Your insider's guide to the best things to do, see, and experience in Chicago.
3 MIN READ – The Hustle Chicago® stair climb returns to the former Hancock Building on February 22, 2026, and brings thousands of participants together to take on 94 floors in support of lung health and clean air.
2 MINUTE READ — Ring in the New Year in the heart of Chicago! The Loop comes alive with dazzling celebrations—from iconic citywide spectacles to intimate cultural events—offering something for every kind of reveler. Whether you’re looking for free community festivities, live performances, riverfront fireworks, or ticketed parties with a view, the Loop is the place to be as we count down to 2026.
As the air cools and leaves begin to change, First Lady invites locals and visitors to experience fall in Chicago from the water. Now through November, guests can enjoy crisp breezes, glowing sunsets, and stunning skyline views aboard a variety of sightseeing and specialty cruises.
5 MIN READ — Crisp air, cozy sweaters, and vibrant colors mean one thing—fall has arrived in Chicago! From festive riverfront celebrations and pumpkin patches to colorful Halloween experiences and seasonal treats, the city is buzzing with ways to soak in the season. This guide is your go-to for the best fall happenings in the Chicago Loop—perfect for family outings, date nights, or a fun day with friends.
2 MIN READ – There are many ways you can honor and celebrate Hispanic Heritage Month, which takes place September 15 through October 15. Here are a few ways you can support and uplift Hispanic arts & culture in the Loop!
2 MIN READ: The Christkindlmarket is delighted to announce the return of its cherished holiday tradition for its 29th season at Daley Plaza in Chicago, with new special activations.
3 MIN READ – There’s nothing quite like it. One of the nation’s largest music festival, Lollapalooza, takes place July 31- August 3 in the Chicago Loop, and this year’s lineup lineup includes Tyler the Creator, Olivia Rodrigo, Twice, Sabrina Carpenter, A$AP Rocky, and many more.
5 MIN READ — Chicago Loop Alliance announced the full lineup of artists and activations for Sundays on State. The internationally acclaimed, award-winning event series closes the most iconic parts of State Street in the Loop to vehicle traffic for two Sundays this fall. Free and open to the public, this year’s events will take …
March 14, 2026
Chicago’s top-rated architecture boat tour, 90 minutes with expert CAC guides, stunning skyline views, open-air seating, and onboard amenities.
March 20, 2026
Explore Chicago’s haunted past on a nighttime river cruise featuring ghost stories, mob history, and eerie secrets of the Windy City.
April 16, 2026
Chicago River & Lake Michigan cruise with skyline views, iconic landmarks, and engaging guides sharing the city’s history and stories.
April 16, 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 21, 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…
May 23, 2026 | 3:00 PM – 5:00 PM
Cruise from the Chicago Riverwalk to Lake Michigan for skyline views and a 3D-enhanced fireworks show with music and narration.
May 31, 2026
Let your creative potential shine this summer with a class at the School of the Art Institute of Chicago, with options available for kids, teens and…
June 5, 2026
From June 6th until July 5th, the phenomenal Champions of Magic bring their acclaimed illusion spectacular to Chicago. Featuring their biggest illusions ever, experience the Broadway-scale…
June 19, 2026
MUSIC BY MARK HOLLMANNLYRICS BY MARK HOLLMANN AND JAY REISSBOOK BY ERIN QUINN PURCELL AND JAY REISSDIRECTED BY MARC BRUNISTARRING…
