10 Walking Tours in Chicago, Ranked by What You Get

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 stories, ghost accounts, and tales of Al Capone. Stops include Millennium Park, the Palmer House, the Riverwalk, the Chicago Theatre, and the Congress Plaza Hotel. Guides such as Taka, Sophia, Tanner, and Avery are known for clear delivery and strong storytelling.

“Taka, with her passionate love of history, gave us a fascinating introduction to the history of Chicago. She switched easily from Al Capone and gang warfare of the prohibition era and then told of tragic loss life on the SS Eastland. So many great stories, we loved it!”

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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 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. The $84.99 tour also includes a two-hour bike or kayak rental, with seasonal limits.

“The food walking tour was awesome! Our tour guide, Gabe, was fantastic! He was very informative and a great person to show us around a small part of the city. I wasn't sure if this tour would include enough food, but I was so wrong! At the end of the tour, my wife and I were both stuffed! The food at all of our stops was really good. Nothing that blows your mind away, but all really tasty and fresh! Lots of walking, lots of food and lots of great facts/stories about Chicago.”

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3.Gangsters and Ghosts Guided Walking Tour

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

Follow a historian guide through Chicago’s South Loop, once a Prohibition-era vice district. Hear stories about Al Capone, secret tunnels, and reported hauntings at Death Alley, the Palmer House, Chicago Theatre, and Congress Hotel. The 1.5-mile route includes a 20-minute break and works best for adults, older children, and true-crime fans.

“Tanner was really nice Guide. It was a good interesting tour, with much of deap facts.”

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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 Chicago with a local guide such as Dave, Rich, Dash, or John. See the Chicago Theatre, Pedway, Riverwalk, Wrigley Building, Tribune Tower, Millennium Park, and the Bean while sampling popcorn, deep-dish pizza, a Chicago hot dog, Italian beef, and more. Expect 3 to 4 miles of walking and a full meal’s worth of food.

“It was a good way to get a feel for Chicago. I thought I had tried deep dish pizza in California, but it turns out a Chicago deep dish pizza was a true, brand new culinary experience. And I was glad I got to ride the "elevated".”

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5.Chicago’s Secret Interiors Architectural Walking Tour

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

Walk from Chicago Union Station through the Loop with a guide such as Ethan, Grant, Ty, or Matthew, entering grand buildings most people pass without noticing. See the Rookery, Marquette Building, Palmer House, Macy’s Tiffany dome, and more. The route is about two hours, costs $35, and includes a maximum of 15 people.

“Ethan was hands down the most enthusiastic and informed tour guide I’ve had the pleasure of adventuring with. I’ve done many guided tours but his passion, energy, and knowledge were truly unparalleled. Cannot recommend the tour highly enough, and Ethan even more so.”

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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 Joe, Greg, Lillian, York, or Mickey. You’ll taste dim sum, hand-pulled noodles, Xi’an cumin lamb, Sichuan chicken, and a Portuguese egg tart, while visiting Chinatown Square, Pui Tak Center, the Gateway, and Nine Dragon Wall. Expect a hearty meal, easy walking, and a group of up to 15.

“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

Meet your English-speaking guide in Union Station’s Great Hall for a two-hour walk through Chicago’s Loop. Visit landmark interiors at the Rookery, Field Building, Marquette Building, Palmer House, Chicago Cultural Center, and Marshall Field and Company Building. Guides such as Grant, Talia, Annie, and Angel bring the buildings’ design and stories to life.

“We visited places on this tour that we would never have known about or seen on our own. Talia did a wonderful job and was very knowledgeable.”

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8.Chicago Gangster and Food Walking Tour

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

Walk from the Chicago River toward River North and Gold Coast with a guide such as Taka, Avery, Baylor, or Ty. You’ll hear Prohibition-era stories, see a gangster-era tunnel and Tommy Gun bullet holes, and taste steak, deep dish pizza, and a Chicago hot dog. The two-hour tour costs $79 and holds no more than 15 people.

“My husband booked a last minute tour and our guide Avery was great! He was so knowledgeable about the history of Chicago and we learned so much. It was so nice meeting new people and exploring a little! I highly reccomend this tour. The food we sampled was also excellent!”

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9.Chicago Mobs and Haunts Walking Tour

★★★★★★★★★★4.5 · 383 reviews · 1 hour 30 minutes to 2 hours (approx.) · from $34Best value

Walk from Congress Plaza through the Loop to North Michigan Avenue, hearing stories tied to Al Capone, haunted hotels, crime, theater tragedies, and Chicago lore. Guides such as Lark, Alyssa, Mitchell, and Bryson bring the route to life. Expect about two miles of outdoor walking, city noise, and no indoor building visits.

“The tour guide was excellent. We really appreciated that he spoke up since it was a big group. I would give 5 stars for him. One hour of the tour was around the subway tracks and he had to keep stopping for them to pass. This made the tour awful. It would of been a nice tour if it wasn't for that. I think the tour guides name was Mitchell.”

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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 guide. You’ll see the Wrigley Building, Palmer House lobby, Carbide and Carbon Building, Reliance Building, and Chicago Cultural Center. Guides such as Bob, John, Jim, and Maureen have led especially lively outings, with time for questions and architectural detail.

“Our guide, Jim, was amazing! He was very knowledgeable and thorough. I enjoyed learning about the history Chicago and would recommend this tour to anyone visiting Chicago, or locals who want to learn more about their city!”

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