Your insider's guide to the best things to do, see, and experience in Chicago.
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 – It’s a day for love, and there’s few places like being in the Loop to keep your romance alive. Celebrate love with intimate and enjoyable experiences downtown.
5 MIN READ – Chicago Theatre Week (CTW) has become a staple in the city, especially in the Loop’s theatre district, and returns for its 13th year, February 6-16, 2025.
3 MIN READ — Chicago Loop Alliance (CLA) released its quarter four 2025 State of the Loop report on downtown activity, using a variety of data sources, produced by CLA since July 2020. The report tracks pedestrian and transportation activity, investment, retail, arts and culture, and more.
4 MIN READ — Chicago Loop Alliance (CLA) released its quarter three 2025 State of the Loop report on downtown activity, using a variety of data sources, produced by CLA since July 2020. The report tracks pedestrian and transportation activity, investment, retail, arts and culture, and more.
5 MIN READ — Chicago has once again been crowned the Best Big City in the U.S. in the Condé Nast Traveler Readers’ Choice Awards, one of the most prestigious recognitions a destination can receive. This is the ninth consecutive year Chicago has claimed this title, a streak unprecedented in the awards program’s more than 30-year history.
5 MIN READ: Chicago Loop Alliance (CLA) recently released its quarter two 2025 State of the Loop report on downtown activity, using a variety of data sources, produced by CLA since July 2020.
5 MIN READ — Whether you’re visiting the Loop for NASCAR or you’re a local looking to plan the perfect weekend, we’ve got you covered. From can’t-miss events to traffic updates, here’s everything you need to know about what’s happening in the Loop during NASCAR weekend.
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…
May 23, 2026 | 8:00 PM – 10:00 PM
Cruise from the Chicago Riverwalk to Lake Michigan for skyline views and a 3D-enhanced fireworks show with music and narration.
June 1, 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 20, 2026
MUSIC BY MARK HOLLMANN LYRICS BY MARK HOLLMANN AND JAY REISS BOOK BY ERIN QUINN PURCELL AND JAY REISS DIRECTED…
June 30, 2026
An exciting lineup of outdoor films on Tuesdays this summer.
