5 Best Chicago Walking Tours

The ones worth booking.

The 5 chicago walking tours travellers book the most. We walk you through what each one covers on the ground, who guides it and what it costs, so you can pick the right one before you lace up.

5 Best Chicago Walking Tours

Chicago, Chicago Walking Tours, Ghost & Dark History Walks, Tour Reviews, Tours, True Crime & Mafia Walks, Walking Tours

Chicago: Gangsters and Ghosts Walking Tour

/ June 16, 2026

1.Chicago: Gangsters and Ghosts Walking Tour

Prohibition-era gangster tales and ghost stories across Chicago’s Loop, haunted hotels, and Millennium Park. Historian guide.

Chicago Favorites Ultimate Food and Walking Tour

/ June 16, 2026

2.Chicago Favorites Ultimate Food and Walking Tour

Taste classic Chicago staples on a 3-hour Loop walk with generous bites, Millennium Park sights, and a free bike or kayak add-on.

★ 5.0

“AJ did an amazing job not only bringing us to some amazing food but also telling us about the history of the city as we went, we learned so much we otherwise may have never learned!”

1,962 reviews3 hours (approx.)From $84.99by Bobby's Bike, Hike & Food Tours - Chicago

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Chicago, Chicago Walking Tours, Ghost & Dark History Walks, Guided, Tour Reviews, Tours, True Crime & Mafia Walks, Walking Tours

Chicago: Gangsters and Ghosts Guided Walking Tour

/ June 16, 2026

3.Chicago: Gangsters and Ghosts Guided Walking Tour

Historian-led Chicago South Loop walk mixes gangster legend and ghost lore, with hotel interiors, Death Alley, and the Congress Hotel.

★ 4.7

1,697 reviews2 hoursFrom $36by Empire Tours & Productions (Chicago Gangsters and Ghosts Tours)

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Chicago, Chicago Walking Tours, Hidden Gems & Local Walks, Tour Reviews, Tours, Walking Tours

Chicago’s Secret Interiors Architectural Walking Tour

/ July 28, 2026

4.Chicago’s Secret Interiors Architectural Walking Tour

Chicago’s Secret Interiors walking tour with rare access to landmark lobbies, mosaics, and gardens for about two hours.

★ 5.0

“Grant was an extremely warm, knowledgeable and organized tour guide. He seamlessly lead a group of 15-20 of us from building to building. It was a very cold day but we do spend a good amount of time indoors so the weather felt really manageable. It was really cool tRead more”

635 reviewsFrom $35by Chicago River Boat Architecture Tours

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