Your insider's guide to the best things to do, see, and experience in Chicago.
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.
5 MIN READ — This month for our People of the Loop series, we caught up with Alex Linardos — better known to many as “Mr. South Loop.” The Chicago-based content creator took us around the Loop to share his favorite hidden gems, insider tips, and what makes downtown Chicago such a special place to live, work, and explore. From local recommendations to his perspective on the neighborhood’s energy and growth, Alex gives an inside look at why the Loop continues to inspire him. Read the full Q&A below, and don’t forget to check out the video feature on our social channels.
3 MIN READ – Classic St. Patrick’s Day activities in the Loop are back in full bloom! From the Chicago River dyeing to the best bars and restaurants, we’ve rounded up the best ways to get your green on for St. Paddy’s.
4 MIN READ – March is all about celebrating the incredible women shaping our world. Join us in honoring their legacy by supporting women-led businesses in and around the Chicago Loop this Women’s History Month.
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.
5 MIN READ – Chicago Theatre Week (CTW) has become a staple in the city, especially in the Loop’s theatre district, and returns for its 13th year, February 6-16, 2025.
3 MIN READ – The beautiful thing about Black history is that it’s still being made every day. Check out what these Loop businesses and organizations have to offer, and find a way to honor Black History Month this February.
3 MIN READ — Chicago Loop Alliance (CLA) released its quarter four 2025 State of the Loop report on downtown activity, using a variety of data sources, produced by CLA since July 2020. The report tracks pedestrian and transportation activity, investment, retail, arts and culture, and more.
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.
