USA · WALKING TOURS IN CHICAGO

4 Walking Tours in Chicago to Build a Day Around

4 tours  ·  from $36 a head

Good walking tours in Chicago fill up weeks ahead and the great ones go first. Below: the 4 to book early, what each includes and how they differ.

Chicago: Gangsters and Ghosts Walking Tour - Meeting at 71 East Wacker Drive
Chicago Tours, Ghost & Haunted History Tours, Tour Reviews, Tours, Walking Tours, Walking Tours in Chicago

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 Al Capone stories, haunted hotels, Death Alley, Millennium Park, and the Riverwalk on a lively 2-hour walk.

“We had been walking the same area but knowing the history definitely made our trip more interesting. Sophia was great! Congrats on getting engaged Sophia!”

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Chicago Favorites Ultimate Food and Walking Tour - The Chicago hot dog at Relish
Chicago Tours, Food, Food & Drink, Tour Reviews, Tours, Walking Tours, Walking Tours in Chicago

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 walking Chicago landmarks, with a free bike or kayak rental included.

“Very fun tour full of delicious food. Great portions and a nice variety. Walking was just right in between stops to digest! Had two young teens with us and they enjoyed the tour as well. Would recommend!”

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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 in a Day: Food, History & Architecture Walking Tour - Starting under the Chicago Theatre marquee
Chicago Tours, Food, Food & Drink, Historical Tours, Tour Reviews, Tours, Walking Tours, Walking Tours in Chicago

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, Italian beef, and Chicago hot dogs while exploring the Loop, Riverwalk, Millennium Park, and landmark architecture.

“Dash was fantastic! He loves the City and showed us hidden treasures I’d never seen after traveling to Chicago for nearly 25 years. He pointed us to a list of his favorite off the beaten track finds, so I’d say START your stay in Chicago with this tour. You will NOT be disappointed. He took into account food needs for all. Also, I was having some medical issues I didn’t know about. It resulted in me struggling with the stairs and uphills more than usual. Appreciated that he keyed in and could see I was having some challenges and worked around them, without making a deal of it. Great guide!!!!…”

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