On Foot · CHICAGO WALKING TOURS

Walking Tours in Chicago: Our 4 Favourites

4 tours  ·  from $36 a head

Every trip has one free morning too few. These 4 walking tours in Chicago earn the slot, priced and timed so you can decide in minutes and get back to packing.

Chicago: Gangsters and Ghosts Walking Tour - The Loop and Chicago’s Prohibition past
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Chicago: Gangsters and Ghosts Walking Tour

1.Gangsters and Ghosts Walking Tour

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

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

“Taka was so incredibly knowledgeable. She taught me so many things about Chicago. I had no idea and I’ve been living in Chicago. Almost my whole life. The way that she tells a story was so intriguing and engaging. She really made everyone in our group feel included Read more”

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Chicago Favorites Ultimate Food and Walking Tour - The Chicago hot dog lesson
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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 deep dish, hot dogs, Italian beef, brownies and popcorn while exploring Chicago landmarks on a relaxed 3-hour walking tour.

“Fun, funny, and informative guide (Gabe)!! Learned a lot about the food, history, and architecture of Chicago! Nice variety of delicious food!”

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Chicago: Gangsters and Ghosts Guided Walking Tour - Meeting outside Hoyt’s Tavern
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Chicago: Gangsters and Ghosts Guided Walking Tour

Chicago Loop District Food Tour with Deep Dish & Beef Sandwich - LaSalle Street and the Financial District
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Chicago Loop District Food Tour with Deep Dish & Beef Sandwich

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

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

Taste Chicago classics, from deep dish to Italian beef, while exploring Loop architecture on a three-hour small-group walking tour.

“Our guide Danny was excellent. He had so much information to share with the group about Chicago in general, several famous buildings, the restaurants we visited and the food we ate. At the beginning, he had all of our names memorized and kept good track of us throughout the tour. The food was a great representation of famous Chicago treats and I learned so much from him.”

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