able to change it,” Daly said. She said warning signals like reflective triangles can also warn other drivers to steer clear in the event of a breakdown.

For road trips, both she and Diaz recommend shelf-stable snacks like protein bars that won’t melt and plenty of water. “Don't think that a bottle or two for everybody is enough,” Daly said. “You've got to have, you know, five or six bottles for everyone.” 

Diaz also recommends wet wipes, blankets during the winter, and any time-sensitive medication or pet food that might be needed in the event of an extended delay.

“These things ideally wouldn't take up too much room in your trunk but they're just good to have in case of an emergency,” Diaz said. “Just think, ‘If I were stuck for a long time, what would keep me comfortable until I was able to (get) help?’”  

A printed map and a general sense of the route can also help in case there GPS hiccups or a phone dies.  AAA’s free TripTik planner can help travelers plot their trips in advance and find rest stops, lodging, food and gas along the way. And its free Gas Cost Calculator can help locate the cheapest average gas prices for drivers when it’s time to refuel.

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What I should know before a road trip?

“Everything can be a distraction in the car – the radio, the kids, etc. But the phone is a big one,” Daly advised. “When you’re driving, that thing should not ever be in your hand.”

More than 3,500 people were killed on U.S. roads in 2021 because of distracted driving, according to the National Highway Traffic Safety Administration . 

Daly also recommends watching out for distracted drivers.

“You can tell a distracted driver by their fluctuating speed,” she warned. “They're drifting in their lane. Their head is looking down instead of focusing on the road. You want to give those people a wide berth.”

How long will a road trip take?

Road trips always take longer than expected because of traffic, construction and other things that arise en route.

Diaz says to expect at least an hour longer than whatever the GPS predicts. Daly recommends leaving at least two hours early.

“You don't want that stressful drive,” Daly said. “You’re hurrying. That lends to bad driving behaviors like tailgating and speeding, which leads to accidents. Don’t put yourself in that situation.”

How many hours a day should you drive on a road trip?

“It just varies so much from person to person, how long they’re comfortable driving,” Diaz said. “We want to err on the side of safety. We want people to be safe on the roads and drive the speed limit and not rush it, but everybody's different.”

Switching out drivers can lighten the load, but no matter who is driving, Daly said, “If you're starting to feel a little, less attentive, maybe a little fatigued, it’s time to take a break.”

What time is best to drive?

“We always recommend, especially during the holidays, leave early in the morning,” Diaz said. “The later you leave in the day, the worse it's going to be because a lot of times during the week … you're going to mix with those commuters on the road.”

“Some people enjoy night driving,” she added. “Once you get to like 8 p.m., 9 p.m. traffic comes down a lot.” 

However, she noted drivers who leave in the evening should watch out for fatigue and plan to drive less than if they started fresh in the morning.

How do you take a good road trip with kids? 

When possible, Daly recommends having a designated passenger to help with kids so the driver can focus on the road.  

Another important thing is to keep seatbelts on the whole way.

“Kids have a tendency to take those off,” Daly said. “Make sure they stay buckled up. I've seen some horrible things out there.”

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What do kids need on a road trip?

Entertainment helps pass the time, but it doesn’t have to be digital. There are all sorts of screen-free road trip games . 

Diaz recommends printing a map or list of sites or cities for kids to watch for along the way.

“You know, yell it out or mark it on your sheet,” she said. “Have some crayons in the car with them so they're following along on the trip, and they feel like they're part of it.”

“Point out historical landmarks and scenery; enjoy nature,” Daly echoed. “That's one of the things that we truck drivers love about our jobs is we get to see the country and nature.”

Stop at points of interest every few hours or simply for everyone to stretch their legs.

And for those times when kids are on screens, make sure to pack car chargers.

What is the best way to save gas?

Don’t speed. 

“Fuel economy peaks at around 50 miles per hour on most cars, and then it drops off as the speeds increase,” Diaz said. “You think, ‘OK, if I just go 70, I'm going to get there faster, and it'll be better,’ but essentially, you're just wasting gas at that point." Fuel economy can be increased by as much as 15% by reducing highway speeds by 5 to 10 miles per hour, she said.

Don’t idle unnecessarily either, like at rest stops.

“Your car engine consumes about a quarter to a half a gallon of fuel per hour while it's idling,” she said. “But a warm engine only takes about 10 seconds’ worth of fuel to restart, so if it's safe to do so, just shut off your engine.”

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What happens if my tire blows out?

“When you blow a tire, kaboom, it freaks you out. Do not panic,” Daly said. “Don't slow down abruptly or brake hard or jerk the wheel because that will cause you to lose control and have an accident.”

“Just focus on steering,” she added. “Slow very gradually, off to the side of the road in a safe area, and you won’t have any issue from your blown tire.”

How do you drive around semitrucks?

“Be aware of our needs and limitations,” Daly said. “You know we’re big. We need a lot of space around us. We have big blind spots. … If you can’t see the truck driver’s face in the mirrors of the truck, the truck driver can’t see you.”

She advised against passing on the right. 

“If you have to pass quickly, don’t linger over there. We see people driving over there for the shade (and it) puts us in a very dangerous situation,” she said. “And don’t cut in front of us and then hit your breaks. People don’t like to follow a truck because they can’t see around us, so they pass us and then cut in front of us.”

“It takes away that safety cushion we leave in front of us,” she added. “When you see all that space in front of a truck, that's not for your convenience so that you can pass us and cut into it. That’s for our safety and yours.”

By the same token, she advised fellow drivers to leave plenty of space in front of their own vehicles, so they have enough room to stop quickly in an emergency. If another driver cuts into that space, she suggested, “Take a break. Slow down again. Recreate that space. Bite your tongue and think pure thoughts.”

That last tip may not be so easy.

What has been your best or worst road trip experience?