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Best Things to do in Chicago (2026)

Many of the best experiences in Chicago are outdoors and free. The Chicago Riverwalk runs along the south bank of the river through the Loop, with places to eat and drink and docks for cruises and water taxis, and it is the easiest way to see the downtown towers up close. Further north and west, The 606 follows a former railway line for 2.7 miles above the streets of Logan Square, Humboldt Park and West Town, and it is used for walking, running and cycling.

For a classic Chicago evening, book a show at The Second City in Old Town, the comedy theatre founded in 1959 whose alumni include many famous names. Sports fans should plan around Wrigley Field, home of the Cubs since 1916, either for a game in season or a guided tour of the ballpark. For a view with a drink, 360 Chicago on the 94th floor of 875 North Michigan Avenue is open until 11pm, with the TILT ride for those who want a thrill. Booking ahead is wise for shows, tours and weekend visits.

5 places · Updated October 27, 2026

Our top 3 things to do in Chicago

  1. Chicago Riverwalk Riverside promenade, The LoopThe Chicago Riverwalk runs along the south bank of the river's main branch through the Loop, with plazas, piers, floating gardens, places to eat and boat departures.
  2. 360 Chicago Observation deck and TILT ride, Streeterville360 Chicago is the 94th-floor observation deck in the former John Hancock Center, about 1,030 feet up, with the TILT ride and the CloudBar.
  3. The Second City Comedy and improv theatre, Old TownFounded in 1959, The Second City is Chicago's famous sketch and improv comedy theatre in Old Town, with shows on its Mainstage, e.t.c. stage and UP Comedy Club.

Thing to do

1. Chicago Riverwalk

Riverside promenadeThe Loop

The Chicago Riverwalk runs along the south bank of the river's main branch through the Loop, with plazas, piers, floating gardens, places to eat and boat departures.

View details — Chicago Riverwalk

Thing to do

2. 360 Chicago

Observation deck and TILT rideStreeterville

360 Chicago is the 94th-floor observation deck in the former John Hancock Center, about 1,030 feet up, with the TILT ride and the CloudBar.

View details — 360 Chicago

Thing to do

3. The Second City

Comedy and improv theatreOld Town

Founded in 1959, The Second City is Chicago's famous sketch and improv comedy theatre in Old Town, with shows on its Mainstage, e.t.c. stage and UP Comedy Club.

View details — The Second City

Thing to do

4. Wrigley Field

Historic baseball stadium and toursWrigleyville

Wrigley Field, home of the Chicago Cubs since 1916, is a 1914 ballpark in Wrigleyville with ivy-covered walls, a hand-turned scoreboard and guided tours.

View details — Wrigley Field