On foot · CHICAGO WALKING TOURS

15 Chicago Walking Tours Worth Booking

27 walks  ·  from $32 a head

The 15 best chicago walking tours you can book today, with what each costs, how long it runs and how far it actually walks. Number one is there for a reason.

Chicago: Gangsters and Ghosts Walking Tour - Millennium Park and the famous Bean
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Chicago: Gangsters and Ghosts Walking Tour

1.Gangsters and Ghosts Walking Tour

★★★★★★★★★★5.0 · 7,155 reviews · from $52Our pick

Walk about 1.5 miles through Chicago’s Loop with a historian guide, hearing true stories of Al Capone, bootleggers, tragic accidents, and reported ghosts. Stops include Millennium Park, the Palmer House, the Riverwalk, the Chicago Theatre, and Congress Plaza Hotel. A minibus option is also available.

“Taka was our guide and she was fantastic! The stories were interesting, her directions were clear, she kept the group on time, and she projected her voice and spoke very clearly in a large group on loud city streets. We would definitely recommend this tour!”

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Chicago Favorites Ultimate Food and Walking Tour - Starting with deep dish at Lou Malnati’s or Gino’s East
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Chicago Favorites Ultimate Food and Walking Tour

2.Chicago Favorites Ultimate Food and Walking Tour

★★★★★★★★★★5.0 · 1,962 reviews · 3 hours (approx.) · from $84

Walk about 1.5 miles through downtown Chicago while sampling deep-dish pizza, a hot dog, Italian beef, Garrett’s popcorn, and a brownie or gelato. Guides such as Gabe, Fran, Jessika, and Kevin add architecture and local stories. A two-hour bike or kayak rental is included.

“It wss a great experience. MJ knows his stuff. The food is good at nice places. It was better than expected.”

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Chicago: Gangsters and Ghosts Guided Walking Tour - Death Alley and the riverfront’s ghost stories
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Chicago: Gangsters and Ghosts Guided Walking Tour

3.Gangsters and Ghosts Guided Walking Tour

★★★★★★★★★★4.7 · 1,697 reviews · 2 hours · from $36

Walk about 1.5 miles through Chicago’s South Loop with an English-speaking historian guide. Hear stories of Al Capone, secret tunnels, Death Alley, and haunted landmarks, then visit the Palmer House and Congress Hotel. Guides such as Max, Baylor, Tanner, and Sophia are known for lively storytelling.

“Our tour was really good, I really enjoyed the stories and I saw bits of the city I wouldn’t maybe have gone to otherwise. Our guide Thalia was really knowledgeable, I had lots of questions, and delivered the stories in a funny and engaging way”

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Chicago Loop District Food Tour with Deep Dish & Beef Sandwich - Starting at the Chicago Public Library’s Hall Branch
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Chicago Loop District Food Tour with Deep Dish & Beef Sandwich

4.Chicago Loop District Food Tour with Deep Dish & Beef Sandwich

★★★★★★★★★★5.0 · 870 reviews · 3 hours (approx.) · from $84

Walk Chicago’s Loop with a local foodie guide, tasting sausage deep dish, Italian beef, a hot dog, popcorn, brownie, churro, and a secret dish. You’ll see Willis Tower, the Rookery, Calder’s Flamingo, and Millennium Park. Guides such as Danny, Eliot, Lance, and Mike are praised for lively city stories.

“Make sure you are hungry when you arrive because there is a ton of food! The whole experience was 5 star. Lots of history mixed with great cuisine. Eliot was easy going and made the tour fun!”

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Chicago's Secret Interiors Architectural Walking Tour - La Salle Street and Chicago’s Financial Canyon
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Chicago’s Secret Interiors Architectural Walking Tour

5.Chicago’s Secret Interiors Architectural Walking Tour

★★★★★★★★★★5.0 · 635 reviews · from $35

Walk from Union Station through Chicago’s Loop with guides such as Ethan, Grant, Ty, and Matthew. Expect grand lobbies, mosaics, domes, Beaux-Arts hotels, and stories of Gilded Age tycoons. The route ends at Macy’s, with the Rookery omitted on Sundays.

“Grant was terrific! Very knowledgeable and personable! Saw things we would never have found on our own.”

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Chicago's Chinatown Food and Walking Tour - Yummy Yummy Noodles brings regional comfort food
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Chicago’s Chinatown Food and Walking Tour

6.Chicago’s Chinatown Food and Walking Tour

★★★★★★★★★★5.0 · 600 reviews · 3 hours (approx.) · from $79

Spend three hours tasting five generous Chinese food specialties with an English-speaking guide in Chicago’s Chinatown. You’ll visit Phoenix Restaurant, Yummy Yummy Noodles, Xi’an Cuisine, Lao Sze Chuan, and Chiu Quon Bakery, while seeing Chinatown Square, Pui Tak Center, the Gateway, and Nine Dragon Wall.

“Lillian, our guide was very knowledgable and made the tour fun. The food was plentiful and delicious. Would recommend this tour.”

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Chicago: Secret Interiors Architecture Walking Tour - Starting beneath the Clinton Street sign at Union Station
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Chicago: Secret Interiors Architecture Walking Tour

7.Secret Interiors Architecture Walking Tour

★★★★★★★★★★4.9 · 498 reviews · 2 hours · from $35

Walk from Union Station through Chicago’s Loop with guides such as Grant, Talia, Annie, and Angel. See the Rookery, Field, Marquette, Palmer House, Cultural Center, and Marshall Field buildings, while learning how architects solved lighting and structural problems.

“Our tour guide - Grant was super awesome. He let us know so much history of the city and its intricate architecture all along the downtown area.a”

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Chicago Gangster and Food Walking Tour - Harry Caray’s tunnel and the gangster setting
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Chicago Gangster and Food Walking Tour

8.Chicago Gangster and Food Walking Tour

★★★★★★★★★★5.0 · 471 reviews · from $79

Walk from River North to the Gold Coast while tasting Chicago prime-cut steak, deep-dish pizza, and a classic hot dog. Hear stories at Harry Caray’s tunnel, see Tommy Gun marks at Holy Name Cathedral, and learn from guides such as Avery, Taka, Ty, or Baylor.

“Loved learning the history of the Irish North and Italian South gangs and the clever ways they stuck it to each other. Pizza was phenomenal, and Harry Carrys basement was so interesting with the tunnels!”

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Chicago Mobs and Haunts Walking Tour - The Exchequer and Capone’s old Chicago
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Chicago Mobs and Haunts Walking Tour

9.Chicago Mobs and Haunts Walking Tour

★★★★★★★★★★4.5 · 383 reviews · 1 hour 30 minutes to 2 hours (approx.) · from $34

Walk from the Congress Plaza Hotel to North Michigan Avenue with guides such as Lark, Alyssa, Bryson, or Mitchell. Expect mob lore, ghost stories, Chicago history, and outdoor stops, not private building access. The roughly two-mile route takes 90 minutes to two hours.

“It was a great tour full of history and crazy stories about notorious mobsters of Chicago. Lark did a wonderful job!”

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Chicago Walking Tour: Historic Treasures of Chicago - Palmer House: the indoor highlight
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Chicago Walking Tour: Historic Treasures of Chicago

10.Chicago Walking Tour: Historic Treasures of Chicago

★★★★★★★★★★5.0 · 362 reviews · from $35

Walk from the Chicago Architecture Center to the Chicago Cultural Center with a certified guide such as Bob, Jim, John, or Maureen. See the Wrigley Building, Palmer House, Carbide and Carbon Building, and Reliance Building, with time for striking interiors and Chicago stories.

“This tour was very informative and very interesting. Bob P. did a great job is our tour leader. I would definitely recommend the tour.”

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Chicago: Underground Pedway & Downtown Secrets Walking Tour - Meeting at 120 North LaSalle Street
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Chicago: Underground Pedway & Downtown Secrets Walking Tour

11.Underground Pedway & Downtown Secrets Walking Tour

★★★★★★★★★★4.7 · 268 reviews · 2 hours · from $35

You’ll spend two hours with an English-speaking guide such as Heath, Kaylee, Adam, or Colleen, learning to navigate Chicago’s Pedway. Expect about 1.5 miles of walking, staircases, stained glass, underground pools, public art, and a striking interior near Millennium Park.

“The tour was Wonderful, learning about the Pedway: what it was, how it started and how to get around. Learning more history of this great City of Chicago is always a highlight, there was many pieces of information and history, we had not heard before or quite in the same way as was presented on this tour. The tour guide was very knowledgeable as well as had a binder of information, pictures of what he was discussing and vintage pictures of Chicago; which were very interesting. Thoroughly enjoyed learning about Pedway, its pathways, origins and Downtown secrets, and loved learning alternate ways to traverse this great City of Chicago.”

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Haunted Chicago Booze and Boos Ghost Walking Tour - Starting at Glascott’s Saloon and its Prohibition past
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Haunted Chicago Booze and Boos Ghost Walking Tour

12.Haunted Chicago Booze and Boos Ghost Walking Tour

★★★★★★★★★★5.0 · 266 reviews · 2 hours 30 minutes (approx.) · from $35

Walk Chicago’s Lincoln Park with a costumed Nightly Spirits guide such as Katie, Lara, or Mallory. Hear tales of John Dillinger, haunted bars, Oz Park, and old speakeasies while stopping for drinks at three pubs. Drinks cost extra, and the 21-and-over tour has a maximum of 12 people.

“Seemed unorganized and the guide didn’t seem excited to tour. We left early because it seemed just like a bar-hop and not an informative walking tour. We wanted fun, engaging, and lively and both the guide and the other guests looked and seemed bored. We left early so we could bar-hop on our own.”

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Chicago: Gangsters and Food Tasting Walking Tour - First taste: Chicago pizza in two very different styles
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Chicago: Gangsters and Food Tasting Walking Tour

13.Gangsters and Food Tasting Walking Tour

★★★★★★★★★★4.6 · 228 reviews · 2 hours · from $81

Walk about one mile through Chicago’s River North with an English-speaking guide such as Alan, Baylor, Talia, or Sarah. Stop for deep dish and tavern-style pizza, steak, and a Chicago hot dog, then visit old gangster sites, including a Prohibition-era tunnel linked to Capone.

“It’s hard to say, but Allen had information we were not aware of. His subject matter was phenomenal. His personality was so personable I felt I knew him. The food was wonderful. Tip for future goers. Don’t eat before the tour.”

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Chicago: Treasures of the Golden Age Walking Tour - Beginning inside the Chicago Architecture Center
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Chicago: Treasures of the Golden Age Walking Tour

14.Treasures of the Golden Age Walking Tour

★★★★★★★★★★4.8 · 206 reviews · 2 hours

Walk through Chicago’s Loop with a Chicago Architecture Center certified guide, visiting the Cultural Center, Macy’s on State, Palmer House, and other Golden Age landmarks. Expect strong architecture stories, some interior access, and plenty of pavement. English tour, rain or shine.

“The buildings we saw and what we learned about them. The docent was engaging and knowledgeable.”

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Chicago Walking Tour: A Walk Through Time - Starting at the Chicago Architecture Center
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Chicago Walking Tour: A Walk Through Time

15.Chicago Walking Tour: A Walk Through Time

★★★★★★★★★★5.0 · 181 reviews · from $35

Walk through Chicago’s architectural story in chronological order with a certified Chicago Architecture Center guide. In 90 minutes, you’ll see cast iron, Art Deco, postmodern design, Aqua Tower, and Lakeshore East, then return to the Center’s galleries.

“We were visiting for two days from London- excellent knowledgeable walking guide. Loved all the quirky facts about various iconic buildings. Added bonus to be able to view the foyer of the Automobile association building.”

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New in Chicago Walking Tours

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★ 5.0Chicago Architecture Walking Tour: Incredible Art Deco InteriorsFrom $3585 reviews
★ 4.6The Ultimate Foodie Walking Tour with Tasty StopsFrom $7592 reviews
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