Your insider's guide to the best things to do, see, and experience in Chicago.
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.
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.
Want to know where to go for Cinco de Mayo? The Chicago Loop has fantastic specials for the celebration of the May 5 holiday honoring the Mexican army’s victory over France at the battle of Puebla in 1862. Sneak in a siesta before you fiesta, and enjoy some of the hottest deals in town.
3 MIN READ – Take your night to a whole new level at one of the Chicago Loop’s finest rooftop bars, offering some of the best views in the city.
3 MIN READ — Chicago Loop Alliance (CLA) recently released its quarter one 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.
2 MIN READ — Chicago Loop Alliance (CLA) announced its new President and CEO, Suzet McKinney. Her career spans public health, public safety, real estate, corporate, tech and government sectors and will provide strategic implementation in expanding the organization’s impact, increasing confidence in the Loop while ensuring it is everyone’s neighborhood, and creating a complete urban district.
3 MIN READ — After work, go out for drinks! Happy hour is happening all throughout the Loop, so you can wind down after a long day. Choose from all these unique venues, each with their own style and atmosphere.
6 MIN READ – When I began creating House on Mango Street, I knew the work had to be rooted in listening. Not just to the text, but to the lives and memories that surround it. I was not interested in a literal translation of Sandra Cisneros’s stories. I wanted to understand the world that shaped them and the ways those stories continue to live in the body.
marzo 15, 2026
Chicago’s top-rated architecture boat tour, 90 minutes with expert CAC guides, stunning skyline views, open-air seating, and onboard amenities.
marzo 21, 2026
Explore Chicago’s haunted past on a nighttime river cruise featuring ghost stories, mob history, and eerie secrets of the Windy City.
abril 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.
abril 17, 2026
Chicago River & Lake Michigan cruise with skyline views, iconic landmarks, and engaging guides sharing the city’s history and stories.
mayo 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.
junio 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…
junio 30, 2026
An exciting lineup of outdoor films on Tuesdays this summer.
julio 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.
julio 17, 2026
Extended by popular demand through August 2! The Goodman presents Raven Theatre's production of OCTET Music, Lyrics, Book and Vocal…
