History walks in Chicago
Guided walks through old towns, wartime districts and ancient centres, led by guides who know what happened on each street.
Advertising disclosure: tour links go to Viator. If you book through one, we may earn a commission at no extra cost to you. Every tour here is rated 4.5 stars or more by travellers on Viator.
Compare at a glance
Prices run from £27 to £77 per person. 2 of 3 are private or small-group tours (12 people or fewer). Select a tour name for meeting point, stops and what's included.
| Tour | Duration | Group | From | Rating |
|---|---|---|---|---|
| Chicago in a Day Walking Tour: Food, History & Architecture | 4.5 hours | Up to 12 | £77 | 4.9 (1,457) |
| Chicago Walking Tour: Historic Treasures of Chicago | 2 hours | Up to 15 | £27 | 4.9 (457) |
| Walkin' with Colin: Chicago History-Mystery-Comedy-Tragedy Tour | 2 hours | Up to 10 | £34 | 5.0 (256) |
Chicago in a Day Walking Tour: Food, History & Architecture (opens Viator in a new tab)
A four-and-a-half-hour walk combining Chicago's food, history and architecture. Tour details: Chicago in a Day Walking Tour: Food, History & Architecture
Guided in English
From £77Free cancellation
See dates & bookBooked securely on Viator
Chicago Walking Tour: Historic Treasures of Chicago (opens Viator in a new tab)
A walk past the landmark buildings of Michigan Avenue and State Street from Chicago's architectural golden age. Tour details: Chicago Walking Tour: Historic Treasures of Chicago
Guided in English
From £27Free cancellation
See dates & bookBooked securely on Viator
Walkin' with Colin: Chicago History-Mystery-Comedy-Tragedy Tour (opens Viator in a new tab)
A comic walk through Chicago's history, mysteries and tragedies. Tour details: Walkin' with Colin: Chicago History-Mystery-Comedy-Tragedy Tour
Guided in English
From £34Free cancellation
See dates & bookBooked securely on Viator
Prices are Viator's lowest "from" price per person, converted to pounds and checked on 28 October 2026. The booking page shows the current price in your currency.
More history walks on GetYourGuide
GetYourGuide sells many of the same walks and some that Viator doesn't. Their list for Chicago is chosen and ranked by GetYourGuide, not by us.
Search Chicago on GetYourGuide (opens in a new tab)
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More for walkers in Chicago
- Chicago walking guide: sights, neighbourhoods, when to visit and all 13 guided walks.
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