Chicago · CHICAGO WALKING TOURS

The 15 Best Chicago Walking Tours

88 tours  ·  from $5 a head

The Loop is flat, dense and built to be walked. These 15 cover architecture, gangsters, ghosts and food, priced by length, with a note on the ones that keep going after dark.

Chicago: Gangsters and Ghosts Walking Tour - From Millennium Park to the Palmer House
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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, hearing stories of Al Capone, bootleggers, and reported hauntings at places such as the Palmer House and Congress Plaza Hotel. The tour lasts about two hours, with frequent stops and a refreshment and restroom break. A bus upgrade is available, with one stop at Harry Caray’s Italian Steakhouse.

“This was a very interesting and also funny tour! Our guide Tanner was amazing!!! We had a very good time”

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Chicago Favorites Ultimate Food and Walking Tour - Hot dogs, Italian beef and the art of eating neatly
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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 1.25 to 1.5 miles through downtown Chicago with a local English-speaking guide, stopping for deep-dish pizza, a Chicago hot dog, Italian beef, Garrett’s popcorn and a sweet treat. You’ll pass landmarks such as Millennium Park and the Chicago River. The tour lasts about three hours, includes food, and comes with a two-hour bike or kayak rental to use within three days before or after.

“Very fun, informative, and delicious tour of Chicago with our great guide Gabe, who was super personable and humorous. Highly recommend!”

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Chicago: Gangsters and Ghosts Guided Walking Tour - The Riverwalk and Death Alley
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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

Join an English-speaking historian guide for a 1.5-mile walk through Chicago’s South Loop, where Prohibition-era gangsters and ghost legends meet at landmarks including the Riverwalk, Palmer House and Congress Hotel. The $36 tour includes entry inside the Palmer House and Congress Hotel, plus a midway break at a former gangster hangout.

“Tanner was really nice Guide. It was a good interesting tour, with much of deap facts.”

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Chicago in a Day: Food, History & Architecture Walking Tour - Chicago River views and a stretch along the Mag Mile
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Chicago in a Day: Food, History & Architecture Walking Tour

4.Chicago in a Day: Food, History & Architecture Walking Tour

★★★★★★★★★★5.0 · 1,153 reviews · 4 hours 30 minutes (approx.) · from $100

Walk about 3 to 4 miles over roughly 4.5 hours with a local guide and no more than 11 other people. You’ll pass the Chicago Theatre, the Riverwalk, the Wrigley Building and Millennium Park, with tastings of Chicago favorites along the way. Guides have included Dave, Rich and Dash. Food is meant to add up to a meal, but the main tastings may come later in the tour.

“Informative; our guide Dave was passionate and knowledgeable. It was great to try Chicago’s iconic foods too!”

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Chicago's Secret Interiors Architectural Walking Tour - The Rookery’s light court and Wright details
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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 the Loop to the former Marshall Field building, popping into remarkable interiors such as the Rookery, Palmer House and Marquette Building. Guides including Ethan, Grant, Ty and Matthew bring Chicago’s architecture and Gilded Age stories to life. The route takes about two hours, with the Rookery omitted on Sundays.

“Ty was very accommodating, informative and entertaining. Lots of details and a sharp POV. A great value for the money”

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Chicago's Chinatown Food and Walking Tour - Xi’an flatbread and Sichuan heat
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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 about three hours walking Chicago’s Chinatown with an English-speaking local guide and a small group of up to 15. The route pairs five restaurant and bakery tastings with stops at Chinatown Square, the Pui Tak Center and the Nine Dragon Wall. Come hungry: portions can add up to a full meal.

“What a great experience! I was able to taste food from different regions on China that are produced locally in the community as well as learning a bit about local Chicago history. The wonderful weather didn’t hurt at all. Highly recommend”

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Chicago: Secret Interiors Architecture Walking Tour - Finding the Rookery’s details
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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 the Loop with an English-speaking guide, stopping at landmarks including the Rookery, Palmer House, and Chicago Cultural Center. Expect stories about design, engineering, and the people who shaped the city, plus chances to see interiors you might otherwise pass by. The Rookery is closed Sundays, when the tour visits an alternative stop.

“The tour was very beautiful, interesting, and informative. Our guide Talia was extremely knowledgeable and made the tour very enjoyable. We’ve lived in the area our whole lives and we learned way more than we thought we would have. Great tour, great guide.”

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Chicago Gangster and Food Walking Tour - Gold Coast: a classic Chicago hot dog
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Chicago Gangster and Food Walking Tour

8.Chicago Gangster and Food Walking Tour

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

Walk River North and the Gold Coast with a guide, hearing Chicago gangster stories as you sample steak, deep-dish pizza, and a Chicago hot dog. You’ll see the tunnel at Harry Caray’s and stop by Holy Name Cathedral, where bullet holes from a 1920s shooting are still visible. The tour lasts about two hours and caps groups at 15.

“Avery was awesome, he went above and beyond Great tour, wonderful tour guide We all had a great time Loved it Sue Hockman”

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Chicago Mobs and Haunts Walking Tour - The Loop puts crime and the elevated train in the frame
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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 $34Best value

Follow a local guide through central Chicago for 90 minutes to two hours, hearing mob history and ghost stories at places including the Congress Plaza Hotel, the former 226 Club, and West Couch Place. Expect an outdoor walking tour, not indoor visits. Guides such as Lark, Alyssa, Bryson, and Mitchell have led lively, story-focused outings.

“Filled with history facts about Chicago as well as mysterious lore! Great story telling and wonderful to learn some Chicago history! Lark was an awesome guide!”

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Chicago Walking Tour: Historic Treasures of Chicago - Look up at the Wrigley Building
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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 Michigan Avenue, State Street, and the Loop with a certified docent, stopping at the Wrigley Building, Palmer House, Carbide and Carbon Building, Reliance Building, and Chicago Cultural Center. The small-group tour includes Chicago Architecture Center gallery admission. Docents have included Bob, John, Jim, Maureen, and Laurel, though your guide may differ.

“Our tour guide John was extremely knowledgeable about the history and architecture of Chicago. We’re very glad we did the tour.”

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Chicago: Underground Pedway & Downtown Secrets Walking Tour - Look closely at the passages and interiors
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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

Learn to navigate Chicago’s underground Pedway on a two-hour walk of about 1.5 miles. An English-speaking guide leads you through hidden passages, stained-glass hallways, public art, and unusual building interiors, ending near Millennium Park. Guides have included Adam, Heath, Kaylee, and Colleen.

“Heith was our tour guide! He was very honest and passionate about the good, bad, and ugly about this interesting underground system. He was very knowledgeable about the buildings and history. We learnt lots and it makes you think about Chicago in a different light. Heith one day you will be the pedway-zar!”

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Haunted Chicago Booze and Boos Ghost Walking Tour - Lincoln Park’s alleys and ghost stories
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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

Spend about two and a half hours walking through Lincoln Park with a costumed local guide, hearing ghost stories and neighborhood history. Stop for drinks at Glascott’s Saloon, Lilly’s, and Hook and Ladder, and pass Oz Park, King of Cups, and the Red Lion. Guides have included Katie, Lara, Mallory, and Bobby. Drinks cost extra.

“We had so much fun on our Booze and Boos tour. Our tour guide was Katie and she was so enthusiastic and made me and my two best friends enjoy every second of the tour. She kept us engaged every step of the way and it was a great way to end our vacation.”

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Chicago: Gangsters and Food Tasting Walking Tour - The tunnel beneath Harry Caray’s
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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 a mile through River North with a local English-speaking guide, sampling Chicago steak, pizza, and a hot dog while hearing stories of Capone-era gangsters. Stops include an old tunnel in Harry Caray’s restaurant, a former gangster hideout, and sites tied to notorious Chicago history. Guides such as Alan, Talia, and Baylor have led the tour.

“Our guide Baylor was great! She was well informed and friendly. The food was great. Our favorite part was going down to see hidden tunnel in Harry Caray restaurant. Thank you”

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Chicago: Treasures of the Golden Age Walking Tour - Macy’s on State and the department-store era
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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 Chicago’s Loop with a guide trained by the Chicago Architecture Center, exploring landmark buildings from the 1890s through the 1930s. Expect Beaux Arts, neo-Georgian and neo-Gothic details, stories about the people behind them, and a chance to look inside some buildings. The route includes the Chicago Cultural Center, Macy’s on State and the Palmer House.

“Thoroughly enjoyed this walking tour & our guide. She was pleasant & very knowledgeable. This tour makes your time in this city much more memorable.”

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Chicago Walking Tour: A Walk Through Time - From cast iron to the Chicago Motor Club
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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 history in chronological order with a professional, certified guide. This 90-minute tour visits landmarks including the cast-iron-fronted building at 177 N State St, the Chicago Motor Club, Aqua Tower, NBC Tower and the Carbide and Carbon Building. Your $35 ticket also includes admission to the Chicago Architecture Center galleries.

“My husband and I had a wonderful time at this tour. Our guide was very knowledgeable and fun. I definitely recommend.”

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New in Chicago Walking Tours

★ 5.0Walking Tour: Historic Chicago Pubs in River North and the LoopFrom $659 reviews
★ 5.0The Deep Pockets Of Graceland Cemetery Walking TourFrom $459 reviews
★ 4.0Chicago Riverwalk Self-Guided Walking TourFrom $146 reviews
★ 5.0Retro River North Walking TourFrom $04 reviews
★ 4.5Private Downtown Chicago TV and Movie Sites Guided Walking TourFrom $1323 reviews
★ 5.0Walking Tour: Chicago’s Prairie Ave Dist. – Street of the EliteFrom $8020 reviews
★ 4.5Downtown Chicago TV and Movie Sites Guided Walking TourFrom $4423 reviews
★ 4.5Chicago Haunted Ghost Tour GPS Self-Guided Walking TourFrom $93 reviews
★ 5.0Chicago’s Midway, Movies, and the 1893 World’s Fair Walking TourFrom $495 reviews
★ 5.0Oktoberfest Walking Brewery Tour in Logan SquareFrom $2510 reviews
★ 5.0Chicago Seasonal Stroll Walking Tour of Holiday AttractionsFrom $445 reviews
★ 5.0Walking Tour: Pilsen Chicago – Creativity & Community7 reviews
★ 4.5Chicago History and Architecture Walking Tour with Boat CruiseFrom $10410 reviews
★ 5.0Chicago Walking Tour of Highlights with Free Bike or Kayak RentalFrom $445 reviews
★ 5.0Chicago Ghosts & Haunted History Walking TourFrom $4911 reviews

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