Your insider's guide to the best things to do, see, and experience in Chicago.
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.
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.
2 MIN READ – Go down rainbow road and celebrate the LGBTQ community in the Chicago Loop this summer. Food and drink specials, drag brunch, a music festival, and more are in store.
2 MIN READ – Memorial Day weekend is a time to honor those who have served and sacrificed for our country. It also marks the start of summertime activities in the city! There are plenty of things to do in the Loop this Memorial Day weekend, and we’ve rounded up your best options.
5 MIN READ – Celebrate this Mother’s Day in the Loop. Go out to brunch and drink specialty cocktails. Appreciate the spring weather with a boat ride on the Chicago River. For a scenic view, dine at a rooftop bar. To relax, rejuvenate at the spa. Give gifts, sweet treats, and floral arrangements. Regardless of how you spend your day downtown in the Loop, you will bond with Mom, and that’s all that matters.
What if the world you thought you knew wasn’t real? That question takes center stage in The Space in Between, where those who encounter truth must decide: Will I step forward into reality, or will I retreat into the comfort of illusion.
5 MIN READ: The Chicago National Landmark formerly known as The Auditorium Theatre, unveils a new identity as The Auditorium. The Auditorium also released their 2025-2026 dance season Celebrating Women Leaders in Dance. This season will showcase Five Female-led companies breaking barriers and paving the way for future dance generations. Featuring Tyler Peck and Friends, Ensemble Español Spanish Dance Theater, Martha Grahm Dance Company, Trinity Irish Dance Company and Alvin Ailey American Dance Theatre.
2 MIN READ – Hop into the Chicago Loop this Easter and Passover season for an egg-cellent adventure with your friends and family! With plenty of egg-citing events and activities, you’re sure to have an un-bunny-lievable time.
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…
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.
August 26, 2026 | 5:00 PM – 7:00 PM
Taste of Greektown comes early to Renaissance! Featuring a special evening celebrating local Mediterranean heritage with an artisanal mezze spread…
