Your insider's guide to the best things to do, see, and experience in Chicago.
5-MINUTE READ — Fall has arrived in the Loop, bringing a fresh lineup of ways to experience downtown Chicago. As the season changes, the neighborhood comes alive with art, culture, entertainment and plenty of reasons to get out and explore. From new experiences to annual fall favorites, here’s your guide to making the most of …
5 MIN READ – One of the nation’s largest music festivals, Lollapalooza, takes place July 30-August 2, 2026, in the Chicago Loop. This year’s lineup includes Charli XCX, Olivia Dean, John Summit, Lorde, Jennie, The XX and more. Here is everything you need to know.
6 MIN READ – Summers are fleeting in Chicago, only to give way to our brutal winters, so get out and enjoy the weather while it lasts. Do everything on your summer bucket list, like listening to live music, going on a bike ride, swimming, seeing art at a museum, and visiting the Chicago Loop’s best attractions while it’s still warm.
March 15, 2026
Chicago’s top-rated architecture boat tour, 90 minutes with expert CAC guides, stunning skyline views, open-air seating, and onboard amenities.
March 21, 2026
Explore Chicago’s haunted past on a nighttime river cruise featuring ghost stories, mob history, and eerie secrets of the Windy City.
April 17, 2026
Chicago River & Lake Michigan cruise with skyline views, iconic landmarks, and engaging guides sharing the city’s history and stories.
April 17, 2026
Experience Chicago at night on a 90-minute river and lake cruise, featuring a glittering skyline, cool breezes, and lively, family-friendly commentary.
April 22, 2026
Directed by Andrew Scoville. Co-created by Academy, Grammy, and Tony Award-winning artist David Byrne* and writer Mala Gaonkar, Theater of the Mind is a new theatrical…
July 11, 2026
Cruise Chicago’s waterways with your dog. Pet friendly, scenic, and fun. Available July to October every Saturday and Sunday for pups of all sizes.
September 4, 2026
Experience Jaw-Dropping Magic. Enter through the doors at 50 West Randolph to discover a hidden world where the impossible becomes…
September 5, 2026
Sept 5 - Oct 11, 2026 Extended by popular demand through October 11! The Goodman premieres The 7 Fingers "The…
September 8, 2026
Kokandy Productions’ critically acclaimed revival of the 10-time 2025 Jeff Award–nominated musical JEKYLL & HYDE will make its Broadway In Chicago debut at the Broadway Playhouse…
