Chicago · CHICAGO WALKING TOURS

The 15 Best Chicago Walking Tours

32 tours  ·  from $8

Flat, gridded and eight blocks to the mile, the Loop is made for this. The 15 below cover the bridges, the lobbies, the gangster corners and Chinatown, priced by length with a note on which ones run in winter.

Chicago: Gangsters and Ghosts Walking Tour - Starting with gangsters, tunnels, and Prohibition
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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 such as Taka, Sophia, Tanner, or Avery. Hear true crime tales, ghost stories, and Al Capone lore while visiting the Palmer House, Riverwalk, Chicago Theatre, and Congress Plaza Hotel. A minibus upgrade is also available.

“Tour guide (Sophia) was fantastic. Not only did she have great stories to share, she shared them in a theatrical way that made them more interesting and entertaining! I was with my 18 year old son and we both enjoyed it equally!”

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Chicago Favorites Ultimate Food and Walking Tour - The Chicago hot dog and the no-ketchup rule
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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 1.5 miles through Chicago’s Loop with an English-speaking guide such as Gabe, Fran, Jessika, or Kevin. Taste deep-dish pizza, a Chicago hot dog, Italian beef, Garrett popcorn, and a brownie or gelato. Your ticket also includes a two-hour bike or kayak rental, with seasonal limits.

“A great opportunity to taste local cusine which was all fantastic, also there was opportunity to buy drinks in the venues but water was also provided. Jessika's knowledge of the city was great and the opportunity to see the city sights during the tour as we walked was great, we all had a great evening😃👍”

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Chicago: Gangsters and Ghosts Guided Walking Tour - Chicago Riverwalk: crime beside the water
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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

Spend two hours with an English-speaking historian guide such as Max, Baylor, Tanner, or Sophia, tracing Chicago’s gangster past and ghostly legends. Walk about 1.5 miles through the South Loop, visit Palmer House and Congress Hotel, and pause at a former gangster hangout.

“Great! Even in cold winter the walk was very enjoyable. Our guide Max was also very attentive and cheerful; We will ask for her again in our next visit soon. Hopefully not so cold!”

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Chicago in a Day: Food, History & Architecture Walking Tour - Finding the Chicago Pedway below street level
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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

Spend about 4.5 hours walking from the Chicago Theatre through the Pedway, Riverwalk, Magnificent Mile, and Millennium Park. Guides such as Dave, Dash, Rich, and John mix Chicago history with deep-dish pizza, popcorn, hot dog, and Italian beef tastings. Expect 3 to 4 miles on foot and a full meal’s worth of food.

“Dave was very knowledgeable & friendly. Freezing outside but still was able to provide a great experience both inside & outside! I would do this tour again.”

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Chicago's Secret Interiors Architectural Walking Tour - Starting at Union Station and entering the Loop
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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 to the Marshall Field Building, visiting grand lobbies, mosaics, domes, and historic hotels. Guides such as Ethan, Grant, Ty, Matthew, and Avery bring the city’s architecture and Gilded Age stories to life. Plan for about two hours on foot.

“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 - Yummy Yummy Noodles Brings Hand-Pulled 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

Meet an English-speaking guide such as Joe, Greg, Lillian, York, or Mickey for a three-hour Chinatown food walk. Expect five substantial tastings, from dim sum and hand-pulled noodles to cumin lamb flatbread and egg tarts, plus stops at Chinatown Square, Pui Tak Center, the Gateway, and Nine Dragon Wall.

“Great tour with plenty of stops and Chinatown history throughout. I was stuffed by the end! Great pace as well.”

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Chicago: Secret Interiors Architecture Walking Tour - Meeting Grant, Talia, Annie, Angel, and the other guides
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Chicago: Secret Interiors Architecture Walking Tour

7.Secret Interiors Architecture Walking Tour

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

Meet your guide inside Union Station and walk through Chicago’s Loop to see the Rookery, Field Building, Marquette Building, Palmer House, Cultural Center, and Marshall Field building. Guides such as Grant, Talia, Annie, and Angel explain the art, engineering, and stories behind these remarkable interiors.

“It was a very informative tour with beautiful buildings and a funny, knowledgeable guide.”

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Chicago Gangster and Food Walking Tour - Deep-dish pizza inside a former mansion
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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 with a guide such as Taka, Avery, Baylor, or Ty. See a gangster-era tunnel, bullet holes at Holy Name Cathedral, and taste steak, deep dish pizza, and a Chicago hot dog. Groups are capped at 15.

“Had a great tour with Baylor. We were the only ones on this tour so had all of her knowledge directed at us only. Interesting tour and Baylor was very chatty and friendly!”

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Chicago Mobs and Haunts Walking Tour - Starting at the Congress Plaza Hotel
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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

Walk from the Congress Plaza Hotel to North Michigan Avenue, hearing stories of Al Capone, haunted hotels, the Chicago Loop, and the Alley of Death. Guides such as Lark, Bryson, Alyssa, and Mitchell bring the past to life, but expect outdoor storytelling rather than indoor visits.

“It’s great walk about. Gives you a really good plan for dinner after. I have lived in Chicago for 3 years, had some friends in Ave they loved it. Lark was a badass. Really knew his stuff. Way to talk to and actually interested in it. Easy to talk to. 10/10.”

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Chicago Walking Tour: Historic Treasures of Chicago - Starting at the Chicago Architecture Center
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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 through the Loop and along Michigan Avenue with guides such as Bob, Jim, John, or Maureen. See the Wrigley Building, Palmer House, Reliance Building, Carbide and Carbon Building, and Chicago Cultural Center in two focused hours.

“Maureen, our tour guide, was knowledgeable, friendly, invited questions, and gave backstories for the various building, enhancing our insight as to life in Chicago!!”

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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

Follow an English-speaking guide such as Heath, Kaylee, Adam, or Colleen through Chicago’s confusing Pedway system. Walk about 1.5 miles, climb several staircases, find stained glass, public art, unusual interiors, and finish near Millennium Park.

“A wonderful overview of the city. Very knowledgable guide”

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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

Join a costumed Nightly Spirits guide for a 2.5-hour walk through Lincoln Park, stopping at three historic bars and spooky landmarks. Hear stories tied to Prohibition, John Dillinger, Chicago’s Fire Department, and local ghosts. Drinks are extra, and the tour is limited to 12 people.

“Chicago has a lot of very cool ghost experiences as well some great venues to hear about them. Our guide - Katie was awesome. She made it very personalized.”

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Chicago: Gangsters and Food Tasting Walking Tour - Meeting at Hoyt’s beside the Chicago River
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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 Peyton. Taste steak, deep dish and tavern-style pizza, and a Chicago hot dog while visiting gangster sites, a former brothel, a cathedral, and an old Capone-era tunnel.

“We had a great time on this tour and the food was so good! Our tour guide, Talia was extraordinary and very knowledgeable about mob history! Definitely worth going!!”

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Chicago: Treasures of the Golden Age Walking Tour - Starting at 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 and uncover the stories behind Beaux-Arts, neo-Gothic, and neo-Georgian landmarks. You’ll see the Chicago Cultural Center, Macy’s on State, Palmer House, and more during this two-hour English tour.

“Tim is a great tour guide, and when combined with interesting things to see makes it an excellent tour!”

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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 history in chronological order with a professional Chicago Architecture Center guide. In 90 minutes, you’ll see cast iron, Art Deco, Post-Modern design, Aqua Tower, and Lakeshore East, then finish with access to the center’s galleries.

“Very knowledgeable guide. Super personable and answered all questions the group had. Did not feel rushed nor did it feel too long and dragged on”

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New in Chicago Walking Tours

★ 4.0Chicago Riverwalk Self-Guided Walking TourFrom $146 reviews
★ 4.5Chicago’s Gold Coast Hidden History: A Self-Guided Audio WalkFrom $77 reviews
★ 4.5Downtown Chicago TV and Movie Sites Guided Walking TourFrom $4423 reviews
★ 5.0Downtown Loop & Millennium Park 2 Hour Walking TourFrom $495 reviews
★ 5.0Chicago Walking Tour: The Magnificent MileFrom $3534 reviews
★ 5.0Oktoberfest Walking Brewery Tour in Malt RowFrom $3928 reviews
★ 4.5Chicago Millennium Park Self-Guided Walking TourFrom $145 reviews
★ 4.7Must See Chicago 90 minute Walking Tour73 reviews
★ 4.5River North Food Walking TourFrom $8988 reviews
★ 5.0Chicago Walking Tour: Must-See ChicagoFrom $3591 reviews
★ 5.0Chicago Architecture Walking Tour: Incredible Art Deco InteriorsFrom $3585 reviews

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