The Best Things to Do in Chicago, Ranked
Chicago's top-rated experiences in one list — from the architecture river cruise and Skydeck to the Art Institute and a deep-dish food night, ordered by real traveller review scores.
Available
15 options
Avg. rating
4.7 - 24,309 reviews
From
$17 USD
Cancellation
Free up to 24h before
Best Things to Do: what to know before booking
Chicago's top-rated experiences in one list — from the architecture river cruise and Skydeck to the Art Institute and a deep-dish food night, ordered by real traveller review scores.
- Availability
- 15 ticket options compared
- Starting price
- Tickets currently start around $17 USD before checkout fees.
- Rating signal
- Compared options average 4.7 stars across 24,309 traveler reviews.
- Location
- Across downtown Chicago — most sit within the Loop, the Riverwalk, the Magnificent Mile, and the lakefront Museum Campus
- Best time
- Late spring through early fall for cruising; book deck tickets for the hour before sunset
- Ticket note
- Most are date- or time-stamped; check each booking
Best Things to Do in Chicago
Sorted by review signal, price, and availability. Tap any card to book through the provider checkout.
Everything you should know before you book
Chicago is a city built on big-shouldered architecture, world-class art, a vast lakefront, and a food scene that goes far beyond deep-dish. This ranking pulls the city's highest-rated bookable experiences so you can build a shortlist fast — the architecture river cruise, both observation decks, the Art Institute and Field Museum, lake cruises, and the food tours are all here.
Book the marquee tickets ahead. The Skydeck, 360 Chicago, and the architecture river cruise all run timed entry or fixed sailings, and summer weekend slots go first. Everything below is bookable with instant confirmation and, on most options, free cancellation. If you'll do three or more big attractions, a Chicago CityPASS or Explorer Pass bundles the decks, museums, and a cruise for less.
Frequently asked questions
What is the number one thing to do in Chicago?
The architecture river cruise is the essential first stop — it's the best primer on the skyline. The Skydeck, the Art Institute, and a deep-dish food tour round out the classic Chicago line-up. This list ranks them all by traveller reviews.
How many days do you need in Chicago?
Two days covers the highlights — the architecture cruise, a museum, both decks, and the food. Three lets you add the Field Museum, Chinatown, and the lakefront. See our 2- and 3-day Chicago itineraries.
Is a Chicago attraction pass worth it?
If you'll visit three or more big sights, a CityPASS or Explorer Pass bundles the decks, museums, and a cruise for less than buying separately. For one or two attractions, individual tickets are usually cheaper.