Where to Walk: the 13 Best Chicago Walking Tours

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, Avery, or Willis. Hear true Prohibition-era crime stories, visit haunted landmarks including the Palmer House and Congress Hotel, and stop at Millennium Park, the Riverwalk, and the Chicago Theatre. A minibus option is also available.

“Willis was a great story teller! Easy to find, the only wish is that we were able to stop in more places. Most of the tour is just walking outside not in actual buildings.”

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2.Chicago Favorites Ultimate Food and Walking Tour

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

Eat your way through Chicago’s Loop with an English-speaking guide such as Gabe, Fran, Jessika, or Kevin. In about three hours, you’ll sample deep-dish pizza, a Chicago hot dog, Italian beef, Garrett popcorn, and a brownie or gelato while seeing Millennium Park, the Chicago River, and famous architecture. A two-hour bike or kayak rental is included for a later date.

“The food was great! We had pizza, hotdogs, Italian beef, popcorn and brownies. The tour guide Kevin was so nice and informative!”

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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 history at Death Alley, the Riverwalk, Palmer House, Chicago Theatre, and Congress Hotel. Guides such as Max, Baylor, Tanner, and Sophia are known for lively storytelling. A 20-minute break is included.

“Our guide Chris was very clear & easy to understand. Excellent as my husband has a hearing issue, and had no problem hearing & communicating with him. He was informative & entertaining.”

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4.Chicago Loop District Food Tour with Deep Dish & Beef Sandwich

★★★★★★★★★★5.0 · 870 reviews · 3 hours (approx.) · from $84

Spend about three hours eating Chicago’s essential foods and exploring the Loop on foot. You’ll try sausage deep dish, Italian beef, a Chicago hot dog, popcorn, brownie, and a secret dish while seeing Willis Tower, the Rookery, Federal Plaza, and Millennium Park. Guides such as Danny, Eliot, Lance, Mike, and Sue are known for adding lively city stories.

“Michael was our tour guide and he was excellent. He even helped us find parking on the street .The tour starts with a short visit inside the library which was the meeting spot. He had lots of stories to tell, and he was very entertaining. He was also very knowledgeable about Chicago. I expected sample servings of all the food, but we actually had an entire slice of pizza, a half of a beef sandwich, an entire hotdog, an entire churro, an entire brownie, and a small sample bag of popcorn. The tour took exactly 3 hours as advertised. I recommend this tour and hopefully you have Michael as your…”

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5.Secret Interiors Architecture Walking Tour

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

Meet your English-speaking guide, such as Grant, Talia, Annie, Angel, or Matthew, inside Union Station’s Great Hall. Walk through the Loop to see the Rookery, Field Building, Marquette Building, Palmer House, Chicago Cultural Center, and Marshall Field and Company Building, with stories about design, engineering, and Chicago’s famous past.

“The tour was great! Grant was a great guide. Not too much walking but was able to see a lot. Lived here my whole life and hadn’t been in most of the buildings.”

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6.Underground Pedway & Downtown Secrets Walking Tour

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

Join an English-speaking guide such as Heath, Kayley, Adam, or Colleen for a two-hour, 1.5-mile walk through Chicago’s confusing Pedway. You’ll use staircases, enter beautiful buildings through lesser-known passages, see stained glass and underground swimming pools, and finish near Millennium Park.

“Kaylee was a fabulous guide for this tour. She's so passionate, knowledgeable and fun! Non of us knew much about the Chicago pedway. It was fascinating!”

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7.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 local guide. You’ll taste steak, deep dish and tavern-style pizza, and a Chicago hot dog, then visit old gangster sites including an underground tunnel linked to Capone. Guides such as Alan, Baylor, Talia, and Peyton are praised for clear storytelling and friendly service.

“it was brilliant, very enjoyable. Baylor was a great guide!”

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8.Treasures of the Golden Age Walking Tour

★★★★★★★★★★4.8 · 206 reviews · 2 hours · from $35

Walk through Chicago's Loop with a Chicago Architecture Center certified guide and see grand buildings from the 1890s to 1930s. Expect the Cultural Center's Tiffany dome, Macy's on State, Palmer House, and stories about Burnham, Sullivan, Holabird, and Roche. The two-hour tour runs rain or shine and includes Chicago Architecture Center exhibit admission.

“Great tour and very informative and insightful. Your volunteers are incredible.”

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9.Prohibition Speakeasies Bus Tour or Walking Tour

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

Choose a downtown walking tour or neighborhood bus tour led by guides such as Jonathan Knotek. Visit three or four historic speakeasy venues, hear how gangsters and high society drank during Prohibition, and receive drink suggestions at each stop. Drinks and food cost extra, and all tours are for adults 21 and over.

“Amazing historical and highly entertaining tour of Chicagos dark past! Our tour guide Jonathan was absolutely spectacular and his commentary flowed effortlessly as well did the booze at each of the fine establishments we visited throughout the city. By far the best tour and guide in Chicago. We plan on taking this again and will bring family and friends anytime they visit the city.”

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

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

Walk downtown Chicago with a local guide such as Jeff, Julia, James, or Gabe while tasting deep dish, a Chicago dog, Italian beef, Garrett’s popcorn, and a brownie or seasonal dessert. The relaxed three-hour route includes major sights and a free two-hour bike or kayak rental for a separate lakefront outing.

“This tour was awesome! A must do when visiting Chicago! Our guide was James and he was the best. Very informational, knew the city and has a great personality . Highly recommend this tour and ask for James !we went a lot of other places too and learned a lot of history .”

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11.Taste of Chinatown Food and Cultural Walking Tour

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

Spend three hours walking Chicago’s Chinatown with an English-speaking local guide, tasting dim sum, noodles, dry chili chicken, cumin lamb flatbread, and an egg tart. Guides such as Jeff and York add food and neighborhood stories while you visit the Gateway Arch, Zodiac Plaza, Nine Dragon Wall, and Pui Tak Center.

“We had the best time with York, our tour guide today!! I learned so much and fell in love with Chinatown’s food and energy. Thank you so much, York for an amazing adventure.”

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12.The Ultimate Foodie Walking Tour with Tasty Stops

★★★★★★★★★★4.6 · 92 reviews · from $75

Walk about 1.5 miles through Chicago’s Loop and nearby food districts, stopping for a Chicago-style hot dog, deep-dish pizza, and Italian beef. Guides such as Dash, Rich, and Dave add architecture and local history to the food. Groups are capped at 12, with vegetarian options available.

“Learning things about the community and history of the area”

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13.Must See Chicago 90 minute Walking Tour

★★★★★★★★★★4.7 · 73 reviews · 1h 30m · from $35

Walk through the Chicago Loop, along the Chicago River, and toward Millennium Park with a Chicago Architecture Center-trained guide. You’ll see landmark buildings from Beaux Arts to Art Deco and Modernism, then visit the CAC exhibits within seven days. Guides such as Claudia, Howard, Lori, Paige, and Anna have earned especially strong praise for clear stories and personal attention.

“The tour was very nice. Paige was amazing, 10 out of 10.”

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