Things to do in Chicago

Planning questions about Chicago

What are the best things to do in Chicago?

Original Chicago Architecture Interiors Tour: Dazzling Interiors is the highest ranked experience in Chicago, scoring 97 out of 100 on the Outty Ranking from 1,863 traveler reviews. Chicago Favorites Ultimate Food and Walking Tour, Chicago Murder Mystery Tour, Chicago River 90-Minute Architecture Boat Tour, Chicago Architecture and True Crime: Halloween Edition round out the top five. Outty ranks 566 bookable experiences in Chicago, United States, and 4 of them score 90 or above.

Which attractions should I visit in Chicago?

The landmarks with the deepest choice of tours and tickets are Millennium Park, Navy Pier, Grant Park, The Magnificent Mile, Chicago River, Art Institute of Chicago. Each has its own page on Outty listing every ranked way to visit, from timed entry tickets to guided and combination tours.

How much do activities in Chicago cost?

The median price across everything we rank in Chicago is $46 per person, and the cheapest starting price is $10 on Chicago Loop Self-Guided Audio Tour: Architecture & History Walk. Guided, small-group and skip-the-line versions sit above the median, and peak weekends price higher than midweek mornings.

Can I book something in Chicago for today?

Yes. 120 of the top 120 experiences we rank in Chicago currently show same-day availability. Same-day slots are limited, so book early in the day where you can.

Is Chicago good for families?

Yes. 23 of the experiences we rank in Chicago are family friendly, covering short, low-cost activities as well as full-day outings. Check the minimum age on each experience page before booking.

How many days do you need in Chicago?

Three full days covers the headline sights without sprinting: one anchor experience each morning, an unhurried afternoon in a single neighborhood, then a food or nightlife booking in the evening. Five days lets you add a day trip outside the city.

When is the best time to visit Chicago?

May to October. Winter cruises stop running when the river ices. Prices and queues climb in peak weeks, while shoulder season gives you better availability on the top-ranked experiences and more room to change plans.

Can I cancel a booking in Chicago?

116 of the 120 experiences we rank in Chicago offer free cancellation, usually up to 24 hours before the start time. The exact window is shown on each experience page before you book.

How does the Outty Ranking work?

Every experience in Chicago gets a single 0 to 100 score built from traveler sentiment, the depth of review evidence, recent booking momentum, price fairness against comparable options in the same city, operator standing and cancellation flexibility. Scores are benchmarked within Chicago so a strong local option is not buried by global volume, and anything at 90 or above joins the Outty 90+ Club.