14 Chicago Walking Tours Worth Booking

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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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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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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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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5.Chicago’s Secret Interiors Architectural Walking Tour

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

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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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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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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8.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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9.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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10.Prohibition Speakeasies Bus Tour or Walking Tour

★★★★★★★★★★4.8 · 168 reviews · 3 - 4 hours · from $47

Choose a downtown walking tour with Jonathan Knotek or a neighborhood bus tour through four Chicago districts. You’ll visit three or four historic speakeasy sites, hear stories of gangsters and high society, and buy period-inspired drinks along the way.

“The tour was perfect. If you are in Chicago, so you have to book the prohibition tour. You will learn a lot about the prohibition and speakesias. The tour is super done and you will definitly enjoy it.”

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11.Classic Food & Walking Tour with Free Bike or Kayak

★★★★★★★★★★4.9 · 145 reviews · 3 hours · from $84

Walk downtown with a certified local guide, tasting deep dish, a Chicago dog, Italian beef, Garrett’s popcorn, and a Chicago-born dessert. Day routes visit Millennium Park and Cloud Gate. Your ticket also includes a two-hour bike or seasonal kayak rental for a second look at the lakefront.

“Jeff was amazing he made us all feel like family. He memorized all our names. My family loved his passion for Chicago”

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12.Taste of Chinatown Food and Cultural Walking Tour

★★★★★★★★★★4.9 · 97 reviews · 3 hours · from $84

Start with dim sum and tea at Phoenix Restaurant, then follow an English-speaking local guide through Chinatown for noodles, dry chili chicken, cumin lamb flatbread, and a Portuguese-style egg tart. Along the way, see the Gateway Arch, Zodiac Plaza, Nine Dragon Wall, and Pui Tak Center.

“What a delicious informative Tour. The Guide, Jeff, was brilliant, informative and had very good knowledge about the topic spiked with personal suggestions”

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13.The Ultimate Foodie Walking Tour with Tasty Stops

★★★★★★★★★★4.6 · 92 reviews · from $75

Spend two hours walking about 1.5 miles through Chicago’s Loop and nearby food districts with an English-speaking guide such as Dash, Rich, or Dave. Taste a Chicago hot dog, deep-dish pizza, Italian beef, and a local treat while learning about architecture, immigrant cooking, and the best places to eat next.

“The tour was nice. It was detailed with all the things that has taken place in the city and how it was developed. The quality for the price was on par. The tour guide did a good job with everything.”

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14.Must See Chicago 90 minute Walking Tour

★★★★★★★★★★4.7 · 73 reviews · 1h 30m

Walk from the Chicago Architecture Center through the Loop, along the Chicago River, and to Millennium Park with a CAC-trained English guide. See the Wrigley and Tribune buildings, Art Deco towers, modern skyscrapers, and The Bean, then visit the CAC exhibits within seven days.

“I had a fantastic tour with Anna. I was lucky to be the only one on the tour which was great. Anna shared a lot of interesting information and stories about Chicago’s iconic buildings. It was a very good mixture of architecture, art and history of Chicago. The time passed quickly and I could have continued the walk for much longer. I can only recommend doing this tour.”

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