Your insider's guide to the best things to do, see, and experience in Chicago.
3 MIN READ – It’s time once again to usher in a new year, and there’s no better place to do it than downtown in the Chicago Loop. Glitzy and glamorous open bar events await, along with live music, immersive experiences, and more.
2 MIN READ – Check all the gifts off of your shopping list, and then treat yourself to world-class attractions and entertainment.
Create lasting memories with the whole family downtown at the Loop’s must-see holiday destinations.
2 MIN READ – Rather than being upset that another Chicago summer is over, prepare your favorite costume for a month of spooktacular Halloween festivities in the Chicago Loop. See our top picks for events and more below.
5 MIN READ – For many, Labor Day offers one last three-day weekend to enjoy summertime weather, so you’d better make the most of it! Spend the day in the Chicago Loop enjoying major events, great outdoor public space, world-class museums, delicious dining, an iconic shopping district, and more. If you’re having way too much fun, turn it into a vacation with an overnight stay in one of the Loop’s luxurious hotels. No matter what you’re into, the Loop’s got you covered.
4 MIN READ – Fall in love with your city all over again with this guide from the locals. Whether you want to sit back and relax or go on many active adventures, in the Chicago Loop, the possibilities are endless.
4 MIN READ – NASCAR Chicago Street Race announced that it will partner with Chicago Loop Alliance and JoRand (founded by local restauranteurs Victor Love and Mark Rand) to expand this year’s NASCAR Village, the free, public experience in Butler Field throughout race weekend.
3 MIN READ — Juneteenth has long been celebrated by Black Americans across the country, including in Chicago. Officially declared a national holiday in 2021, the day marks the date when the news of the Emancipation Proclamation reached enslaved Blacks in Galveston, Texas on June 19, 1865. Chicago is built on the innovation and legacy of many Black people including Jean Baptiste Point Du Sable, Ida B. Wells, Gwendolyn Brooks, Harold Washington and many more. Commemorate the longest-running Black holiday 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…
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.
