tourist attractions in chicago downtown

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15 Best Things to Do in Downtown Chicago

When you’re visiting Chicago, head for the downtown district and you’ll be in The Loop. It’s more than an urban spread of cloud-high skyscrapers and cultural recreation centers. You’ll be amazed by what you find.

The Loop is a community area of the city which covers over one and a half square miles, is fronted by the stunning shoreline of Lake Michigan and backed by the Chicago River. There are lakeside trails, riverside walks, and enormous parks as well as museums, art galleries, and historical monuments.

While you may be in the city, you can be forgiven for thinking you’re in a coastal resort as there are several beaches within a few minutes of the Loop too. Downtown Chicago really is a suburb of the city which has it all and more. Don’t miss out on any of these fifteen fantastic things to do while you’re there. You’ll be kicking yourself if you do.

1. Boat Cruise

By day or night one of the best ways to take in the Loop skyline is from on the water. Board a boat at the Navy Pier and be prepared to be impressed by sights of Downtown Chicago as you sail by. Whether you take a cruise down the Chicago River or on Lake Michigan, you’ll get stunning and unforgettable panoramic views of iconic buildings and the Loop’s prominent monuments.

There are lunch, brunch or dinner cruises. Cruises for sightseeing or ones which offer educational information on the city’s architecture. For adrenaline junkies, there are speedboat tours and extreme thrill rides which will get your heart pumping as you speed over the water at 45 mph.

For the romantics, watch the fireworks display on Navy Pier light up the night sky from a cruise boat. Combine that with dinner onboard and a spot of dancing for a perfect night out Loop-style.

2. The Picasso

Catch an eyeful of The Picasso. An arresting, unnamed sculpture which dominates the Loop’s Daley Plaza. The weighty steel sculpture stands around fifty-foot tall, and is the subject of an ongoing, fifty-year long debate as to what it actually represents.

Is it a winged horse, a dog or a Cubist representation of a preferred model? Your guess will be as good as anyone else’s. The Picasso, or the Chicago Picasso, which was a gift to the city from the famous French artist, makes an unusual and outstanding presence in the plaza. The sculpture has also been a background prop in several well-known movies and as strange a visage as it has, it’s surprisingly photogenic.

The sculpture makes an interesting centerpiece in the plaza during the festive or farmer’s markets and music events which are held there regularly.

Related tour : Chicago’s Modern Skyscrapers Guided Walking Tour

3. Pizza, Popcorn & Pumpkin Pie,

There are three things you just have to try when you’re in Downtown Chicago. They’re all iconic foodstuffs which the city claims to have created or has adopted as its own.

Chicago-style pizza is double deep-dish high and when its cut, as thick as a slice of cake. Oozing with chunky tomato sauce, melted cheese and layer upon layer of whatever other ingredient takes your fancy, it’s been a staple comfort food of the city for over seventy years. Sink your teeth into a slice at Pizano’s on Madison Street or Giordano’s on Randolph Street.

Chicago-style popcorn is an unusual, but tasty combination of two different flavors of popcorn. Cheesy kernels are mixed with others which have been coated with caramel for a unique taste sensation which has not just Chicago, but the whole state of Illinois, addicted. No one knows for sure how it came about and no one’s too worried so long as they keep making it. You can get yourself a bucketful at Garrett’s on E Madison Street.

The official pie of the state of Illinois is pumpkin pie. Spiced with cinnamon and with a pastry crust base to keep all that pumpkin custard under control, it’s a filling sweet treat. Don’t miss out on grabbing a slice or two while you’re in the Loop.

4. Willis Tower Skydeck

The Willis Tower or the Sears Tower as it’s also known once held the number one position as the tallest building in the world. While it’s now been surpassed by several others, its observation deck is still the highest in the US at one thousand three hundred and fifty-three dizzying feet. There are incredible views of Chicago and Lake Madison through the deck’s windows.

If you’ve got the nerve, you can make the experience even more memorable. Step onto The Ledge, a glass-walled and glass-floored box which juts four feet out of the building – one hundred and three floors above the ground.

If you’re on the Ledge and feel as if you’re developing vertigo, don’t worry. It’ll just the building swaying in the wind.

Book online : Chicago Skydeck Experience Ticket

5. Lakefront Trail

The Lakeside Trail is a nineteen mile long, asphalt and concrete pathway which runs adjacent to Lake Michigan shoreline from the South Shore Cultural Center in Chicago to the city’s Kathy Osterman Beach. Part of the trail runs through the Loop, and it’s the ideal place to get some fresh air and exercise.

Renting a bicycle or a pair of inline skates is a fun thing to do if you don’t want to walk or jog. You can access the trail from Grant Park or E Monroe Street as well as various other points throughout the Loop.

Riding or walking out to the Adler Planetarium is recommended. You’ll get some great views of the Loop skyline from there.

6. Historic Route 66 Sign

Head to East Adams Street, just off South Michigan Avenue in Downtown Chicago and look up. You’ll find a surprising historic monument there which will make a great photo for your Instagram account. Snap a shot with the historic Route 66 sign to get your own personal memento of the iconic highway.

Route 66 is probably the most well-known highway in the world and has been immortalized in films, songs and stories. The original road was almost four thousand miles long and stretched from Chicago right the way across the US to Santa Monica in California. It begins, and ends, in the Loop.

7. Grant Park

Grant Park is the Loop’s three-hundred and nineteen-acre green space which is bordered by Lake Michigan. Its wide boulevards are perfect for strolling; there are numerous flower gardens, fountains, monuments, and a three-acre skate park.

Inside its boundaries, Grant Park encompasses three other parks, the Millennium, the Maggie Daley and the Hutchinson Field, which offer visitors access to sporting facilities and artwork. Two marinas, a university campus and the Art Institute of Chicago. It’s also where the Petrillo Music Shell, the Cloud Gate and the Buckingham Fountain are. All of those, you can read about further on.

The park hosts amazing food and music festivals throughout the year. Time your visit to coincide with The Taste Chicago, Lollapalooza or the Chicago Blues Festival and you’ll see the park thronged with crowds.

Don’t miss out on seeing the Agora, a weird and wonderful sculpture comprised of over a hundred headless and armless figures. It’s definitely photo-worthy.

8. Buddy Guy’s Legends

When you’re in Downtown Chicago, there’s one thing you have to do, and that’s listen to some Blues. In the Loop, one of the best clubs to do that is Buddy Guy’s Legends.

The club is owned by Blues legend Buddy Guy, winner of seven Grammy awards plus a whole lot more and has influenced more musicians than he’s had hot dinners. Now at the age of eighty-one, he’s not on the stage every night, but other top Blues musicians are.

There are live shows nightly and an in-house restaurant which serves Louisiana soul food in honor of Buddy’s ancestral roots.

9. Cloud Gate

The Cloud Gate is one public sculpture you can’t walk past without noticing. The one hundred ton, shiny stainless steel “bean” which was inspired by a droplet of mercury, is eye-boggling.

The Cloud Gate is in the AT&T Plaza in Millennium Park. Walk underneath the Gate’s arch and look up to see a distorted version of yourself and those around you. It’s an unusual experience.

Stand at a distance from the Cloud Gate to capture a photo of the Loop’s twisted skyscrapers reflected on the sculpture’s curved surface. Amazing.

10. Loop Retail Historic District

The Loop Retail Historic District is much more than departments stores. This area of the Loop which covers over twenty-six acres is full of historic buildings and landmarks which are just as interesting from the outside as they are on the inside.

If you feel the need to shop, step into Macy’s on State Street. The store covers a full eight floors of retail space and ranks as the second largest store in the world. Clock the two seven-ton timepieces attached to the corners of the building before you go in because once you’re inside, you’ll forget about time completely.

11. Riverside Walk

Wander down the Loop’s Riverside Walk, and you’ll find more than a towpath running alongside the water.

The mile and a quarter long paved pathway is lined with beer gardens, restaurants with terraces and cafes. More than just a walk by the riverside, the Riverside Walk is one of the best social hubs in Downtown Chicago.

Don’t miss out on trying a traditional and handmade Italian ice cream from the old-fashioned handcart. Their flavors are to sigh for.

12. The Art Institute Of Chicago

The Art Institute of Chicago, on South Michigan Avenue in Grants Park, may be housed in what looks like a forbidding mausoleum, but inside it’s an absolute trove of treasures.

It takes a full day to browse around as there is so much to see. The museum has over three-hundred thousand permanent exhibitions plus hosts countless temporary exhibits throughout the year.

The artworks are not restricted to American artists. There are numerous and varied collections displaying the works of notable artists from all over the world in multiple forms which range from oils and watercolors to photographs, prints, textiles, and furniture.

Book online : Art Institute of Chicago Skip-the-Line Ticket

13. Buckingham Fountain

The Clarence Buckingham Memorial Fountain, to give it its full title, is not only the centerpiece of Grants Park and the symbolic feature of the city of Chicago, it is one of the largest fountains in the world.

The magnificent fountain is tiered in layer upon layer of pink marble, surrounded by eight seahorses and has a central jet which spurts water to a phenomenal height of one-hundred and fifty feet.

Catch the hourly water shows from the middle of April through to mid-October or the evening performances when the sprays dance in rhythm with lights and music. Impressive.

14. Petrillo Music Shell

If there’s an outdoor music festival happening in the Loop, it’ll be happening at the Petrillo Music Shell in Grants Park.

The Shell houses a massive stage plus all the high-tech sound and lighting equipment needed to satisfy even the most discerning of performers and audiences. It’s fronted by tiered seating for five thousand and enough lawn space to accommodate thirty thousand spectators more.

Whether you watch the live bands performing at the Taste of Chicago or attend the Chicago Blues Festival there, guaranteed, the atmosphere will be buzzing.

15. Miller’s Pub

Eat, drink and maybe spot a celebrity at one of the Loop’s oldest establishments. Miller’s Pub, on S Wabash Street, has been operating since 1935 and has been in the ownership of its current proprietors since 1950.

Check out the gallery of famous faces on the picture wall, then sit back in one of the booths and enjoy a rack of Miller’s infamous ribs or their trademarked, HenryJ corned beef hash followed by a slice of Key Lime Pie.

Miller’s is a Loop tradition, don’t miss out on dining there.

15 Best Things to Do in Downtown Chicago:

• Boat Cruise
• The Picasso
• Pizza, Popcorn & Pumpkin Pie,
• Willis Tower Skydeck
• Lakefront Trail
• Historic Route 66 Sign
• Buddy Guy's Legends
• Loop Retail Historic District
• Riverside Walk
• The Art Institute Of Chicago
• Buckingham Fountain
• Petrillo Music Shell
• Miller's Pub

Chicago   Travel Guide

Courtesy of jaskoomerovic | Getty Images

28 Fun Things to Do in Chicago

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Millennium Park and Cloud Gate Millennium Park and Cloud Gate free

U.S. News Insider Tip: Construction around the Cloud Gate sculpture will limit the public's access to this top tourist attraction until spring 2024. While you might not be able to snag a selfie with "The Bean," many other attractions are available within the park. – Cortney Fries

A first-time visit to Chicago isn't complete without a stop at Millennium Park. Situated in the Loop just north of the Art Institute of Chicago , this 25-acre space is used to showcase cutting-edge art, architecture and landscaping; it also acts as a backdrop for concerts and festivals.

Grant Park and Buckingham Fountain Grant Park and Buckingham Fountain free

U.S. News Insider Tip: If you're visiting Chicago Sept. 8 through 10, head to Grant Park early – around 11 a.m. to avoid the lines – for the Taste of Chicago. Enjoy the park and eat the best cuisine the city has to offer. Admission is free. – Sarah Estime

Often referred to as "Chicago's front yard," Grant Park is an approximately 313-acre swath of green space that starts at the eastern edge of the Loop and stretches down to the northern fringes of the Near South Side.

Art Institute of Chicago Art Institute of Chicago

Home to one of the country's most impressive collections of impressionist and post-impressionist art (plus works from numerous other genres), the expansive Art Institute of Chicago features nearly 300,000 works from all over the world in its permanent collection. You'll find pieces created in the Byzantine era, as well as paintings completed just a few decades ago.

Highlights include Jacob Lawrence's "The Wedding," Georgia O'Keeffe's "Sky above Clouds IV" and Grant Wood's "American Gothic." The Art Institute's exhibits also include all sorts of intriguing artifacts, from European armor to the Thorne Miniature Rooms, which showcase interior design and furnishings in Europe and America from the late 13th to early 20th centuries. In addition to the permanent collection, the Art Institute hosts traveling exhibitions covering a variety of subjects and showcasing a diverse array of artists and genres.

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For shopping at more than 450 retailers within walking distance in downtown Chicago, make your way to The Magnificent Mile.

Navy Pier Navy Pier free

Extending out onto Lake Michigan, Navy Pier offers plenty in the way of family-friendly entertainment.

The first thing you'll spot once you set foot on the pier is the towering Ferris wheel (which stands 196 feet tall); you'll also find a drop tower and a carousel. Once the kids have had their fill of thrill rides, you can spend some time cruising the Chicago River on a sightseeing or speedboat tour or spend a few hours exploring the Chicago Children's Museum , with hands-on exhibits ranging from treehouses to fire trucks.

Lincoln Park Zoo Lincoln Park Zoo free

U.S. News Insider Tip: North Avenue Beach is a short walk over the North Avenue Bridge when you park at the southern end of the Lincoln Park Zoo lot. Explore the zoo, then stroll over to the beach for an afternoon in the sand. – Cortney Fries

Located 2 miles north of the Loop in the North Side neighborhood of Lincoln Park, the Lincoln Park Zoo is home to nearly 200 species, such as zebras, sloths and hippos. Visitors can view the zoo's furry (or scaly) friends in their natural habitats: Check out the gorillas in the sprawling, award-winning Regenstein Center for African Apes, or head to the Kovler Seal Pool to get up close and personal with harbor seals. Seal training and feeding occurs daily at 11:30 a.m. and 2 p.m.

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One of Chicago's most notable attractions is its skyline, and one of the best places to experience it is at the 360 CHICAGO Observation Deck.

Formerly known as the John Hancock Observatory, 360 CHICAGO towers 1,000 feet over The Magnificent Mile from its location on the 94th floor of the John Hancock Center (or 875 North Michigan Avenue as its more formally known). Encased by floor-to-ceiling windows, 360 CHICAGO boasts expansive views of the city; on a clear day, you can see four states. Meanwhile, the interactive screens will help you identify different landmarks that appear in your panorama.

The Field Museum The Field Museum

U.S. News Insider Tip: After hours of museum hopping, grab a kid-approved lunch at Kim & Carlo's Hot Dog Cart. The no-frills stand offers everything from vegan dogs to the traditional Chicago hotdog. Enjoy your lunch on the water. – Sarah Estime

This extensive natural history museum occupies half an acre of Grant Park 's Museum Campus and houses exhibits that showcase artifacts from multiple eras and destinations, making it a must-see for kids (as well as any fans of the "Indiana Jones" movies).

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Though several companies, including Wendella Sightseeing Co. and Chicago Line Cruises, offer architecture river cruises, most travelers recommend climbing aboard a Chicago's First Lady Cruises boat with a Chicago Architecture Center docent. You'll learn tons of information about the area's architecture, plus catch superb skyline photo-ops.

Maggie Daley Park Maggie Daley Park free

U.S. News Insider Tip: There are many restaurant options around the park, but Wildberry Pancakes & Café is a satisfying brunch spot. Choose from creative pancake options, a variety of omelets, crepes, sandwiches and salads. Go hungry and leave happy. – Cortney Fries

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Griffin Museum of Science and Industry Griffin Museum of Science and Industry

U.S. News Insider Tip: Mid-November through the first week of January, experience the annual "Christmas Around the World" and "Holidays of Light" exhibits. Volunteers decorate more than 50 trees in celebration of holiday traditions from around the globe. – Cortney Fries

Chicago's extensive Griffin Museum of Science and Industry is the Western Hemisphere's largest science museum, showcasing more than 35,000 artifacts and a variety of hands-on exhibits meant to inspire creativity. The museum resides in the 14-acre former Palace of Fine Arts, which hosted the famous World's Columbian Exposition in 1893. The fair brought together some of the world's greatest scientific minds, including Thomas Edison and Nikola Tesla, who at the time were competing to prove which type of electricity – direct current or alternating current – was more effective. 

Wrigley Field Wrigley Field

U.S. News Insider Tip: If you're visiting during the holiday season, don't miss Winterland at Gallagher Way for family-friendly rides and games inside and around the ballpark. Christkindlmarket Wrigleyville is free to enter. Enjoy festive shopping and international food and beverage selections. – Cortney Fries

Chicagoans take their love of sports very seriously. So, for a real taste of Chicago culture, head north of the Loop to Wrigley Field to watch the Chicago Cubs play ball at the Friendly Confines. History buffs will also appreciate this sports treasure, which first opened in 1914 and holds the honor of being the second-oldest Major League Baseball stadium in the country (after Fenway Park in Boston ).

Shedd Aquarium Shedd Aquarium

U.S. News Insider Tip: If you're visiting in the summer (June through August), check out Jazzin' at the Shedd. You can enjoy jazz music and drinks with incredible views from the terrace. Plus, the lights dim in the aquarium for a unique experience. – Elizabeth Von Tersch, Senior Editor

Shedd Aquarium is one of the world's largest indoor aquariums, housing around 32,000 creatures. While you're here, you can feel stingrays float beneath your fingers, listen to sea lions bark and learn all about a variety of turtles. A visit to Shedd Aquarium will lead you through a cornucopia of habitats, where you'll find additional animals like penguins, piranhas, sharks and beluga whales. Or, for an additional fee, you can participate in specialty experiences like animal encounters, feeding experiences and virtual reality.

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Skydeck Chicago at the Willis Tower Skydeck Chicago at the Willis Tower

More than 1.7 million people make their way to Willis Tower's Skydeck Chicago each year, and it's easy to see why. Occupying the 103rd floor – that's nine floors higher than 360 CHICAGO – of the 110-story Willis Tower (the third-tallest building in North America after One World Trade Center and Central Park Tower), Skydeck Chicago boasts breathtaking views of the city. Visit on a sunny day and you may be able to see far beyond Chicago's borders to Indiana, Michigan, Wisconsin and other parts of Illinois.

The highlight for most visitors is the Ledge. Extending 4.3 feet beyond the building's exterior, this platform is made entirely of glass – even the floor. Travelers also liked the video screens that show what it would be like to stand 103 floors above other Chicago attractions, including Wrigley Field and Millennium Park . However, long lines quickly form for Skydeck Chicago, so plan on arriving early or purchasing a Chicago CityPASS, which covers expedited admission into the attraction. Or, simply pay extra for expedited entry, which features an express line to the elevators. For the best views, it's advised that you visit just after opening or after sunset. If you'd like to enjoy the sunset from the tower, plan on arriving 30 to 45 minutes before sunset to ensure you have enough time to get through the elevator line and up to the top.

North Avenue Beach North Avenue Beach free

Located in Lincoln Park directly on Lake Michigan, North Avenue Beach is one of the most popular swimming spots in Chicago.

The sandy beach has volleyball courts, plenty of space for visitors to stretch out and multiple things to do near nearby. Plus, it offers spectacular views of the city skyline. Beachgoers can also find restaurants, sports rental companies, restrooms and more inside a 22,000-square-foot beach house adjacent to the shore.

The Second City The Second City

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Recent reviewers said that everyone in their group could not stop laughing during the shows, which typically last 90 minutes to two hours. Ticket prices vary by the show and date, but run anywhere from $30 to $100.

The Chicago Theatre The Chicago Theatre

Aside from Cloud Gate and Buckingham Fountain , The Chicago Theatre's red and yellow marquee is perhaps one of the city's most recognizable landmarks. Illuminating North State Street at the northern edge of the Loop, The Chicago Theatre first opened its doors in 1921 as an extravagant movie theater and performance venue. Throughout its history, the theater has hosted such big names as Duke Ellington, Diana Ross and Prince, in addition to screening blockbuster flicks. Though the theater fell into disuse in the 1970s, new management and a full renovation in the 1980s helped return the venue to its former glory. Today, the theater is still used for a variety of comedic, theatrical and musical performances.

According to past patrons, the theater's historic appearance enhances the overall experience of catching an event here. Just remember, cameras and video cameras, including those on cell phones, cannot be used during tours or performances.

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Located at Navy Pier , the Chicago Children's Museum offers temporary and permanent play-based exhibits for babies, toddlers and kids ages 4 and older. Founded in 1982 by the Junior League of Chicago as a response to cuts in arts programming, the museum was originally housed in two hallways of what is now called the Chicago Cultural Center . Today, children can dig for "teeth" and "bones" in "Dinosaur Expedition," climb through tunnels of "Cloud Buster," test their STEAM (Science, Technology, Engineering, Art and Math) skills in the Tinkering Lab and paint, draw or sew in the art studio.

Recent visitors appreciated the interactive, hands-on exhibits, which they recommend for young children.

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U.S. News Insider Tip: Across the street from the museum, you will find the first Nutella Café, where you can savor French and Italian dishes featuring the heavenly hazelnut spread. The gelato is roll-your-eyes-to-the-back-of-your-head good. – Cortney Fries

The first museum in the United States dedicated to celebrating the diverse voices and influence of American authors, the American Writers Museum is an interactive journey through more than five centuries of written and spoken word. This relatively small museum, which opened in 2017, features thoughtful and reflective exhibits that you can touch, smell, hear and see. 

DuSable Black History Museum and Education Center DuSable Black History Museum and Education Center

U.S. News Insider Tip: If driving in Chicago isn’t your thing, consider taking the No. 55 bus to the museum. The bus drops you off within just a five-minute walk of the museum. – Sarah Estime

The DuSable Black History Museum and Education Center, named for Jean Baptiste Pointe DuSable, the entrepreneur who is credited with founding Chicago, is a must-visit for anyone looking to learn more about African American history in the city of Chicago and America. It celebrates its 62nd anniversary in 2023, and is full of thought-provoking exhibits, including those that showcase fine art created by influential African American artists and historical materials. Note that visitors hoping to enjoy “The March” exhibit, an immersive experience depicting the historic March on Washington and Martin Luther King Jr.'s "I Have A Dream" speech, can go in groups of no more than four at a time.

Adler Planetarium Adler Planetarium

The first planetarium in the Western Hemisphere, the Adler offers unrivaled insights into our solar system. Indeed, "Our Solar System" is one of its permanent exhibits, along with "Mission Moon," "The Universe: A Walk Through Space and Time," "Telescopes: Through the Looking Glass" and "Astronomy in Culture," among others. Its facilities include the Doane Observatory, which has the largest telescope available to the public in the Chicago area, through which visitors can glimpse celestial objects trillions of miles away. The Adler also has three full-size theaters – the 3D Universe Theater, the Definiti Space Theater and the Grainger Sky Theater – in which it screens programs like "Destination Solar System," "Planet Nine" and "One World, One Sky: Big Bird's Adventure."

Space enthusiasts invariably find the Adler's presentations both informative and entertaining, if somewhat pricey. Most visitors suggest setting aside a few hours to explore the various exhibits and shows. Travelers recommend maximizing your parking expenses by also visiting the Shedd Aquarium or The Field Museum , which also sit on the Museum Campus. Reviewers also appreciated the Lake Michigan and skyline views as seen from the planetarium.

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U.S. News Insider Tip: If you’re looking for unique souvenirs from your Chicago trip, consider The Goddess & Grocer for its gift baskets. – Sarah Estime

In Chicago, you can find eye-catching street art nearly everywhere. As you sightsee, you’ll be greeted with unique, thought-provoking art on the sides of buildings and underneath bridges. If you’re looking for an experience that walks you through the history and cultural significance of Chicago's street art scene, look no further than the Offbeat Street Art Tour. On this two-hour tour, you’ll discover new artists and learn the inspiration behind their colorful works, along with some interesting neighborhood history. You’ll also be able to take great photos along the way.

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The Green Mill The Green Mill

U.S. News Insider Tip: For visitors looking for a bite to eat after a night of jazz music, head across the street to Damera for an authentic Ethiopian meal, or down the block to the Fat Cat for a burger. – Sarah Estime

Best known for serving gangsters during its speakeasy days, the Green Mill invites travelers to step back in time. The long bar that runs along the club's left side sits in front of smokey mirrors and is peppered with decor reminiscent of the Prohibition era. The entire place is cast in a warm reddish glow while old-time jazz plays from the jukebox. The bar – one of Al Capone’s favorites – has no set menu; order whatever cocktails you like (though the chocolate martinis are delicious). There is also a selection of beer and wine.

Garfield Park Conservatory Garfield Park Conservatory free

One of the biggest botanical conservatories in the United States, the Garfield Park Conservatory houses thousands of plant species in eight indoor gardens, as well as 10 acres of outdoor gardens.

Each indoor space has a distinct focus. The Aroid House features varieties of its namesake, which are among the most popular houseplants; it also features sculptures by the world-renowned glass artist Dale Chihuly made specifically for the Aroid House. As its name suggests, the Desert House boasts cacti and succulents, while the Fern Room arranges ferns around an indoor lagoon. The Palm House, the conservatory's largest structure, recreates a tropical landscape complete with more than 70 palm trees. Meanwhile, the Elizabeth Morse Genius Children's Garden aims to educate little ones about plants. Horticulture Hall displays a range of flowers and plants and also has tables where visitors can take a seat and have a rest.

The Richard H. Driehaus Museum The Richard H. Driehaus Museum

Occupying a restored mansion built in 1883, the Richard H. Driehaus Museum presents exhibitions relating to architecture, art and design from the 19th century to the present day.

The Nickerson Mansion containing the museum boasts an entrance hall made with so much marble that the building was nicknamed "the Marble Palace." (The museum takes its current name from the philanthropist who founded it in 2003.) Its reception room features intricate woodwork as well as items from the museum's permanent collection, such as a Tiffany Studios lamp that dates back to the early 1900s. Meanwhile, the front parlor displays Renaissance Revival furniture original to the Nickerson Mansion. The dining room, fitted with elaborately carved oak, houses a silver punch bowl first exhibited at the 1893 World's Columbian Exposition. Other highlights from the permanent collection include a gem-encrusted inkstand, a ceramic clock, multiple chandeliers, paintings, sculptures and an array of decorative items.

Chicago Cultural Center Chicago Cultural Center free

The "People’s Palace," a popular destination occupying a full city block in the downtown Loop neighborhood, is a stunning architectural marvel as well as a venue for a great deal of cultural programming, including art exhibits and concerts. Among its features are one of the largest Tiffany stained-glass domes in the world (made with around 30,000 individual pieces of glass) and a marble lobby adorned with mosaics made of gold, glass and precious stones.

Visitors invariably rave about the impressive structure and its elaborate decorations, saying it’s worth it to pop in for free to see the ornate ceiling.

University of Chicago University of Chicago free

Founded in 1890 by John D. Rockefeller, the University of Chicago is an urban research university in the city's Hyde Park neighborhood close to Lake Michigan. Currently, it has more than 7,000 undergraduate students and more than 10,000 graduate, professional or other students as well as nearly 2,400 full-time faculty members.

Impressive as those statistics may be, they aren't reasons to visit. But the university's 217-acre campus, which was designated a botanic garden in 1997, and its mixture of English Gothic and modern architecture are. Some of the newer structures were designed by celebrated architects like Ludwig Mies van der Rohe and Eero Saarinen, while some of the older ones are adorned with gargoyles that date back to the 1893 World Columbian Exposition. The university welcomes visitors to explore its campus, and provides information about its architecture on its website. Those who've visited before routinely call the buildings diverse and beautiful, and many recommend stopping by in the spring when flowers bloom across campus, or fall when amber leaves transform the grounds.

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Why we love it

How long do you have? The Loop is the heart of the city and it’s bursting with iconic Chicago attractions, including historic architecture, river cruises, Millennium Park, the Chicago Riverwalk, a vibrant theatre district, incredible dining, shopping along State Street…and that’s just for starters.

Explore like a local

• Kayak the Chicago River on a guided tour for jaw-dropping views of some of the city’s most iconic architecture.
• Explore the architectural greatness hidden inside the Chicago Cultural Center , where you’ll find free exhibits, live shows, a maker marketplace, and more.
• Catch a free concert or movie screening under the stars in Millennium Park , a favorite local activity in the summer.

Insider tips

As Chicago’s official downtown area, the Loop is celebrated for its dynamic architecture and big city buzz. To get a grasp on the area’s architectural legacy, start your visit with one of the many great architecture river cruises , like the Chicago Architecture Foundation Center River Cruise aboard Chicago’s First Lady Cruises.

The Loop is also home to the award-winning Chicago Riverwalk , a pedestrian-only pathway lined with great waterfront restaurants, the McCormick Bridgehouse & Chicago River Museum, and the mind-blowing digital art display Art on theMART.

On the lakefront side of the Loop, you’ll also find the Millennium Park campus — home to iconic Cloud Gate (aka “The Bean”) , Crown Fountain, peaceful Lurie Garden, and the Jay Pritzker Pavilion that hosts legendary music festivals like the Chicago Blues Festival , Chicago Jazz Festival , and a free summer music series and film series . Right next door, you can rock climb, skate, and play at whimsical Maggie Daley Park .

Get your culture fix at the historic Art Institute of Chicago , one of the top museums in the world according to TripAdvisor. It’s also one of the oldest and largest art museums in the country, home to one of the most impressive collections of Impressionist art in the world.

Nearby, the Chicago Cultural Center is a stunning landmark filled with free exhibits, art, and performances. Gaze up at the largest Tiffany stained glass dome in the world while you’re there. And at Skydeck in Willis Tower (formerly Sears Tower), you can step out onto The Ledge — a glass box that extends outside the building, 1,353 feet up.

Last but not least, the Loop is where you’ll find Chicago’s celebrated Theatre District , buzzing with Tony Award-winning shows, world premieres, Broadway in Chicago, and glittering marquees at the likes of the Auditorium Theatre, the Cadillac Palace Theatre, and the Nederlander Theatre.

Chicago Greeter: free guided tours

Taste, shop and explore the neighborhoods with a friendly local as your guide. Explore rich histories, diverse cultural traditions and hidden treasures. See sides of the city you may not have adventured out to on your own, and take away a truly authentic Chicago experience. Greeter visits are customized based on your choice of neighborhoods, language and interests.

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39 Fun & Unusual Things to Do in Downtown Chicago, Illinois

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Thousands of tourists make their way to Chicago every year, and for good reason. The “windy city” has plenty to offer in the form of great architecture and a stunning skyline filled with skyscrapers, world-class museums, a growing craft beer culture, and a shoreline that mixes modern waterfront areas with miles of beaches and iconic landmarks.

From the legendary deep-dish pizza places to live blues performances in historic neighborhoods, the city resonates with a rich history and diverse cultural influences. The list of places to visit in Chicago is long and exciting and covers everything from amazing food to an exciting cultural scene.

No matter why you’re visiting, though, there are plenty of fun things to do in Chicago – so many, in fact, that we are focusing our list on the best things to do in Downtown Chicago , a 35-block area famous for its vibrant urban atmosphere.

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• Chicago tours

1 – Take a sightseeing river cruise

There’s no better way to admire the city’s great architecture than from the water – and the Chicago River offers the perfect opportunity to relax on board a cruise and enjoy Chicago’s iconic skyline.

Most cruises depart from Navy Pier and for 60-75 minutes (depending on which cruise you choose) will take you to see many of the city’s most famous landmarks, including the Tribune Tower, Marina City, and the John Hancock Center skyscraper.

You’ll sail under historical bridges, be able to listen to a live narration, and discover all three branches of the Chicago River as you learn about the buildings that helped shape the city.

Drinks are available for purchase and cruises depart several times a day, so you can choose the time more convenient for you.

• Boat cruises in Chicago

Read more about the best Chicago architecture boat tours

2 – Soak up some sun at Millennium Park

Covering almost 25 acres, Millenium Park is much more than just a green space in the heart of Chicago. Filled with interesting art and great attractions, the park has become a gathering point and the place to be for major annual events (like the lighting of the city’s Christmas tree every year).

Crown Fountain is perhaps the best-known spot in the park – a video tower sculpture that displays videos as it spouts waters into the reflecting pool next to it.

The park’s Jay Pritzker Pavilion, a massive outdoor amphitheater, is home to the Grant Park Symphony Orchestra and Chorus and holds musical series, summer concerts, and performing arts events.

Another favorite in the park is Cloud Gate (aka The Bean), a massive 10 m× 13 m×20 m stainless steel sculpture that reflects a distorted Chicago on every inch of its surface.

Near the northwest end of the park, there’s Wrigley Square, best known for its Millenium Monument, a fun semi-circle of 12-meter-tall Roman-style columns popular for photo opportunities and events.

3 – Get your culture fix at one of the many art museums in Chicago

Chicago is home to some incredible museums, and your list of things to do in Downtown Chicago should certainly include some of them.

With a world-class collection of over 300,000 pieces, The Art Institute of Chicago is a good place to start. If you’re still hungry for more great art, try the Museum of Contemporary Art , where the collection focuses on post-WWII artists.

With a massive collection of work by Ansel Adams, portraitist Julia Margaret Cameron, and street-photography pioneer Julia Margaret Cameron among many other famous names, the Museum of Contemporary Photography  is a great place to spend a couple of hours discovering the great American photographers of the past century.

Housed in a former private mansion, the Richard H. Driehaus Museum is an homage to the stunning decorative arts of the past two centuries. In addition to original art nouveau items, the home features lots of Tiffany glass and artworks and marble sculptures.

For a unique experience, it’s hard to beat the WNDR Museum , an immersive experience that features exhibits like an Infinity Mirror Room, audio-visual installations, and optical illusions.

Read more about the best museums in Chicago

4 – Enjoy the waterfront views at Navy Pier

The 1,000-meter-long pier has become one of Chicago’s most recognizable and popular destinations. Sitting right on Lake Michigan and home to a number of attractions, shops, and restaurants, the pier is a busy place no matter the season.

Outdoor attractions include everything from remote control boats to a drop tower, an old carousel, and a state-of-the-art Centennial Ferris Wheel that will take you over 60 meters up into the air for breathtaking 360-degree views over Chicago and Lake Michigan.

Other attractions include a 370-square-meter maze, a one-acre botanical garden, and the Chicago Children’s Museum. On rainy days, an IMAX theater and the Chicago Shakespeare Theater offer great indoor options as well.

Even if you don’t visit any of the attractions, the pier itself is a great place for a walk and often features outdoor art installations and live music in summer. The 45-meter Schooner Windy tall ship departs from Navy Pier and offers not only great views of the shoreline but also a choice of a Pirates-inspired sail or a sunset sail.

• Navy Pier Centennial Wheel tickets

5 – Say hi to marine creatures big and small at the Shedd Aquarium

Home to over 30,000 animals, the Shedd Aquarium is divided into major zones like Caribbean Reef, Amazon Rising, Polar Play Zone, and Waters of the World.

Learn about the animals inhabiting Chicago’s local waters, say hello to rescued green sea turtles, meet red-bellied piranhas and green anacondas, and pet giant rays. Or head to the underwater viewing area to come face to face with beluga whales, dolphins, and penguins.

A 4D theater inside the aquarium shows water-inspired films like Sea Monsters and Ice Age. There are also special temporary exhibits focused on beautiful marine creatures, the unique Australian Lungfish, sharks, and American alligators.

6 – Discover Chicago’s past with a gangsters and crime tour

The Windy City is historically known for being home to notorious mobsters during the 1920s Prohibition Era. Al Capone once called Chicago home and ran an underground gambling and bootlegging “industry” that was worth millions of dollars.

Today, plenty of tours will take you to the hot spots of Prohibition-era mobster activity, showing you the criminal underworld of Chicago and giving you a glimpse of how big names like Capone, the Untouchables, and John Dillinger forever changed the city.

Both walking and bus tours are available, and both come with a history-savvy guide who will take you to the most important location of Chicago’s criminal past. Visit the place where the St Valentine’s Day Massacre took place, stop by an old gangster headquarters, see where Al Capone used to carry out business and also where he went for fun, and stop by Harry Caray’s Italian Steakhouse to visit the secret vault once used by Frank Nitti.

Gangsters and Ghosts tours are also available, where you’ll get a peak into Chicago’s most haunted places, including the Palmer House and Death Alley.

• Gangsters and crime tours

7 – Take the kids to the Chicago Children’s Museum

At the top of things to do in Downtown Chigaco if you have kids is this interactive museum located at the popular Navy Pier. At almost 8,000 square meters, it’s one of the largest children’s museums in the country.

Four floors of hands-on exhibits are divided into three age groups, including babies and toddlers, ages 4-8, and ages 9 and up. This means everybody gets a chance to have fun learning for hours on end at the Chicago Children’s Museum .

Exhibits include everything from boats and climbing corners to an art studio, a kids’ town, a dinosaur area (complete with an excavation pit), and a tinkering lab where young scientists can explore technology, math, and engineering concepts.

8 – Catch breathtaking panoramic views from the 360 Chicago Observation Deck

There’s no better place to catch breathtaking 360-degree views of Chicago’s skyline than from the top of the 360 Chicago Observation Deck.

Set 94 stories up in the air, near the top of the John Hancock Center skyscraper, the observatory offers bird’s-eye views of many city landmarks as well as the lakefront shoreline and it’s definitely one of the best things to do in Downtown Chicago.

Just getting to the observatory is thrilling (you’ll be riding one of the fastest elevators in the country), but the real excitement here is TILT, a thrill ride in the form of a glass platform that tilts forward at a 30-degree angle so you can get the best downward-facing views from 1,000 meters up in the air.

The observatory is also home to the Architect’s Corner Café and Bar and an open-air SkyWalk.

• 360 Chicago Observation Deck tickets

9 – Discover local delicacies with a food tour

Chicago has its share of special local foods – perhaps the most famous ones being the Chicago deep-dish pizza or Chicago-style pizza and the iconic Italian beef sandwich – and the best way to experience them is through a food tour.

Stroll through the streets of Chicago with an expert guide and discover the best spots to taste a number of foods. Learn about the history of the city as you walk past famous landmarks like the Chicago River and Millennium Park and discover great architecture and street art.

Sink your teeth into some deep-dish pizza, sip a local beer, taste a Chicago-style hot dog, and enjoy original Italian pastries. You can even choose special food tours like a 2.5-hour Taste of Chinatown walking tour or a half-day tour exploring both the food and the architecture of Chicago.

• Food tours in Chicago

10 – See Chicago like never before from the Willis Tower Skydeck

The 108 stories tall Willis Tower is best known for its observatory. It’s not only the tallest Skydeck observatory in the country but also one of Chicago’s most popular attractions.

Here, visitors can step into retractable glass balconies – essentially glass boxes with a glass floor extending more than 1 meter out from the building.

Not only can you look 400 meters straight down over the streets below, but also get 360-degree views over Lake Michigan and spanning four states on clear, sunny days. Don’t miss out on this thrilling experience when in Chicago!

• Willis Tower Skydeck Chicago tickets

Hot tip: Cheap Skydeck Chicago Tickets – How to Save up to 20%

11 – See the city’s most famous buildings with an architecture tour

Chicago’s most iconic buildings sit near the river – and there’s no better way to enjoy them than with an architecture river cruise tour. Jump onboard and let your expert guide introduce you to landmark buildings as you cruise along all three branches of the Chicago River.

You’ll pass by the 36-floor neo-Gothic skyscraper Tribune Tower, the Rookery Building (Chicago’s oldest standing high-rise), and the Wrigley Building, a stunning 1920s skyscraper with a bright white facade. You’ll also see the Chicago Water Tower, listed on the National Register of Historic Places and once used to pump water from the lake.

Would you rather try an architectural walking tour of Chicago? For a shorter, self-guided architecture tour, head to the 2 km-long Chicago Riverwalk .

Otherwise, try The Loop route, which takes you through the best of Downtown Chicago art-deco buildings, where you’ll step inside the dazzling lobby of the Rookery Building, see the vibrant facade of the Chicago Board of Trade, and marvel at the beauty of buildings right out of the roaring 1920s.

Some of these walking tours will also take you to the Chicago Cultural Center (famous for its Tiffany glass dome) and the Chicago Architecture Center , where you’ll have a chance to learn more about the city’s architectural history.

• Architecture tours in Chicago

12 – Bite into the best of Chicago with sweet donut tours

Embark on an unusual journey through the Windy City with Downtown Chicago’s exclusive donut tour! This unique excursion takes enthusiasts on a flavorful adventure, stopping at some of the most renowned donut establishments in the heart of the Chicago Loop. Here, participants can indulge in a variety of donuts, from the classic glazed to rich cream-filled treats.

Are you vegan, on a gluten-free diet, or have a nut allergy? Don’t worry, your tour can be customized so you can enjoy lots of sweets without worrying about your diet. Along the way, a dedicated donut connoisseur will share fascinating details about Chicago’s rich donut history.

These two-hour walking tours aren’t just about trying lots of tasty donuts, though. Along the way, you’ll also have a chance to dive into the donut culture of Chicago and make memories one bite at a time!

• Donut tours in Chicago

13 – Visit the stunning Holy Name Cathedral

This breathtaking Gothic Revival cathedral was built after the Great Chicago Fire of 1871 destroyed two of the main churches in the city.

The result is an architectural marvel that mixes dark wood with lots of stained glass and details like massive bronze doors, 21-meter-tall ceilings, and a number of sculptures and castings depicting the apostles and Old Testament scenes.

The church is home to two pipe organs often used during mass and an overall design that focuses on the “Tree of Life” theme of Biblical salvation.

The Holy Name Cathedral is open to visitors during the day if you just want to admire its beauty and take some photos.

14 – Walk the historical Michigan Avenue

Running from the shore of Lake Michigan all the way through the city, Michigan Avenue was once primarily residential. Over the years, the road has been extended north of the Chicago River and now crosses over the Michigan Avenue Bridge (officially named the DuSable Bridge), connecting Chicago’s south side and north side.

Today, a walk down Michigan Avenue is one of the must-do things in Downtown Chicago. Home to some of the city’s most important attractions – including Millennium Park and The Art Institute of Chicago – Michigan Avenue has become an attraction in itself. Part of the reason for that is the stretch of the avenue known as the Magnificent Mile .

Flanked by skyscrapers and similar to Fifth Avenue in New York, the Magnificent Mile is filled with luxury shops, restaurants and 5-star hotels, and a number of Chicago landmarks. During the Christmas season, over a million lights are used to decorate the trees lining up the avenue.

• Walking tours in Chicago

15 – See the world’s largest dinosaur at the Field Museum of Natural History

With a collection of over 24 million objects, the Field Museum of Natural History (FMNH) is one of Chicago’s most impressive museums. The collection covers everything from fossils and meteorites to ancient civilizations, creepy creatures, gemstones, and biodiversity.

The main attractions here are, without a doubt, the dinosaurs – which include SUE (the most complete T.rex ever found) and Titanosaur Máximo, the largest dinosaur that ever lived at 37 meters long and almost 9 meters tall.

There’s also a 3D theater, a kid-friendly PlayLab, and an exciting Egyptian exhibit complete with mummies, a 4,000-year-old boat, and an ancient burial chamber.

The FMNH is part of the Museum Campus, a 57-acre waterfront park that’s also home to a number of other attractions such as the Adler Planetarium, the multi-purpose Soldier Field stadium, the Shedd Aquarium, and America’s largest convention space at McCormick Place.

• Field Museum of Natural History tickets

16 – Catch a game at the United Center

This multi-purpose indoor arena is the permanent home of the National Basketball Association’s Chicago Bulls and the National Hockey League’s Chicago Blackhawks. Other sporting events, including NCAA basketball, professional wrestling, and mixed martial arts tournaments are sometimes held at United Center as well.

With a capacity of over 20,000, the arena has also become a popular venue for concerts – over the years, everybody from Paul McCartney to Lady Gaga to the Rolling Stones has performed here.

The arena features a number of statues representing some of the most famous house players, including Michael Jordan and Blackhawks legend Bobby Hull.

If you’re visiting Chicago during the pre-season (which starts in October), you should be able to get tickets last minute to cheer for the local team.

• United Center tickets

17 – Discover the city with a hop-on hop-off bus tour

Save time and money and see all the city’s top sights with a hop-on hop-off bus tour. You’ll avoid headaches and trying to figure out an itinerary – just jump on board and get off at the stop of your choice to explore and take some photos.

When you’re ready, just get back on the open-top, double-decker bus and continue on your journey as you listen to the audio commentary and learn more about Chicago’s history and culture.

The bus takes you on a two-hour loop that includes 11 stops, such as the Navy Pier, the 360 Skydeck, Museum Campus, and the Chicago Riverwalk.

• Bus tours in Chicago

18 – Celebrate the world of sports at the Chicago Sports Museum

The 2100-square-foot Chicago Sports Museum not only houses a massive collection of sports memorabilia, but it’s also home to interactive experiences that will make you feel like your favorite sports stars are right there with you.

Learn about the evolution of baseballs, test your vertical jump against the giants of basketballs, see game memorabilia, and explore the history of Chicago baseball. You can jump into a racing car simulator and learn about the superstitions and legends of the sports world.

You can even see the original Sports Almanac prop from the movie “Back to the Future II,” which predicted the Chicago Cubs would win the World Series in 2015. The Cubs, which had not won a World Series since 1908, actually won the title in 2016 – just a year off from what the movie predicted.

19 – Trick your mind at the Museum of Illusions

Stop by this museum to discover a great collection of magic and trickery exhibits that will both confuse you and amuse you! Get ready for lots of interactive fun created with paint, holograms, and clever design.

Over 80 mind-bending illusions will keep both kids and adults busy for a couple of hours – Step into a spinning vortex tunnel, walk into rooms that defy the laws of physics and practice some anti-gravity moves, come face-to-face with a bottomless pit, and shrink yourself to tiny sizes.

You’ll find plenty of perfect selfie opportunities here; each exhibit even has a mark to show you where to stand for the best photos!

• Museum of Illusions tickets

20 – Take a segway tour around Grant Park

Looking for things to do in Downtown Chicago when you only have a couple of hours to fill? You can discover Chicago’s beautiful lakefront on a fun Segway tour as you learn about the area’s history and famous landmarks.

Most tours start at the Buckingham Fountain in Grant Park and then bring you closer to popular attractions like Lake Michigan and the city skyline, Museum Campus, and Millennium Park.

Don’t worry if this is your first time riding a Segway! Your tour guide will guide you through the basics before you set off on your adventure. There is nothing like seeing the city on a Segway tour – you’ll be able to cover a lot more ground than you would walking and have lots of fun in the process!

• Segway tours in Chicago

21 – Pedal past iconic landmarks on bike tours

Want to discover more of Downtown Chicago’s flavors and sights? You can choose from a long list of bike tours available to see a lot of downtown Chicago on two wheels. From the charming lakefront neighborhoods to the bustling heart of the city, there’s a journey for every explorer.

Foodies can choose a bike tour that allows them to sample the pillars of Chicago’s cuisine: deep-dish pizza, the famous Chicago hot dog, lush brownies, and locally crafted beers. Spanning roughly 13 miles, this ride provides a balanced mix of sightseeing and tasting the city’s favorite flavors.

If you would rather discover landmarks, choose a tour that takes you to the Windy City’s most famous sites, like the Buckingham Fountain’s mesmerizing light show, the Millennium Park, and the Museum Campus. Whether you’re exploring the city by day or ready to enjoy sunset time, Downtown Chicago’s bike tours guarantee an enriching and memorable experience.

• Bike tours in Chicago

22 – Spend an afternoon discovering Lincoln Park

Chicago’s largest park has so much to offer, you’d need an entire day to truly explore it all. Over 1,200 acres of green space serve as home to nature reserves, recreational facilities including a golf course and a skate park, and a number of public beaches that offer great swimming and boating facilities. North Avenue Beach is particularly popular and offers plenty of space for lounging shoreside and water activities.

Perhaps the most famous attraction here is the Lincoln Park Zoo , a 35-acre space home to over 1,000 animals. The Conservatory is another big draw, home to displays of everything from giant palms to an orchid room. The Peggy Notebaert Nature Museum is a nice complement, with a butterfly house and exhibits about the ecosystem of the region.

If you’re up for learning more about Chicago and American history, the Chicago History Museum offers a great look into the growth of the city, chronicles Lincoln’s assassination, and provides a number of exhibits for kids.

23 – Enjoy the magic of Lake Michigan

The largest (by area) of the five Great Lakes, Lake Michigan attracts thousands of visitors every year, who mostly come here for water sports like sea kayaking, kitesurfing, and yachting.

A number of wide and busy beaches line up the shoreline, with Ohio Street Beach offering convenience (it’s very close to Navy Pier) and lots of open space to lounge. Winter visitors often stop by the fascinating phenomenon of ice volcanoes forming on the lake.

Boat tours are a great way to discover the beauty of the lake. You can choose between a relaxing skyline or a brunch cruise. Or end the day with a relaxing dinner cruise where you can indulge both your eyes and your taste buds with a great all-you-can-eat buffet and onboard entertainment with DJ music.

Adrenaline lovers can choose an exciting speedboat ride that takes you on an architecture tour along skyscrapers and old bridges and ends with a massive fireworks display. There are also ferries that take passengers to different nearby islands for sunbathing in a bit more privacy.

If you’d rather stay on land, the 29km-long Lakefront Trail is a great way to explore the shoreline – no matter if you’re biking or hiking.

• Lake Michigan tours

24 – Get inspired at the American Writers Museum

The only museum in the country completely dedicated to American writers and their work, this quirky but interesting space offers exhibits on the work of novelists, poets, journalists, and even humor writers. There’s even a special section dedicated to the work of local Chicago writers.

Interactive stations allow visitors to play videos and sounds and even to activate scents connected to important literary works.

See how American writers from the 1600s and 1700s started to develop their own style away from European influence, what readers were choosing to read for fun through the centuries, and the writing habits of famous authors.

The American Writers Museum also hosts temporary exhibits and organizes special “meet the writers” evenings.

25 – Check out Soldier Field Stadium

The multi-purpose Soldier Field Stadium is home to the NFL’s Chicago Bears and the Chicago Fire FC soccer team, but it has also hosted a number of other events, including games for the Special Olympics, rallies from famous figures like Martin Luther King Jr, and the occasional hockey game.

The stadium can sit over 61,000 people, making it perfect for large events and shows. Concerts held here have included everybody from Barbra Streisand and Paul McCartney to The Rolling Stones, Madonna, and Jay-Z.

The 1924 stadium lost its National Historic Landmark designation in 2006 after an extensive renovation that modernized the space and added environmentally sustainable details.

• Soldier Field Stadium tickets

26 – Visit The Second City, Chicago’s best comedy club

If you’re looking for things to do in Downtown Chicago once the sun sets, this one is a must. Chicago’s oldest improv theater takes its name from one of the city’s old nicknames. Back in the early 20th century, Chicago earned the second-place slot in an ongoing rivalry between Chicago and NYC as the best metropolitan area.

While this might sound like a loss, Chicago has embraced its nickname in a fun way – and you can see just that when you visit The Second City premier comedy club.

The club served as the starting point for many famous comedians – including Alan Alda, Mike Myers, and Bill Murray – and a number of well-known performers still take to the stage here regularly. Stop by any night of the week for a laugh-out-loud good time with live shows starting at 7 pm.

27 – Defy gravity with indoor skydiving

Not ready to jump out of a plane? No worries — you can experience the exhilaration of skydiving without stepping foot on a plane! Your indoor skydiving adventure begins with comprehensive training so you can feel both prepared and confident for the flight ahead. Once ready, you will get your adrenaline pumping with two 60-second sessions of simulated free fall within a state-of-the-art vertical wind tunnel. It’s the true feeling of a skydiving adventure without the scary jumping!

Whether you’re a seasoned skydiver or a complete novice, indoor skydiving is lots of fun. During your flight, an instructor will be by your side, offering guidance and hands-on support for a smooth and thrilling experience. Dive into the skies of Chicago, even if they are simulated, and make memories that will last forever.

• Indoor skydiving in Chicago

28 – Spend the day at Maggie Daley Park

The 20-acre Maggie Daley Park , located near Lake Michigan, is best known for its many activities and features available.

The biggest attraction is the half km long ice skating ribbon, which runs along one side of the park and offers slight changes in elevation for some fun challenges. During the summer, the space is used as a rollerskating area.

Two rock-climbing structures with a maximum height of 12 meters welcome both beginners and experienced climbers and offer both bouldering and lead-harnessed climbing.

For family-friendly fun, there’s an 18-hole miniature golf course, tennis courts, and an Alice-in-Wonderland inspired “play garden” filled with lots of water features, climbing spaces, slides, and bridges for kids of all ages.

29 – Take a helicopter tour over Chicago’s skyline

Want to see Chicago’s beautiful architecture and green spaces from up above? A helicopter tour is the best way to do just that! Soar over Downtown Chicago, past the Willis Tower and over famous sights like Wrigley Field, the Navy Pier, and the Chicago River.

The 15-minute ride will allow you to capture stunning photos of the city in a Bell 206, turbine-engine helicopter. You’ll feel the rush of the flight combined with the excitement of seeing iconic landmarks like never before.

Private 45-minute scenic flights are a great choice if you’re traveling with your own group and want some privacy and out-of-this-world views of Chicago.

• Helicopter tours in Chicago

Read more about helicopter tours in Chicago – which one is the best?

30 – Attend a performance of the Chicago Symphony Orchestra at Orchestra Hall

The historical Orchestra Hall at the Symphony Center has been home to the Chicago Symphony Orchestra and the Chicago Symphony Chorus for many years.

While the building retains many original architectural details dating back to 1904, the Orchestra Hall was extensively renovated in the 20th century to improve acoustics, re-organize seating spaces to avoid blind spots, and add rehearsal spaces and features like a cafe and better lighting.

The hall’s concert series includes a mix of classical masterpieces and unique new shows, including piano concerts, kid-friendly programs, and acclaimed guest conductors. There are also unique movie experiences throughout the year where you get to enjoy classic films — from Amadeus to The Princess Bridge to Harry Potter — on giant screens as the orchestra performs the film’s score live.

• Chicago Symphony Orchestra tickets

31 – Grab a drink or two during a beer-tasting tour

Chicago has become a great destination for craft beer, and you can try several of them in one single evening when you book a special guided tour of some of the best breweries in town – you’ll get a chance to see the brewing process and enjoy plenty of beer samples along the way.

For a truly unique experience, grab a seat on the Chicago Craft Brewery Barrel bus tour. Visit a number of craft beer breweries onboard a bus shaped like a giant barrel reminiscent of those used during the 1920s Prohibition Era.

Want to explore on your own? There are plenty of breweries in Downtown Chicago that are worth a visit, including The Moody Tongue brewery with its barrel-aged brews, Motor Row Brewing and its unique beers (don’t miss their Blonde Belgian honey wheat brew), and Rock Bottom Restaurant & Brewery , one of the original breweries in Chicago.

Miller’s Pub , one of Chicago’s oldest late-night spots, offers great comfort food and an old-school vibe perfect for grabbing some drinks.

• Beer tasting in Chicago

32 – Scoop into sweetness at the Museum of Ice Cream

The Museum of Ice Cream is a unique, immersive experience that visitors of all ages can enjoy. Located in the heart of the city, this museum offers interactive installations, vibrant room designs, and, of course, a long list of ice cream flavors to savor.

Each room within the museum has been curated to offer a blend of art, sensory experiences, and the rich history of ice cream. Picture a forest of oversized ice cream cones, a sprinkle-filled swimming pool, and rooms dedicated to flavors from around the world. The Museum of Ice Cream is also an Instagrammer’s dream, with countless photo opportunities and fun backdrops.

For those who want a bit of history, the museum is also the perfect place to learn about the cultural and historical significance of ice cream and discover tidbits about its evolution over time.

• Museum of Ice Cream tickets

33 – Indulge your inner space explorer at the Adler Planetarium

Despite its name, the Adler Planetarium is also an astronomy and astrophysics museum. Built in the 1930s as the first planetarium in the country, the Adler has become synonymous with the quest for understanding the universe.

Visitors should stop at the planetarium’s Doane Observatory first, which is open on select Wednesdays nights, before heading into the main building to explore more. There, you can catch a show at the massive Grainger Sky Theater or the Samuel C. Johnson Family Star Theater, which specializes in 3D shows.

The museum includes a number of exhibits dedicated to the history of stargazing, the Chicago night sky, the missions to the moon (which includes the original Gemini 12 spacecraft), and our solar system.

Visitors can take photos with some of NASA’s rovers, learn through interactive stations, and take a look through a 17th-century telescope.

34 – Test your wits at The Escape Game Chicago

Do you have what it takes to find clues, solve puzzles and beat the clock? You have just 60 minutes to test your problem-solving skills and unlock the room – and you will require great teamwork and a sense of adventure to make it happen!

Rated the #1 Escape Room in the country with over 6,000 reviews on Google, The Escape Game Chicago offers five scenarios to choose from. Become a secret agent in a mission around a mysterious spice market, travel back in time to the Gold Rush era, fix your spaceship that just crash-landed on Mars, or find a stolen Monet painting.

Expert players can try their luck in the Prison Break room, considered one of the hardest escape rooms ever designed.

• Escape rooms in Chicago

Hot tip: Challenge your problem-solving skills at an escape room, highlighted as one of the best indoor activities in Chicago for groups

35 – Catch some late-night tunes at Buddy Guy’s Legends

Considered one of the best blues club in the country, Buddy Guy’s Legends prides itself for bringing the best blue acts and some of the world’s most talented musicians under one roof. Buddy Guy himself – a blues guitarist and singer who’s won eight Grammy Awards – performs at the club every January to a sold-out space.

Live shows are available seven nights a week but you can also stop by just to admire the amazing collection of personal items that cover the walls. From rare photos and artwork to Keith Richards and Eric Clapton’s personal guitars, there’s plenty to discover here.

36 – Grab a seat to the most exciting shows at the Chicago Theatre

The Chicago Theatre started life as an opulent movie theater in 1921 and is now considered one of the last surviving “grand movie palaces” in the country. The theater had space for a large live orchestra to accompany silent films, and an opulent interior that included stunning murals painted on the walls.

After years the neglect in the 1970s and a major restoration in the late 1980s, the Chicago Theatre now serves as a stage for everything from music concerts to comedy shows to stage plays.

Part of the restoration included revitalizing the theater’s interior and bringing back to life the grand lobby and staircase, Tiffany stained glass windows, and grand Wurlitzer pipe organ, one of the oldest of its kind still around.

• Chicago Theatre tickets & tours

37 – Connect with history at the International Museum of Surgical Science

Chicago’s most unique museum is home to a collection of items and exhibits focusing on the history of Eastern and Western medicine. From very early drawings and medical equipment to photographs, skeletons, and artifacts chronicling the breakthroughs and failures of medicine through the centuries, this is a museum that will awe, inspire and shock.

Special exhibits are dedicated to the 19th-century apothecary, polio and the use of the iron lung, pathology, the science of sight, and the history of dentistry.

The International Museum of Surgical Science also organizes temporary exhibits that focus on specific areas of medicine and history, such as a look into the deadly medicine of the Nazis, the world without polio, how the world has changed after 35 years of HIV/AIDS, and would healing through the ages.

38 – Catch a concert at the Civic Opera House

The country’s second-largest opera house, Civic Opera House , opened in 1929 and although it was extensively renovated in 1993, it still retains its original beauty. Limestone sculptures, gilt paint, and an opulent Art Deco lobby are still the heart of the building, where the traditional and the contemporary mix perfectly.

During the renovation, structural improvements and a state-of-the-art new sound system were added. Major operas like Madam Butterfly and La Boheme, as well as more modern options like Fiddler on the Roof now play here year-round.

• Civic Opera House tickets

39 – Let your imagination fly at the Briar Street Theatre’s Blue Man Show

Once a horse stable for the 19th-century Marshall Field department store, the space was abandoned and then used for several purposes until it reopened as the Briar Street Theater in 1985. With just 635 seats and an intimate elegant setup, this is a great space to truly appreciate a performance in the heart of Chicago.

While the theater still holds other performances (including full-length plays and musical shows) from time to time, it has mostly become known as the home of the performing Blue Man Group, where three characters painted in blue lead a multi-sensory experience combining music, theatrics, and visual effects.

• Blue Man Show tickets

How to get to Chicago?

A number of European airports (including Amsterdam, London, and Frankfurt) offer direct flights to Chicago’s O’Hare International Airport. From there, you can reach the heart of the city using airport shuttles and regional buses in about 40 minutes.

If you’re carrying a lot of luggage or arriving late and would rather go directly to your hotel, you have the option of using local taxi drivers, but be aware that extra fees might apply during busy hours or if you’re carrying lots of bags.

To save time and hassle, you can book an airport transfer . You won’t have to worry about timetables and you’ll arrive directly at your hotel’s door quickly and efficiently so you can make the most of your time in the city.

Where to stay in Downtown Chicago?

Sitting in a prime location overlooking the Chicago River, the Swissotel Chicago knows how to do luxury well. Expect sleek accommodations, a fitness center with panoramic views, and an award-winning restaurant. Plus, you’ll be within walking distance of all major Downtown Chicago attractions and steps away from Lake Michigan.

Just steps from Millennium Park, the Hampton Inn Majestic is a more affordable option with a great location in the theater district. It offers colorful, spacious rooms, and a 24/7 fitness center, and it’s surrounded by great restaurants and cafes.

Right on the Magnificent Mile, the 4-star Millennium Knickerbocker Chicago offers innovative design, well-appointed rooms, a ballroom with a gold-gilded domed ceiling, great farm-to-table cuisine, and a 1920s-inspired cocktail bar.

• best hotels in Downtown Chicago

Visiting Chicago on a budget?

Visiting Downtown Chicago on a budget doesn’t mean cutting corners on experiences. For example, many of the best tourist attractions in Chicago are either affordable or offer discounted rates.

Taking advantage of free walking tours in Chicago is another smart way to explore the city’s rich history and architectural marvels without breaking the bank.

Additionally, purchasing a  Chicago Go City Pass can grant you access to multiple attractions at a fraction of the individual costs, ensuring an economical yet memorable trip.

Final thoughts

We hope you’ve enjoyed our list of the best things to do in Downtown Chicago! With plenty of world-renowned cultural attractions, beautiful waterfronts with innovative architecture, and a past right out of a gangster movie, you won’t run out of exciting attractions here.

Have another favorite must-see attraction in Downtown Chicago to recommend? Let us know in the comments below.

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• Things to Do
• Food & Drink
• Time Out Market
• Attractions
• Los Angeles

The 63 best things to do in Chicago right now

Discover the best things to do in Chicago, from iconic venues and views to cultural musts and late-night shenanigans.

October 2024 : Fall  is here, and with it comes spooky season ! There's no shortage of great things to do, from  apple picking and pumpkin patches to haunted houses. And don't forget about the return of some of our favorite sports teams, either. There are plenty of other options, too, so stay satisfied and busy with these fun activities in October.

No matter where your interests lie, you can always find something to get excited about in this no-nonsense Midwestern metropolis. The best things to do in Chicago run the gamut—from seriously fun to awesomely educational. Looking for culture? Spend a day exploring Chicago museums . Hungry? You've come to the right place, because Chicago is famous for its delicious cuisine. There are tons of amazing restaurants in Chicago that highlight the city's rich and diverse culinary landscape. (And plenty of uniquely Chicago bars that do the trick, too.) We've searched all across the city to assemble this list of the best things to do in Chicago. Follow it and never get bored here again.

You can also find out more about how Time Out selects the very best things to do all over the world , or take a look at our list of the  best things to do in the world right now .

Been there, done that? Think again, my friend.

Time Out Market Chicago

We've rounded up the best chefs in the city to join us at Time Out Market Chicago, a culinary and cultural destination in the heart of Fulton Market featuring more than  15 kitchens, three bars and one drop-dead gorgeous rooftop terrace—all spread across three floors.

Best things to do in Chicago

1.  go apple picking at orchards near chicago.

• Things to do

What is it?  Plucking fruit straight from the source.

Why go? With a crisp chill in the air, fall is for picking pounds and pounds of apples to take home. The surrounding suburbs offer plenty of opportunities to do so, plus family-friendly activities and other delights like apple cider and apple cider donuts.

Don’t miss: A one-of-a-kind apple tree maze at Royal Oak Farm Orchard.

2.  Get frightened at a haunted house

What is it? Terrifying immersive attractions filled with monsters, clowns and other terrors that go bump in the night.

Why go? If you love to be scared, there’s no better time than fall. Plan a trip to the top haunted houses around Chicago and steel your nerves as grotesque horrors await in every room and dark corner.  

Don’t miss: Certain dates offer special experiences, like blackout nights or nights of isolation (no actors).

3.  Visit a pumpkin patch

What is it? Nearby destinations full of autumn festivities.

Why go? Nothing says fall like a pumpkin patch, where you pick out your own gourd, go on a hayride and play with animals in a petting zoo. Bring the whole family for an afternoon of fun; if you’re looking for even more seasonal activities, make a whole day out of it by going to the best places to see fall foliage outside of Chicago .

4.  Get lost in a corn maze

What is it? Intricately designed labyrinths set in large fields.

Why go? Whether it’s themed after Jurassic Park or Super Mario Bros., a corn maze offers excitement for both children and adults alike. Wander through acres of corn stalks, with mystery awaiting around every turn. Want to dial up the spookiness? One farm features a haunted corn maze that’s only open after dark.

5.  Admire autumn colors in city parks

What is it?   Every year, Chicago's trees burst into stunning shades of yellow, orange and crimson as fall descends upon the city for a few short weeks. 

Why go?  You'll see fall foliage whether you're looking for it or not—with trees scattered throughout the city, it's pretty hard to miss—but we prefer checking out some tried-and-true spots for maximizing gorgeous views. And between graceful weeping willows in Graceland Cemetery's arboretum, dense forest preserves and fiery red Japanese maples at the Chicago Botanic Garden, you're not short on options. 

Don't miss:   Peak fall color, thanks to this useful map that predicts when local foliage will achieve maximum splendor. 

6.  Catch a football game

What is it? Football season in Chicago.

Why go? With only a handful of home games each year, the opportunity to watch football live and in person is limited. That’s why weekends in the fall are often earmarked for gameday. Head to Soldier Field this season to tailgate and catch the Chicago Bears in action. For a unique experience, drive up to Evanston for a Northwestern Wildcats game in the team's temporary football stadium next to the lake.

Don’t miss: If you can’t make it to the stadium, the best sports bars in Chicago provide some pretty good seats and fan-filled atmospheres, too.

7.  Enjoy fall fun at Jack's Pumpkin Pop-Up

• River West/West Town Until Nov 3, 2024

What is it? A pumpkin patch pop-up in the middle of the city.

Why go? If you don’t have a car or simply don’t want to drive out to the suburbs, Jack’s Pumpkin Pop-Up is here to alleviate your FOMO by bringing fall fun to the city. Spread across a two-acre plot of land just west of Goose Island, the annual experience offers more than 10,000 pumpkins, a corn maze, axe throwing, carnival games, food trucks and much more.

8.  Have your mind blown at the Museum of Illusions

• Exhibitions
• price 2 of 4

What is it?  The Chicago outpost of a chain of trippy "edutainment" destinations, packed with mind-bending photo-ops.

Why go?  You'll be able to take a ton of cool Instagram photos at the Museum of Illusions, but you'll also have a chance to learn a thing or two along the way. Staff is present to explain the psychology and science behind each of the mind-bending displays.

Don't miss:  The museum's infinity room, which surrounds guests with mirrors and shimmering lights.

9.  Cheer on the Bulls and Blackhawks at the United Center

• Event spaces
• United Center

What is it?  Home to pro basketball and hockey, as well as big-ticket pop acts. 

Why go? You can't see Michael Jordan play at the United Center anymore (though you can get a picture in front of his statue in the venue's public atrium), but this West Side arena still hosts plenty of stars. During basketball and hockey season, the venue serves as home turf for the Bulls and the Blackhawks—two of the city's biggest pro sports teams. It's also a destination for major pop and rock concerts, including acts like U2, Drake and Madonna.

Don’t miss:  The arena has partnered with local restaurants like Honey Butter Fried Chicken and Lillie’s Q to provide dishes and drinks that handily outclass typical stadium fare.   

10.  Stroll along the Chicago Riverwalk

What is it? Expanded and updated in 2015, this riverside walkway hosts restaurants, bars, boating docks and plenty of spots to sit and admire the views.

Why go?  Like everything else downtown, the Riverwalk can be pricey, but you can't beat the views when you snag a glass of vino at City Winery or enjoy some local grub at Chicago Brewhouse. Several boat tour also have launch points along the Riverwalk, if you prefer to get out on the water.

Don't miss:  Post up at the Riverwalk nightly at 8:30pm and 9pm to catch Art on theMART, the 25-story light projection show across the water.

11.  Grab a paddle and glide along the Chicago River

• Sports and fitness
• Kayaking & canoeing
• River North

What is it? Kayak Chicago sends you paddling along the Chicago River from a dock located just north of Goose Island.

Why go? After a few quick lessons, you'll be ready to set out on a self-guided river tour in a kayak. You can rent your boat by the hour or pay a flat fee to take it out for the entire day and check out changing leaves along the water.

Don't miss: A handful of guided excursions that highlight Chicago architecture or simply allow you to navigate the river at night.

12.  Watch a movie at a rooftop theater

What is it?  Rooftop Cinema Club, an outdoor movie theater on the fifth floor terrace of the Emily Hotel.

Why go?  No other theater in Chicago can match the gorgeous cityscape views that accompany each screening here. The experience boasts state-of-the-art LED screens, wireless headphones for all guests, a range of seating options and a curated lineup of snacks and cocktails.

13.  Shop local at a farmers market

• Markets and fairs

What is it?  Weekly markets around town highlighting Midwest ingredients and products.

Why go?  You'll find the freshest, highest quality fruits, veggies, meats and more from local farms and businesses. There's also plenty of programming—from yoga to live music—and food vendors serving delicious bites for when you need to refuel.

14.  Travel across an elevated trail on the 606

• Parks and gardens
• Humboldt Park

What is it?  A formerly abandoned stretch of elevated railway track named after the first three digits in every Chicago zip code.  

Why go? Looking for a convenient way to get between Logan Square, Humboldt Park, Wicker Park and Bucktown? This is it. The 2.7-mile path was spruced up by the city and turned into a functional attraction that delights locals and visitors.

Don’t miss:  Local artist Jeff Zimmermann's colorful Conagra Mural (Urbs in Horto) just across the Milwaukee Avenue bridge, which acknowledges Chicago's agricultural legacy.

15.  Walk through a beautiful garden

What is it? The city’s lush green spaces, from Chicago parks to sprawling botanical gardens.

Why go? Get away from the bustle of the city and reconnect with nature by visiting one of these (mostly) free gardens. You’ll find stunning Japanese gardens, serene lily ponds, rose gardens, conservatories filled with thousands of plants, and much more.

16.  Go for a long run

What is it?  The best trails in the city and suburbs for runners.

Why go? Whether you're training for a marathon or just trying to get some excercise in, running outside sure beats the treadmill. From the 18-mile-long Lakefront Trail to the extensive North Branch Trail, there a host of places perfect for logging some serious miles.

17.  Bike to the ’burbs on the North Branch Trail

What is it?  A 16-mile paved trail beginning in Gompers Park that takes riders all the way to the Chicago Botanic Garden.

Why go?  If you're craving a quick escape from the city on your bike, you can take the North Branch Trail to attractions throughout the northern suburbs. Have a beer at Hubbard's Cave, get a pie at the Pequod's in Morton Grove or relax in the Erickson Woods in Winnetka.

Don't miss:  The four-mile loop trail through the Skokie Lagoons (which can also be used to get to the Chicago Botanic Garden).

18.  Bring your pup on a boat cruise

• Until Oct 13, 2024

What is it? A 90-minute, dog-friendly boat ride on the Chicago River and Lake Michigan.

Why go? Tired of the same old architectural cruise? Then liven things up with some pooches! Mercury Cruises offers a canine cruise every weekend, where you’ll be surrounded by four-legged friends as you take in unparalleled views of the skyline and learn about the city’s rich history. Plus there are plenty of photo ops, of course.

19.  Play pickleball

What is it? The fastest-growing sport in America.

Why play?  If you're looking for a new hobby or outdoor activity, why not take up a new sport? Requiring just two or four players, the game is easy to pick up and combines elements of tennis and badminton. There are numerous courts around the city (and more coming) so give it a try!

20.  Shop for wares at Maxwell Street Market

• Little Italy, UIC Until Oct 27, 2024

What is it?  A monthly flea market that dates back to the late 19th century.

Why go?  You can shop for just about everything imaginable, from furniture to clothes, household items, collectibles and more alongside live street performances and an abundance of delicious Mexican food.

21.  Hit the trails for a hike

What is it?  Hiking trails around Chicagoland.

Why go? Now that it's warm out, it's the perfect time to go hiking. Visit a state park or nature preserve for an adventurous escape from the city. These sprawling, winding paths will take you through historic sites, sand dunes, woodlands and much more.

22.  Watch the Chicago Symphony Orchestra in concert

• Classical and opera
• price 3 of 4

What is it?  A world-renowned orchestra.

Why go?:  Considered one of the leading and oldest orchestras in the United States, the CSO plays a variety of enthralling music and hosts touring soloists and small ensembles as well. You can also catch special performances set to the scores of popular films like Star Wars and Harry Potter. During fall to spring, Symphony Center is home to the CSO. 

Don't miss:  The 2024-25 season includes a celebration of the music from  Final Fantasy , led by legendary maestro Arnie Roth, on January 26.

23.  Show off your putt-putt skills at City Mini Golf

• Millennium Park

What is it? An 18-hole miniature golf course located in Maggie Daley Park.

Why go? There's a kitschy kind of charm to mini-golfing in the shadow of the Chicago skyline, especially since the course is decorated with replicas of famous Chicago attractions (like a six-foot-tall Willis Tower and a teeny version of the Picasso sculpture in Daley Plaza). 

Don’t miss:  Snapping a photo next to the mini Chicago landmark of your choice.

24.  Cruise around town on a Divvy e-bike

• Transport & Travel

What is it?  These jet-black e-bikes allow riders to go up to 15 miles per hour with the help of a small electric motor.

Why try it?  Let's face it: the original bright blue Divvy bikes are heavy and cumbersome. These newer e-bikes (which you'll find at stations throughout the city) make it easier to see more of the city atop a shared ride. The pedal-assist system adds some additional power everytime you move your legs, allowing you to get to your destination faster—and possibly without breaking a sweat.

Don't miss:  Divvy e-bikes come with an attached lock, meaning that you can end your ride by locking it to a bike rake or sign post, though you may incur an extra fee. You can also place them in any Divvy dock.

25.  Hop aboard Chicago’s First Lady for an architecture tour

What is it? The breeziest way to survey the city's famed architecture.

Why go? An architectural tour is a must for any visit to Chicago, and t he Chicago Architecture Foundation employs certified volunteer docents who narrate the history behind more than 50 downtown buildings for the duration of a 90-minute cruise along the Chicago River.

Don’t miss:  An evening version of the tour that allows you to take in the twinkling city lights from the river.

26.  Visit animals (for free!) at Lincoln Park Zoo

• Lincoln Park

What is it?  One of the last free zoos in the country, this 35-acre attraction connects visitors with animals from all over the world.

Why go? More than 1,000 critters are waiting for you to visit them—free of charge—in Lincoln Park.  From mammals (beavers, lions, otters and bears) to birds (penguins, eagles and parrots) to reptiles (snakes, crocodiles and turtles), there's something for every animal lover.  

Don’t miss:   The expansive Regenstein Macaque Forest, where snow monkeys swing from branch to branch. 

27.  See public art in Millennium Park

What is it?  The crown jewel of Chicago's front yard.

Why go?  Home to iconic public art installations such as   Cloud Gate   (a.k.a. "The Bean"), t his 25-acre park is one of the most popular gathering spots in the city . Visitors can walk through the vegetation in the Lurie Garden—renowned for its beauty throughout all of Chicago's seasons—or grab a requisite selfie in front of the Bean's reflective surface. 

Don’t miss:  Crown Fountain , an interactive installation featuring two 50-foot-tall LED video structures. 

28.  See Yoko Ono’s installation in Jackson Park

• Literary events

What is it?  Designed by activist and artist Yoko Ono, Skylanding is composed of 12 large steel lotus petals jutting from the ground of the Garden of the Phoenix in Jackson Park.

Why go?  Calling all public-art fanatics. This gleaming installation from the famed artist has become a major draw in the 600-acre park. The photogenic sculpture was erected as a symbol of peace, taking up residence on the site of a pavilion built by the Japanese government for the 1893 World’s Columbian Exposition .  

Don’t miss:  The park is also home to a beautiful, traditional Japanese respite dubbed the Garden of the Phoenix. 

29.  Hop aboard the Chicago Water Taxi

What is it?  For the first time since 2019, the Chicago Water Taxi is operating seven days a week.

Why go?  If you're looking to get out on the water for budget prices, you won’t find a better option than the bright yellow water taxi—a one-way ticket will set you back just $6, while 10-ride pass is $25.

30.  See live music at the iconic Morton Salt building

What is it?  The Salt Shed, Chicago’s new(ish) music venue from the team behind Thalia Hall and the Empty Bottle.

Why go?   Located at the site of the historic Morton Salt building (you know, the one you've probably spotted alongside the Kennedy Expressway), Salt Shed is an indoor/outdoor venue that's backed by a stellar sound system and skyline views during summertime performances.

Don’t miss:  Genuinely good concessions from notable Chicago restaurants.

31.  Eye masterpieces at the Art Institute of Chicago

• Art and design

What is it?  Guarded by an iconic pair of bronze lions, the Art Institute of Chicago houses a permanent collection of more than 300,000 artworks. 

Why go?   The Art Institute of Chicago is filled with masterpieces from every era, from Georges Seurat’s iconic painting   A Sunday on La Grande Jatte   (notable for its appearance in   Ferris Bueller’s Day Off ) to Andy Warhol's print of actress Elizabeth Taylor. This month, see Bruce Nauman's  Clown Torture , which chronicles the absurd misadventures of four clowns, each played by actor Walter Stevens.

Don’t miss:  Tucked away in the lower level of the Art Institute, the Thorne Miniature Room contains 68 recreations of American, European and Asian architecture and furniture, represented at 1:12 scale. It’s like a hyper-detailed, ultra-realistic doll house that you wish you had when you were a kid.

32.  Find serenity at the Garfield Park Conservatory

• East Garfield Park

What is it? A gorgeous glass structure home to more than 100,000 plants. 

Why go? When temps start to dip, there are few better places in Chicago to escape the cold than Garfield Park Conservatory, where you can wander through eight indoor display gardens full of greenery. Marvel at towering tropical plants in the 65-foot Palm House, admire cacti in the Desert House and imagine the primordial settings of Illinois millions of years ago among the lush Fern Room.   

Don't miss: Swing by Horticulture Hall from Friday through Sunday for a lavender oat milk cold brew made by Monday Coffee Co., the conservatory's resident coffee pop-up.

33.  Tap your toes to late-night jazz at the Green Mill

• Cocktail bars

What is it?  An Uptown institution that books smart bebop and free jazz with a discriminating ear. 

Why go?  In the ’20s, Chicago gangsters like Al Capone were known to frequent the Green Mill, but ever since Prohibition, the club has garnered a reputation for hosting live jazz every night. 

Don’t miss:  Taking a picture under the glittering marquee, which wasn't actually destroyed in Michael Mann's 1981 neo-noir film Thief . 

34.  See a blockbuster movie at Alamo Drafthouse

• Movie theaters
• Wrigleyville

What is it?  A popular movie theater chain from Texas.

Why go?  In addition to showing the latest films, the venue offers expansive food and beverage menus and servers will bring meals to customers' seats during screenings.

Don't miss:  The theater's special events, which include rowdy sceenings where talking is encouraged and movie parties—immersive and interactive viewing experiences featuring fun props, themed drinks and more.

35.  Go mini-golfing (and drinking) at Puttery

What is it?  A mini-golf cocktail bar.

Why go? If the weather outside isn't suitable for hitting the links, do the next best thing and go mini golfing at this unique concept. Housed in a 23,000-square-foot space, Puttery offers two themed courses and state-of-the-art technology like digital scorecards and trackable balls.

Don't miss: Take a load off after you're done playing by hanging out in the swanky lounge area. There's a a full menu of craft cocktails and approachable bites.

36.  Hang out with a mummy at the Field Museum

• Science and technology
• Museum Campus

What is it?  A massive natural history museum that was founded to house the biological and anthropological collections for the World’s Columbian Exposition of 1893. 

Why go?   With 350,000 square feet of permanent exhibitions to explore, deciding what to see at the Field Museum can be a daunting task. We recommend starting in the institution's popular "Inside Ancient Egypt" exhibit, where you'll descend into a recreation of the 5,000-year-old tomb of pharaoh’s son Unis-Ankh. From there, you'll walk through an extensive assemblage of Egyptian artifacts, including one of the largest collections of mummies in the U.S.

Don’t miss:  "Unseen Oceans," an exhibit dedicated to exploring the mysterious, rarely-seen world hidden underwater.

37.  See a stellar play from the Steppenwolf Theatre

What is it?  What people think of when they hear "Chicago theater."

Why go?  Steppenwolf is known for its all-star collection of ensemble talent (folks like Laurie Metcalf, John Malkovich and Tracy Letts number among its ranks).

Don't miss:   Noises Off,   a classic comedy that follows the cast and crew of a play within a play as they scramble to right the ship.

38.  Explore the universe at the Adler Planetarium

• price 1 of 4

What is it?:  A museum dedicated to astronomy and all things outer space.

Why go?:  You'll escape the planet with exhibits about the first lunar missions, the solar system and more, plus immersive shows in the dome theater. The Doane Observatory is also home to the largest public telescope in the area, and gathers 7,000 times more light than the human eye.

Don't miss: Adler at Night, the planetarium's afterhours event that takes place from 4pm-10pm every Wednesday. Best of all, entry is free for Illinois residents.

39.  Make a pit stop at the Chicago Cultural Center

What is it? Located just around the corner from Millennium Park, this gorgeous specimen of a building is the country's first free municipal cultural center; inside, you'll find tons of programming, exhibitions, and stunning architectural flourishes to explore, as well as a gift shop stocked with goods from local artists.

Why go? Anyone spending time in the Loop should make a point to check out any ongoing programming happening at the Cultural Center, which can run the gamut from art exhibitions to massive architectural expos. And did we mention it's completely free?

Don't miss: Once you've toured the 38-foot Tiffany glass dome in Preston Bradley Hall, head to the Landmarks Gallery  on the first floor to see "The Great Chicago Fire in Focus,"  an exhibit of images detailing the destruction of the historic disaster.

40.  Get acquainted with Frank Lloyd Wright’s architecture at the Robie House

• Historic buildings and sites

What is it?   A historic house that Wright himself called "the cornerstone of modern architecture." 

Why go?   Nearby Oak Park may be a mecca for Frank Lloyd Wright enthusiasts, but you can see some of the architect's finest work without leaving the city. The Robie House in Hyde Park exemplifies Wright's signature Prairie School style, both in its external appearance and interior design. You can take a peek inside the historic home (and get some decorating ideas) by taking a tour led by the Frank Lloyd Wright Trust, offered five days a week.

Don’t miss:  The bevy of beautiful art-glass windows and the furniture (also designed by Wright). 

41.  Go back in time at the Historic Pullman Foundation Exhibit Hall

What is it?  This destination  houses exhibits about the South Side 'hood's growth and preservation. 

Why go? When businessman George Pullman started a railroad sleeping car factory on the South Side of Chicago, he built an entire town to house his employees. The industrial complex has since been designated a National Park and the Pullman Exhibit Hall is the best place to start exploring the area.

Don’t miss:  Set out on a self-guided tour of the district, which includes historic buildings featured in films like  Road to Perdition  and  The Fugitive.

42.  Get high at 360 CHICAGO

• Streeterville

What is it?  Set atop the building formerly known as the John Hancock Center, this observatory offers views of the city (and surrounding states) from 1,030 feet above the streets.

Why go?  The sights from the 94th floor can't be beat, whether you're a longtime Chicagoan or a visitor. Stick around to enjoy a cocktail at 360 CHICAGO's bar or explore some of the interactive exhibits detailing the city's history.

Don't miss:  360 CHICAGO's most terrifying attraction: TILT. Guests board a glass-enclosed platform that slowly tilts over the side of the building at a 30-degree angle. Thrill seekers will want to fork over the additional fee for a ticket. 

43.  Catch rising bands at the Empty Bottle

• Rock and indie
• Ukrainian Village

What is it?  The best damn rock club in the States.

Why go? For more than a quarter of a century, a gig at the Empty Bottle has served as a rite of passage for local and touring musicians. The nondescript club on the edge of Ukrainian Village is far from the biggest venue in town (capacity is around 300), but the folks who book it have a knack for landing rockers, electronic acts and experimental musicians on the rise. Grab an Old Style, find a spot on the stairs by the stage and take in a sure-to-be memorable show. 

Don’t miss:  A slice of pizza before (or after) the show at next door's Pizza Friendly Pizza.  

44.  Take a stroll through Chinatown

• Public spaces
• Armour Square

What is it?   A neighborhood that serves as one of the primary hubs of Chicago's Chinese community, filled with restaurants, shops and incredible nods to East Asian architecture.

Why go?  Chinatown is a great place to mosey from shop to shop and spend some time outdoors, whether you're walking through Chinatown Square or admiring the sweeping skyline views from Ping Tom Memorial Park. 

Don't miss:   Dumplings from QYX, bubble tea from the walk-up window at Joy Yee, Peking duck from BBQ King House, cocktails at Nine Bar... the list goes on. Start at Chinatown Square and work your way south down Wentworth, passing under the street's famous gate and into its central commercial strip.

45.  Get down to house music at Smart Bar

What is it?  An ace place to lose it to house music, right in the city that invented the genre. 

Why go? In the ’80s, Chicago served as the epicenter of the creation of a new sound that still influences the work of modern hip-hop and electronic artists. If you want to experience house music, there's no more authentic environment than Smart Bar. Within the subterranean Wrigleyville club, skilled DJs, drag performers and sweaty revelers come together to the steady pulse of a house beat.

Don’t miss:   The crowded Queen dance party, which takes place nearly every Sunday night.

46.  Hear live blues at Kingston Mines

• Folk, country and blues
• Sheffield & DePaul

What is it? You have to listen to blues music when you’re in Chicago, and few places are as fun to see the blues as Kingston Mines.

Why go? The city’s largest and oldest continuously operating blues club features high-energy live blues bands performing on two stages until 4am Thursdays and Fridays and 5am on Saturdays. Whether you’re hanging with bleary-eyed tourists from Iowa or friends of the local blues guitarists on stage, it’s hard to have a bad time here.

Don’t miss: The cover grants you entry to both rooms and its two different stages.

47.  Sip suds at Half Acre Brewery Balmoral

• Lincoln Square

What is it? The far North Side warehouse where one of the city's largest breweries produces the majority of its beer.

Why go?  Half Acre Balmoral's expansive parking lot beer gaden offers room to sip signature brews like Daisy Cutter and Tome in the open air. Plus, a menu of bar foods is available for hungry drinkers. There's also an indoor taproom for the colder months. 

Don’t miss: There are beers on tap here that are exclusive to this location, so be on the lookout. 

48.  Walk through an outdoor art gallery at the 16th Street Murals

• Lower West Side

What is it? A collection of murals and street art on an old railroad embankment in Pilsen that stretches from the Chicago River to Western Avenue.

Why go?  Take a stroll across 16th Street and you'll spot murals by local artists like JC Rivera and Hebru Brantley as well as international talents like The Yok and Sheryo.

Don't miss:  An infamous painting of a severed possum by Belgian street artist ROA, located just west of 16th and Laflin Street.

49.  Tour the work of Ludwig Mies van der Rohe at the Illinois Institute of Technology

What is it?  The college's Bronzeville campus is studded with one of the country's largest collection of buildings designed by Ludwig Mies van der Rohe, the German-born steward of the Bauhaus architecture movement in Chicago. 

Why go?  Mies was a pioneering figure in American Modernism, and he completed some of his most significant work while serving as the director of the Department of Architecture at the Armour Institute of Technology. The sleek, column-free S.R. Crown Hall—which houses the present-day College of Architecture at IIT—is considered his masterpiece, and the college's entire campus has been inducted into the National Register of Historic Places. 

Don’t miss:  You can always take a self-guided tour, but the Chicago Architecture Center offers two-hour guided sessions that lead visitors through the evolution of the campus, from Mies' heyday in the mid-20th century to the more recent McCormick Tribune Campus Center designed by Pritzker Prize-winning Dutch architect Rem Koolhaas.

50.  Explore the gallery district on Chicago Avenue

• East Village

What is it?   A string of art galleries located on Chicago Avenue between Ashland Avenue and Wood Street. 

Why go?  A combination of favorable real estate, happenstance and collaborative spirit has drawn some of Chicago's finest galleries—including Matthew Rachman Gallery, DOCUMENT, Rhona Hoffman, Chicago Truborn and many others—to this multi-block stretch in West Town, creating a concentrated (and not to mention, free) tour of curated work. Plan an afternoon around the exhibitions that pique your interest, and don't forget to make a reservation at each gallery ahead of time. 

Don’t miss:  Looking to splurge on, say, a mid-century Danish sofa or a luxury cowhide rug? Make an appointment at Matthew Rachman Gallery to view the furniture collection available for sale, where you'll find items from iconic designers like Vladimir Kagan, Jens Risom and Eero Saarinen.  

51.  Watch fish swim by at Shedd Aquarium

• Zoo and aquariums

What is it?  Chicago's only aquarium, home to thousands of colorful fish and other aquatic creatures.

Why go?   Permanent exhibitions like "Wild Reef" and "Amazon" allow you to gaze at fish, stingrays, an anaconda and sharks. But the interactive experiences may be the biggest draw, allowing visitors to get up close and personal with some of the animals that live at the Shedd Aquarium and learn more about them.

Don't miss:  The internet-famous rockhopper penguins, known for exploring the Shedd (and other Chicago institutions) during lockdown in 2020. You can say hi to them in the Polar Play Zone exhibit.

52.  Take in the skyline from Promontory Point

What is it? One of the best places to sit on a rock and look at tall buildings from afar.

Why go? Just north of the Museum of Science and Industry, this man-made peninsula is a short jaunt from the Lakefront Trail. When the sun is out, it's a beloved spot for picnics, lounging and canoodling on the rock steps that line the perimeter of the point.

Don’t miss: The Promontory Point Field House, an extremely popular wedding venue that looks like a miniature castle.

53.  Have your mind blown at the Chicago Magic Lounge

What is it? A love letter to all things magic hidden behind what  appears to be a laundromat.

Why go? After three years of performances at Uptown Underground , the Chicago Magic Lounge’s brick-and-mortar manifestation opened in early 2018. The spot sports three performance spaces. There’s the front bar, where you can enjoy a drink and some sleight-of-hand. Then there’s the 120-seat Blackstone Cabaret mainstage, where ticketed shows take place, as well as a smaller back room, dubbed the 654 Club, offers up-close magic. Don’t miss: While enjoying your cocktail in the bar, check out the magician’s table built into the center of the bar itself. 

54.  Watch 30 plays in 60 minutes at the Neo-Futurarium

• Interactive

What is it? A theater where performance art is populist and fun AF. 

Why go?  You never know what you'll see when you attend the Neo-Futurists' signature show,  Infinite Wrench , but it's nearly always entertaining. The ensemble races against the clock to cram 30 miniature, two-minute plays into a 60-minute show that bristles with madcap energy. Over the course of the evening, you might witness a dramatic monologue, a funny song or simply stare at someone eating a sandwich. 

Don’t miss:  Grab a seat toward the front of the stage if you're game for interacting directly with the show's performers (their plays occasionally call for audience participation). 

55.  Double over laughing at the Second City

• Comedy clubs

What is it?  Where Bill Murray,  Tina Fey, Gilda Radner, Chris Farley and Steve Carell  cut their comedic teeth. 

Why go?   Before they joined the cast of   Saturday Night Live   or became big-screen stars, those folks above practiced their craft on the mainstage at the Second City. The venue's premiere revue features some of the institution's most talented performers in a series of loosely-connected, topical comedy sketches.

56.  Drink all the brews at the Beer Temple

• Liquor stores

What is it?  A place of worship for hops-heads.

Why go? You'll always find something new or unexpected on tap at this Avondale bar and bottle shop, which has gained a reputation for stocking the most sought-after releases from local and out-of-state brewers. 

Don’t miss:  Follow the Beer Temple on Instagram to stay on top of what's newly in-stock. If you want to get your hands on the latest brews from Hop Butcher and other hard-to-find releases, you'll need to order quickly.

57.  Take a ride on Navy Pier's Centennial Wheel

• Towers and viewpoints

What is it? : A nearly 200-foot-high Ferris wheel.

Why go?:  You won't find many sights that can rival the ones from Centennial Wheel. Riders are treated to 360-degree views of the skyline and Lake Michigan while sitting in enclosed, climate-controlled gondolas.

Don't miss:  After your ride, head to the Original Rainbow Cone at Navy Pier for a tasty sweet treat.

58.  Find something strange at Woolly Mammoth Antiques & Oddities

What is it?  A store that's not for the faint of heart and is one hell of a conversation starter.

Why go? You never know what you'll find at this popular Andersonville antique store, which prides itself on stocking items that are "resurrected from the past." Taxidermy, diving helmets, military supplies and other interesting knick-knacks typically line the shelves.

Don’t miss:  The anatomy items, medical stuff, skull bones (of all kinds) and skeletons.

59.  Add to your reading list at Pilsen Community Books

What is it?  A worker-owned bookstore, offering new and used books for in-store browsing and curbside pickup.

Why go?  You can support a local business while chipping away at your reading list by ordering something from this Pilsen shop. Submit an order online or call and talk to a human during business hours if you need a recommendation.

Don't miss:  Add a donation to the Liberation Library to your order to support the purchase of books for incarcerated youth.

60.  Explore cinematic history at Doc Films

• Independent

What is it? The University of Chicago's single-screen theater is the longest continuously running student film society in the country.

Why go? In the fall, winter and spring, this Hyde Park institution sheds light on some of the most obscure corners of film history, showcasing retrospectives of underappreciated directors, deep dives into highly specific movie genres and rarely-screened foreign films. Best of all, a ticket will only set you back $7.

Don't miss: Prefer to see something contemporary on the big screen? Stop by on Saturday nights, which are typically reserved for screenings of new and recent releases.

61.  Find some new records at Dusty Groove

• Music and entertainment

What is it?  A Wicker Park destination for discerning record nerds.

Why go? The "dusty grooves" of course refer to the wonderous global rhythms found in the smartly curated bins, sorted into Tropicalia, Afrobeat, reggae, vintage soul, French pop, blues, jazz and other genres. 

Don’t miss:  Obscure titles that you'll have a hard time finding elsewhere in the city.

62.  Watch a movie at the Music Box Theatre

What is it?  Chicago's premiere arthouse theater. 

Why go? Aside from being one of the 50 most beautiful cinemas in the world , the Music Box's screens one of the best assortments of arthouse films, documentaries and foreign language pictures in the city. And if you prefer to turn your living room into a theater,  Music Box Direct allows you to stream movies at home.

Don't miss:  Performances on the theatre organ, which is played during weekend intermissions, monthly silent film screenings and other special presentations. 

63.  Set a high score at Logan Arcade

• Logan Square

What is it? An expansive, bar-equipped arcade housed inside a former hardware store.

Why go? There are many arcade bars scattered throughout Chicago, but Logan Arcade boasts one of the largest (and best maintained) collection of games. You'll find classics like Ms. Pac-Man and Q*Bert alongside more modern machines like Mario Kart and a Jurassic Park shooter. Pinball wizards will flip over the selection of tables, including ones inspired by properties like Game of Thrones and Star Wars . Plus, you can sip a craft beer or cocktail between high-score attempts.

Don't miss: The Killer Queen cabinet, which allows two teams of five players to face off in a bee-themed battle that requires some intense cooperation to achieve victory.

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