Your insider's guide to the best things to do, see, and experience in Chicago.
5-MINUTE READ — Looking for ways to make the most of September? Fall is here, and there’s no better place to experience the season than the Loop. From festivals and live performances to cultural experiences and more, we’ve rounded up some of the best ways to explore, experience, and enjoy the Loop this month. September …
5 MIN READ — The Weather Bell has been a long-standing landmark in the Loop for 75 years. Now it’s being restored for a different era. So, what is the Loop Weather Bell, and what makes it so iconic? On the northwest corner of the Rector Building at 79 W. Monroe sits the iconic weather …
5 MINUTE READ — Meet Tom Liravongsa, better known as The Skyscraper Guy, and discover how he’s helping restore Chicago’s iconic Pittsfield Building while sharing the stories that keep the city’s architectural history alive. From Medical Offices to Modern Living The Pittsfield Building, one of Chicago’s most iconic skyscrapers, is entering a new and exciting …
5 MIN READ — Big things are on the horizon for the Loop! From brand-new storefronts to exciting expansions, a wave of businesses is set to open their doors. Here’s a sneak peek at what’s coming soon to the heart of Chicago in 2026.
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.
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…
