The 15 Best Walking Tours in Chicago

Chicago: Gangsters and Ghosts Walking Tour - Millennium Park and the Bean with a new set of stories

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

Explore Chicago’s Loop through true gangster tales, Al Capone sites, haunted hotels, and ghost stories on a lively two-hour walking tour.

“It was a very cold, windy Chicago night but the tour guide braved it out so we did too--and so glad we did! It was interesting listening to all of the stories about Chicago while wallking around the streets at night. We really enjoyed the tour but will never swim in the water in and around Chicago! Lol”

Check availability →Read our full review

Food, Food & Drink, Tour Reviews, Tours, Walking Tours

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

Taste Chicago classics, see Loop landmarks, and learn local stories on a three-hour food walk with a free bike or kayak rental.

“This is tough! Our tour guide Fran was absolutely amazing and had great energy, but I’m not sure I would recommend this food tour. My family and I did the Architecture Boat Tour the day before and this shared the same concept- they both had the same exact information, so that became very repetitive. The food itself was also OK. Nothing amazing or worth wild so we were all a bit disappointed because a lot of the reviews said, it’s the best!”

Check availability →Read our full review

Chicago Gangster & Prohibition Tours, Chicago Ghost Tours, Guided, Tour Reviews, Tours, Walking Tours

Chicago: Gangsters and Ghosts Guided Walking Tour

3.Gangsters and Ghosts Guided Walking Tour

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

Explore Chicago’s gangster past and ghost lore on a historian-led South Loop walk through Death Alley, the Riverwalk, and haunted hotels.

“Sophia was very informative and very friendly! Was a last minute book and we enjoyed it, especially the Palmer brownie!”

Check availability →Read our full review

Chicago Architecture Tours, Food, Food & Drink, Historical Tours, Tour Reviews, Tours, Walking Tours

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

Taste deep-dish pizza, hot dogs, Italian beef, and Chicago architecture on a small-group walking tour of the Loop and River North.

“David was an awesome guide of the city. Chicago is an amazing town and we learned so much. The food and architecture is top-notch. We had a great time and our group was fun!”

Check availability →Read our full review

Chicago Architecture Tours, Tour Reviews, Tours, Walking Tours

Chicago’s Secret Interiors Architectural Walking Tour

5.Chicago’s Secret Interiors Architectural Walking Tour

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

Explore Chicago’s secret interiors, grand lobbies, mosaics, domes, and Gilded Age stories on a two-hour Loop walking tour.

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

Check availability →Read our full review

Chicago Neighborhood Tours, Food, Food & Drink, Tour Reviews, Tours, Walking Tours

Chicago’s Chinatown Food and Walking Tour

6.Chicago’s Chinatown Food and Walking Tour

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

Taste dumplings, noodles, Sichuan chicken, Xi’an flatbread, and egg tarts while exploring Chicago Chinatown with a local guide.

“This is a great tour of ChinaTown in Chicago. The food was delicious and we were stuffed! The tour guide Greg, was excellent. Plenty of breaks during the tour. Highly recommend this tour!!!!”

Check availability →Read our full review

Chicago Architecture Tours, Tour Reviews, Tours, Walking Tours

Chicago: Secret Interiors Architecture Walking Tour

7.Secret Interiors Architecture Walking Tour

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

Explore Chicago’s secret interiors, grand Loop buildings, mosaics, domes, and architectural stories on a practical two-hour walking tour.

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

Check availability →Read our full review

Chicago Gangster & Prohibition Tours, Food, Food & Drink, Tour Reviews, Tours, Walking Tours

Chicago Gangster and Food Walking Tour

8.Chicago Gangster and Food Walking Tour

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

Taste steak, deep dish, and a Chicago Dawg while exploring River North gangsters, secret tunnels, Gold Coast streets, and church bullet holes.

“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!”

Check availability →Read our full review

Tour Reviews, Tours, Walking Tours

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

Review of Chicago Mobs and Haunts Walking Tour, with mob tales, ghost stories, city landmarks, guide tips, price, route, and practical advice.

“If in winter months dress warm! You will learn of Chicago history from a talented story teller. Our tour guide, Mitchell, was very accommodating.”

Check availability →Read our full review

Historical Tours, Tour Reviews, Tours, Walking Tours

Chicago Walking Tour: Historic Treasures of Chicago

10.Chicago Walking Tour: Historic Treasures of Chicago

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

Explore Chicago’s landmark buildings on a two-hour small-group walk with expert guides, grand interiors, and Chicago Architecture Center admission.

“All tours were great--Dash, Grant and the 3rd tour I took. The Architectural River tour w/ Wade was fantastic”

Check availability →Read our full review

Tour Reviews, Tours, Walking Tours

Chicago: Underground Pedway & Downtown Secrets Walking Tour

11.Underground Pedway & Downtown Secrets Walking Tour

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

Explore Chicago’s Pedway, stained-glass halls, underground pools, public art, and downtown secrets on a two-hour guided walk.

“Navigating through the Pedway isn’t as straightforward as it seems. Genuinely appreciate the insight the guide given us on this underrated utility as well as niche knowledge of the city’s history.”

Check availability →Read our full review

Chicago Ghost Tours, Tour Reviews, Tours, Walking Tours

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

Explore Chicago’s haunted Lincoln Park bars, hear ghost stories from costumed guides, and enjoy a 2.5-hour walking tour with drinks sold separately.

“Laura was great - loved the history and ghost stories! At 2.5 hours the walking and bar visits were easy to navigate. My only recommendation would be to ask the bars to give our group special access to order our drinks.”

Check availability →Read our full review

Chicago Gangster & Prohibition Tours, Food, Food & Drink, Tour Reviews, Tours, Walking Tours

Chicago: Gangsters and Food Tasting Walking Tour

13.Gangsters and Food Tasting Walking Tour

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

Taste Chicago pizza, steak, and a hot dog while exploring Capone-era hideouts, mob landmarks, and River North with a local guide.

“Baylor was very knowledgeable and easy to spend time with during the tour. We enjoyed her company! The food was fantastic and everything was very organized. Highly recommend!”

Check availability →Read our full review

Tour Reviews, Tours, Walking Tours

Chicago: Treasures of the Golden Age Walking Tour

14.Treasures of the Golden Age Walking Tour

★★★★★★★★★★4.8 · 206 reviews · 2 hours

Explore Chicago’s Golden Age architecture on a two-hour CAC walking tour featuring Tiffany glass, grand interiors, and expert local guides.

“The tour was wonderful! The docent was well informed and a wealth of information about the city. He pointed out many areas and buildings of interest along our tour and the history behind it. We enjoyed it very much and would highly recommend it.”

Check availability →Read our full review

Tour Reviews, Tours, Walking Tours

Chicago Walking Tour: A Walk Through Time

15.Chicago Walking Tour: A Walk Through Time

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

Trace Chicago architecture from cast iron to postmodern icons on a 90-minute guided walk with Chicago Architecture Center access.

“Perfect tour. Well thought out. Loved the history woven in. So interesting that I took notes! And our docent was so approachable and entertained numerous questions from numerous attendees.”

Check availability →Read our full review