Your insider's guide to the best things to do, see, and experience in Chicago.
5 MIN READ — Chicago Loop Alliance (CLA) recently released its quarter two 2026 State of the Loop report. CLA has produced reports on downtown activity since July 2020, using a variety of data sources, tracking pedestrian and transportation activity, investment, retail, arts and culture, and more. View the quarter two (Apr.-June 2026) State 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.
5 MIN READ — Summertime Chi is here and we have so many ideas for how to spend it in the Loop this July. The best part? All of these events are FREE. Read more to get ideas for how you can spend your July in the Loop! Get Active Every Saturday now through September …
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.
5 MIN READ — Celebrating its 101st season, Goodman Theatre announces 12 productions in the 2026-2027 programming. From the genre- defying the 7 Fingers to Green Day’s generation-defining hit musical. Read the full lineup below. In the Albert Theatre (856 -seat proscenium stage) The Attic September 5 – October 5 | A World Premiere From …
Chicago’s legendary food festival returns to Grant Park July 8-12, with five days of free concerts, diverse local cuisine and family-friendly programming along the iconic lakefront. Read the full details here.
5 MIN READ — This month for our People of the Loop series, we caught up with Alex Linardos — better known to many as “Mr. South Loop.” The Chicago-based content creator took us around the Loop to share his favorite hidden gems, insider tips, and what makes downtown Chicago such a special place to live, work, and explore. From local recommendations to his perspective on the neighborhood’s energy and growth, Alex gives an inside look at why the Loop continues to inspire him. Read the full Q&A below, and don’t forget to check out the video feature on our social channels.
5 MIN READ — The Chicago Department of Cultural Affairs and Special Events (DCASE) announces the return of the Millenium Park Summer Workouts, Summer Music Series and Summer Film Series. Running May through August, these signature free programs bring world-class performances, fan-favorite films and energizing fitness experiences all in the heart of the Loop.
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
Experience Chicago at night on a 90-minute river and lake cruise, featuring a glittering skyline, cool breezes, and lively, family-friendly commentary.
April 17, 2026
Chicago River & Lake Michigan cruise with skyline views, iconic landmarks, and engaging guides sharing the city’s history and stories.
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.
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.
