Your insider's guide to the best things to do, see, and experience in Chicago.
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.
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.
6 MIN READ – It’s a day for love, and there’s few places like being in the Loop to keep your romance alive. Celebrate love with intimate and enjoyable experiences downtown.
4 MIN READ – Choose Chicago has announced the restaurants and menus of the 18th annual Chicago Restaurant Week taking place from Friday, January 24 to Sunday, February 9, 2025.
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 by the end of 2025. Here’s a sneak peek at what’s coming soon to the heart of Chicago.
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.
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.
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.
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
Experience Chicago at night on a 90-minute river and lake cruise, featuring a glittering skyline, cool breezes, and lively, family-friendly commentary.
April 17, 2026
Chicago River & Lake Michigan cruise with skyline views, iconic landmarks, and engaging guides sharing the city’s history and stories.
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.
July 7, 2026
BEHIND EVERY POWERFUL WOMAN… ARE MORE POWERFUL WOMEN.
