Top 10 Walking Tours in Chicago

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 crime tales and ghost stories tied to the Palmer House, Riverwalk, Chicago Theatre, and Congress Plaza Hotel. Guides such as Taka, Sophia, Tanner, and Avery are known for clear storytelling. A minibus option is also available.

“The guide had a loud voice so everyone could hear and she spoke fast and clear. The tour was interesting, so happy I booked it”

Check availability →Read our full review

2.Chicago Favorites Ultimate Food and Walking Tour

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

Walk about 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, then use the included two-hour bike or kayak rental within three days.

“This tour was great! We got to try all the most famous Chicago foods while learning all about the city. Jessika was an excellent guide. She told captivating stories and kept us entertained throughout! We had a great time!”

Check availability →Read our full review

3.Gangsters and Ghosts Guided Walking Tour

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

Walk 1.5 miles through Chicago’s South Loop with an English-speaking historian guide. Hear Al Capone stories, ghost tales, and local lore while visiting the Riverwalk, Death Alley, Palmer House, the Chicago Theatre, and Congress Hotel. Guides such as Max, Baylor, Tanner, and Chris are known for lively storytelling.

“Excellent - really fun and informative and just the right pace. Absolutely excellent - highly recommend our guide Tanner.”

Check availability →Read our full review

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

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

Spend 4.5 hours with a local guide such as Dave, Rich, or Dash, walking 3 to 4 miles through Chicago’s Loop and River North. You’ll see the Chicago Theatre, Pedway, Riverwalk, Wrigley Building, Tribune Tower, and Millennium Park while sampling deep-dish pizza, Italian beef, a Chicago hot dog, and more.

“Great city tour! Chicago Dave was awesome and full Of information, it was fun and easy! Would highly recommend. Learned a lot about Chicago!”

Check availability →Read our full review

5.Chicago’s Secret Interiors Architectural Walking Tour

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

Walk Chicago’s Loop with guides such as Ethan, Grant, Ty, and Matthew, visiting grand lobbies, mosaics, domes, and historic halls. This roughly two-hour tour links Union Station, the Rookery, Palmer House, and Marshall Field, with the Rookery omitted on Sundays.

“I’ve done several Chicago tours and this one is up there with the architecture boat tour as the best ones. Shout out to Matt, our tour guide - he was very informative.”

Check availability →Read our full review

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 guide such as Greg, Joe, Lillian, York, or Mickey. Taste dim sum, hand-pulled noodles, Xi’an flatbread, Sichuan chicken, and a Portuguese egg tart while visiting Chinatown Square, Pui Tak Center, the Gateway, and Nine Dragon Wall.

“This was a wonderful cultural experience with interesting experiences and restaurants we would’ve never found on our own. Our guide was knowledgeable and enjoyed learning the history about Chicago’s Chinatown. The walking was easy and enjoyed honestly every food stop. To learn about Chicago”

Check availability →Read our full review

7.Secret Interiors Architecture Walking Tour

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

Meet your English-speaking guide, including Grant, Talia, Annie, Angel, or Matthew, inside Union Station. Walk through Chicago’s Loop to see remarkable interiors at the Rookery, Marquette Building, Palmer House, Cultural Center, and more. Expect about 90% outdoors, with plenty of history, design details, and photo stops.

“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.”

Check availability →Read our full review

8.Chicago Gangster and Food Walking Tour

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

Spend about two hours walking from River North to the Gold Coast, stopping for steak at Harry Caray’s, deep-dish pizza in a former gangster’s mansion, and a classic Chicago dog. Guides such as Taka, Avery, Ty, and Baylor lead groups of up to 15.

“Taka is a great story teller! We throughly enjoyed our time exploring the city with a fun gangster twist and food. Loved the Chicago Hot Dog the best!”

Check availability →Read our full review

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 the River near Michigan Avenue with guides such as Lark, Alyssa, Bryson, and Mitchell. Expect mob tales, ghost stories, Chicago history, outdoor stops, city noise, and roughly two miles of walking. The tour lasts about 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!”

Check availability →Read our full review

10.Chicago Walking Tour: Historic Treasures of Chicago

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

Walk from the Chicago Architecture Center through the Loop with a certified docent, seeing the Wrigley Building, Palmer House, Carbide and Carbon Building, Reliance Building, and Chicago Cultural Center. Small groups, striking interiors, and guides such as Jim, John, Bob, and Maureen make this a strong introduction to Chicago architecture.

“Rainy day so my son and I debated going. Glad we participated as the docent Beth was excellent. Knowledgeable, interesting and responsive to our questions. Fascinating blend of design and Chicago history.”

Check availability →Read our full review