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.