5 best things to do in Chicago
The essentials of Chicago with the booking notes that actually matter — which tickets sell out, which slots are quietest, which formats reward the advance purchase. Every booking happens with the provider you choose.
Browse all Chicago activities
Attractions, tours, day trips and transport passes from major providers — instant mobile tickets.
The Chicago shortlist
- Art Institute of Chicago — the American Gothic and Nighthawks museum; Thursdays run late.
- Chicago Architecture Foundation river cruise — the definitive city tour — book the 90-minute boat.
- Skydeck or 360 Chicago — the Willis ledge vs the Hancock tilt; sunset slots book out.
- Deep-dish pizza crawl — the pan pizza and its tavern-style rival; order 45 minutes ahead.
- Millennium Park & the Bean — free, and the mirrored bean is the obligatory photograph.
Flying in, Chicago O'Hare International Airport (ORD) is the main of Chicago's 2 airports — attraction districts sit 30–60 minutes away at typical city speeds.
Compare Chicago activity providers
- Klook — Chicago activities — the widest catalogue, instant QR tickets, strong on transport passes and day trips.
- KKday — Chicago experiences — local-led formats and small-group tours.
- Tiqets — museums and landmarks with instant mobile entry.
Frequently asked questions
What is the number one thing to do in Chicago?
Art Institute of Chicago — the American Gothic and Nighthawks museum; Thursdays run late. Start there, then build the itinerary around it.
Do I need to book Chicago attractions in advance?
The headline attractions reward advance booking — timed-entry systems and quota tickets mean walk-up availability is worst exactly when you want to visit. Everything on this page links to providers showing live availability.
How many days do you need in Chicago?
Three to four days covers the shortlist above at a humane pace for a first visit; add days for the day-trip formats rather than compressing the city itself.
Is a city pass worth it in Chicago?
Run the arithmetic honestly: a pass wins when you would genuinely visit three-plus ticketed attractions in its window. Our provider links show pass options side by side with single tickets — compare before committing.