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 2025 State of the Loop report on downtown activity, using a variety of data sources, produced by CLA since July 2020.
3 MIN READ — On July 19, My Block, My Hood, My City (MBMHMC) will host Downtown Day, a citywide event, aimed at bringing nearly 1,500 youth to downtown Chicago in an effort to expose Chicago teens to the dynamic opportunities of the Loop and downtown area. Over 30 downtown businesses will offer free or discounted attractions; intimate workshops; tours and culinary experiences.
Ride Metra free on all lines to and from the Cadillac Palace Theatre with your show ticket, valid on the date of your performance only.
5 MIN READ– Broadway in Chicago is thrilled to announce the upcoming season lineup. Featuring Rodgers & Hammerstein’s critically acclaimed The Sound of Music, 13-time Tony Award® nominated musical Hell’s Kitchen, the modern-day holiday hit Elf the Musical, the most Tony Award® winning Best Play (2024) Stereophonic, Tony Award® Winner of Best Musical (2024) The Outsiders, and a sixth show to be announced.
7 MIN READ — The Chicago Human Rhythm Project (CHRP) will present its two signature festivals, Stomping Grounds and the 35th Anniversary Rhythm World, as well as its annual Gala! Jubalee honoring Jumaane Taylor, Nora Daley and Alderman Michelle Harris which will support the Mayfair Arts Center capital campaign.
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.
Workbox, a national workspace operator dedicated to providing solutions and resources to growing businesses, opened its largest U.S. location in the Loop neighborhood of Chicago.
3 MIN READ – Take your dad for a day out in the town, downtown to be more specific! Enjoy some iconic Chicago events downtown on Father’s Day, cruise on a boat ride, go to dinner, play darts or pingpong, or shop for gifts. Make the day memorable and celebrate Father’s day in 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
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 4, 2026 "The Goodman premieres The 7 Fingers' "The Attic Things I’ve Seen While Lying On…
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…
