Chicago, United States

Things to do in Chicago

Architecture on the river, deep-dish on the block

Chicago's signature experience is still the architecture boat cruise, and the difference between the docent-led originals and the party-boat imitators is the single biggest quality gap in the city. Beyond the river: gangster history walks, Art Institute access, deep-dish and hot-dog crawls, and skydeck timed entry. Outty Ranking leans on guide credentials and how consistently the promised route runs.

Ranked activities
120
In the 90+ Club
0
Best time to visit
May to October. Winter cruises stop running when the river ices.

Most Popular in Chicago

The experiences travellers book most right now.

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Most Highly Reviewed in Chicago

Highest traveller sentiment with enough reviews to trust it.

Last Minute in Chicago

Confirmed availability today or tomorrow.

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Family Friendly in Chicago

Works with children in tow, by age policy and pacing.

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Food & Drink in Chicago

Food tours, tastings, markets and dinner experiences.

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Culture & History in Chicago

Museums, landmarks and stories behind the streets.

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Outdoors in Chicago

Fresh air, water, trails and skyline views.

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Nightlife in Chicago

After dark: bars, shows and evening cruises.

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Planning questions about Chicago

What is the highest-ranked activity in Chicago?
Original Chicago Architecture Interiors Tour: Dazzling Interiors, with an Outty Ranking of 85.
When should I visit Chicago?
May to October. Winter cruises stop running when the river ices.
Can I book something for today?
120 of the 120 experiences we rank in Chicago currently show same-day availability.