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Inside Chicago Walking Tours

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“ Five friends came with me today on a private 2-hr tour of a slice of Chicago with Hillary from Inside Chicago. ” in 42 reviews

“ It's always a joy to be around others like Adam that take pride and enjoy the history of Chicago. ” in 12 reviews

“ A friend and I joined the Secrets of the Loop tour , and we very much enjoyed our experience. ” in 3 reviews

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Top-rated architecture walking tours of downtown Chicago and neighborhoods. Woman-owned small business. Highly engaging, expert historians and local comedians on staff. …

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We did the Words Within tour with Adam as our tour guide. He was very knowledgeable and energetic! Would do another Inside Chicago Walking tour again! Thanks, Adam!

As the tour guide, Kylie was very knowledgeable and, most importantly, a great and pleasing personality that made the tour educational and pleasant despite the biting cold! (We're from California!) Also, we were running late because of the Chicago BOA Marathon, but Hillary from the tour office ensured we did not miss our tour. She and Kylie coordinated so we could still join the tour despite being 20 minutes behind.

Kylie, as a tour guide, is animated but loud and clear in her delivery.

RO -- for Ron Ordona?

Our tour guide Kaylee was great! Very knowledgeable and enthusiastic. Learned a lot about the pedways!

Colleen was a polished guide! We also loved Hilary the previous day on the Tours & Boats "Chicago's Best 90-Min Architecture Boat Tour on The Chicago River."

Spent the two hours pedway walking tour with Adam. He was very knowledgeable and energetic and was a delight of a tour guide. We are native chicagoans and we learned many things we did not know. It's always a joy to be around others like Adam that take pride and enjoy the history of Chicago. Would recommend 10/10

I joined four others for a tour of the Chicago Pedway with Colleen. It was delightful - informative and fun. Colleen was great - friendly with a font of information about the city and architecture.

Colleen our tour guide did great and is an Improv comedian. Very knowledgeable and fun.

Spent the day on TWO tours with Hailey. Interiors and Pedgo and would 10/10 recommend this experience! We did the boat tour with Hillary earlier in the weekend and enjoyed that as well. Overall, a great experience and way to learn about Chicago!

We walked "The Underground Pedway and Secrets of the Loop" with Hillary. The tour was informative and interesting, and definitely found interesting places we never would have found on our own. She also pointed out a bunch of architectural details (and even an entire building!) that we would have missed seeing even if we had gone by them on our own.

An informative tour that is well worth the ticket price. Kylie was our tour guide and she was knowledgeable and very considerate of all the guests. About 12 guests on our tour which was a nice size. Wear comfortable shoes - you'll walk several miles.

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Inside chicago walking tours.

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• www.insidechicagowalkingtours.com
• (312) 799-0164
• Women Owned

TripAdvisor’s TOP-RANKED walking tour company in Chicago (out of 400+), offering interior-focused architecture tours that delight visitors with the “second side of the Second City,” with gorgeous, fascinating, and often hidden details behind many doors.

Inside Chicago Walking Tours is a woman-owned small business founded by Hillary Marzec, an experienced tour guide and product development director for a major sightseeing company in Chicago. Given the freedom to research and construct her own tours, she used her years of experience as a teacher, writer, improv comedian, and tour guide to create tours that tell the story of Chicago in an engaging, educational, and always entertaining way.

What makes us different? It’s our ability to find the hidden and fascinating details of buildings and areas that people pass through or pass by every day. It’s our passion for showing visitors, whether they be out-of-towners or Chicagoans, a side of Chicago that they haven’t noticed before. We love to focus on the stunning interiors of buildings throughout downtown Chicago – including many of the buildings along the river – and we even provide you with an “insider’s scoop” on lots of the exterior architectural elements that most guides won’t show you.

General Information:

• Tours average 2 hours, and cover 1.5 miles at a leisurely pace; • Rotating list of tour routes each season, covering everything from architecture to history, science, folklore, and more; • Great for all ages, and very family-friendly; • 20% off your tickets with promo code “CHOOSE” (for Choose Chicago); • Public tours and private tours available year-round!

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Average Visit/Tour Length 2 hours (1.5 miles)

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Miles from O'Hare Airport 16.0

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Summertime doesn’t have to mean taking a break from learning. Here are some of the best walking tours for taking in Chicago history, including a jaunt from the Chicago Workers Cottage Initiative.

Courtesy of Tom Vlodek/Chicago Workers Cottage Initiative

These five Chicago history tours will show you a different slice of the city

This summer, brush up on your local history with tours that highlight everything from architectural styles to underground critters..

In a city with a history as rich as Chicago’s, summertime doesn’t always have to mean taking a break from learning.

Whether you want to explore outside your neighborhood, fire up your kids’ summer brains or simply try something different, this list presents you with options.

• The wilds of Chicago: 10 places to bask in nature without leaving home

Head underground … and watch for rats

Why go on a walking tour that openly plugs rats? Because those critters own this city just as much as we do. For proof — and to earn a new appreciation for our fellow citydwellers — sign up for local tour guide Mike McMains’s “ Underground Chicago (Plus Rats!) Tour ”: a 90-minute exploration of the city under the city. Departing from the Mag Mile and quickly descending into the lower regions and underbelly of the city, it’s an educational way to learn something new about Chicago, entertain guests hankering for a tour or simply avoid the hot summer sun. $30, 90 minutes. Next tour is July 6.

The Jaffee History Trail features eight informative stops with facts about the city’s history.

Courtesy of the Chicago History Museum

Stroll the Jaffee History Trail

If you haven’t taken the time to explore the Jaffee History Trail , which opened in 2021 just east of the Chicago History Museum, put it on your list this summer. Encompassing 4.5 acres of landscaped grounds planted with native pollinators, the little trail features eight informative stops with representations of the city’s history — from the giant hunk of metal discovered in the museum’s back yard to the infamous Couch Tomb. Free; explore at your own pace. Daily.

Chicago historian Shermann “Dilla” Thomas speaks to local high schoolers playing in the Double Duty Classic baseball game during a bus tour in 2023 in Chicago.

Owen Ziliak/Chicago Sun-Times

Take a bus tour with Dilla

Most locals know Auburn Gresham–based historian Sherman “Dilla” Thomas from his viral TikTok videos proving “everything dope about America comes from Chicago.” But have you ever taken one of his neighborhood tours ? Book tickets and board the bus for one of Dilla’s Mahogany Tours through neighborhoods on the South and West sides such as North Lawndale, Englewood or Bronzeville. $45, durations vary. Weekends.

The Chicago Workers Cottage Initiative leads informative tours of cottage-heavy neighborhoods such as McKinley Park and Logan Square.

Learn about a seminal architectural style

If you pay any attention to residential buildings in older parts of town, you may be familiar with the typical workers cottage: small, 1 1/2-story homes built for working-class families between the 1880s and 1919. Across the city, there are nearly 60,000 of these homes, but they’re rapidly being demolished. Enter the Chicago Workers Cottage Initiative : a small group of people who organized themselves in 2021 to celebrate these little houses in attempts to preserve them from demolition. During the warmer months, the group occasionally leads informative, intimate tours of workers cottage-heavy neighborhoods such as McKinley Park and Logan Square. Donation, 90 minutes. Weekends.

This photo shows an aerial view after the first atomic explosion at the Trinity Test Site near Alamogordo, N.M., on July 16, 1945. Trinity Site, a designated National Historic Landmark, only opens to the public twice a year. But the UChicago campus also played a vital role, and visitors can walk a historical route there nearly any day of the year.

AP Photo, File

Dig into the city’s love affair with film

Yes, we know about the Art Institute’s Ferris Bueller’s Day Off tour — but this one’s better. “ From Fairgrounds to Film Set: Chicago’s Midway, Movies, and the 1893 World’s Fair ” starts from the Midway Plaisance, whose ties go back to the World’s Fair, then winds along the tree-lined streets of Hyde Park to showcase five stops tied to the movies. It’s worth your time just to stroll through the leafy University of Chicago campus, and you’ll walk away with a new appreciation for our city’s role in the film industry. $29.99, 75 minutes. Next tour is June 30.

Want to take your own film-related tour? Stream the Oscar-winning movie Oppenheimer, then take this self-led, WBEZ created tour of the relevant atomic sites on the campus of the University of Chicago.

Lauren Viera has covered Chicago’s arts and cultural scenes for more than 20 years. She is the author of The 500 Hidden Secrets of Chicago (Luster) and lives in Logan Square.

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Walking tour highlights Chicago's LGBTQ+ history

W alking and trolley tours offer Chicagoans an opportunity to learn more about LGBTQ+ history in the Loop, the North Side and the South Side.

Why it matters: LGBTQ+ people don't always get proper recognition because so many of their stories have been ignored or stifled. The tours celebrate how integral LGBTQ+ people were —and are — in politics, publishing, architecture, the military and business.

Driving the news: Mike McMains, the one-man operation behind Tours with Mike , leads the tours, which connect buildings and locations to LGBTQ+ people and moments in history.

How it works: The downtown tour meets at Ida B. Wells and State Street where guests scan a QR code that offers more details and visuals for each stop along the tour.

• The walking tour (at $30 per person) is about one mile and takes two hours.

The big picture: This is the second year McMains has offered the LGBTQ+ -focused tours for Pride month, and he purposefully included downtown and the South Side, where the history isn't discussed as often as it is in neighborhoods like Northalsted.

• McMains also offers private tours, which can be LGBTQ+-themed, throughout the year.

Between the lines: McMains shares anecdotes on the tour suggesting some figures from the 19th century into the 21st century may have been gay or transgender even if they didn't publicly identify as such because of long-held hostility toward the LGBTQ+ community.

Louis Sullivan's Auditorium Theatre. Photo: Carrie Shepherd/Axios

Case in point: Louis Sullivan, "Father of the Skyscraper" and mentor to Frank Lloyd Wright, is featured during a stop by Sullivan's Auditorium Theatre.

• McMains shares what ostensibly is a love letter from Sullivan to Walt Whitman and points out the architect's preference for visiting men's clubs.

Zoom in: Some spots along the downtown route include modern LGBTQ+ power players like Chuck Renslow, founder of International Mr. Leather, and Lena Waithe, a Columbia College graduate.

What they're saying: " There are so many contributions that LGBTQ people have had all over the city, and I hope that people are just encouraged to try to learn more and to see these are really amazing stories that people have not heard of," McMains tells Axios.

If you go: Tickets must be reserved in advance.

• Tickets are still available (at $40 per person) for the June 22 South Side trolley tours, departing from Millennium Park at 10am and 1pm.
• Downtown and North Side walking tours are also offered this month .

The bottom line: I learned so much about a part of Chicago history I thought I really knew. I was especially touched by the story of a transgender soldier from the Civil War.

Get the rundown of the biggest stories of the day with Axios Daily Essentials.

John Early Announces Tour and ‘Now More Than Ever’ Album With Bonus Madonna, Aaliyah Covers (EXCLUSIVE)

By Ethan Shanfeld

Ethan Shanfeld

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You’ll soon be able to listen to John Early ‘s covers of Britney Spears’ “Overprotected” and Neil Young’s “After the Gold Rush” on vinyl.

On Sept. 13, the alt-comedy icon will release an album for his 2023 HBO comedy special “Now More Than Ever,” featuring bits on Apple’s “ask app not to track” button, the emptiness of millennial culture and anal sex — as well as cover songs performed with his fictional band the Lemon Squares. Available on digital, vinyl and CD, it will also feature an exclusive, album-only set from Early’s denim-loving alter-ego, Vicky With a “V.”

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Early is also launching a North American fall tour kicking off Sept. 9 in San Diego. It will end Oct. 21 in Durham, N.C., and pass through Los Angeles, San Francisco, Boston, Chicago, New York and other American cities (plus Toronto). Early will be flanked by the whole band in L.A. and New York, and bandleader Hesslein on the rest of the dates.

“I’ve been performing comedy and music with my long suffering band the Lemon Squares for over 10 years now, and I always assumed that there was no way to capture the magic of our live shows,” Early said in a statement. “But listening to this album takes me right back to that sweaty night in downtown Brooklyn, which felt something like being a crazed preacher at a tent revival. I’m so excited for people to hear the Vicky With a ‘V’ set that we had to cut from the HBO special for time. And I am so, so pumped about our new cover songs which I think are genuinely good and stanky. I would also like to put it on permanent record that I did the Madonna rap in one take.”

Purchase tickets to Early’s tour on Friday, June 14, at 10 a.m. local time here . Dates below:

Mon. Sept. 9 – San Diego, CA @ The Casbah Tue. Sept. 10 – Seattle, WA @ The Showbox Thu. Sept. 12 – Portland, OR @ Revolution Hall Fri. Sept. 13 – San Francisco, CA @ Bimbo’s 365 Club Tue. Sept. 17 – Los Angeles, CA @ Teragram Ballroom Wed. Sept. 18 – Phoenix, AZ @ The Crescent Ballroom Fri. Sept. 20 – Dallas, TX @ Club Dada Sat. Sept. 21 – Austin, TX @ Mohawk Wed. Oct. 2 – Cleveland, OH @ Grog Shop Thu. Oct. 3 – Toronto, ON @ The Opera House Fri. Oct. 4 – Ann Arbor, MI @ Blind Pig Sat. Oct. 5 – Chicago, IL @ Thalia Hall Sun. Oct. 6 – Madison, WI @ Majestic Theatre Mon. Oct. 7 – Minneapolis, MN @ The Fine Line Sun. Oct. 13 – Philadelphia, PA @ Underground Arts Mon. Oct. 14 – New York, NY @ Webster Hall Tue. Oct. 15 – Boston, MA @ The Wilbur Wed. Oct. 16 – Washington, DC @ Black Cat Sat. Oct. 19 – Nashville, TN @ The Basement East Sun. Oct. 20 – Atlanta, GA @ The Earl Mon. Oct. 21 – Durham, NC @ Motorco Music Hall

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