Your insider's guide to the best things to do, see, and experience in Chicago.
2 MIN READ – Cheerful music, winter lights, and foods and gifts from all over the world – that is the Christkindlmarket Chicago. This authentic German-style outdoor market has been around since 1996 and opens its festive doors in the Loop every year mid-November until Christmas Eve.
3 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, specials, and more below.
1 MIN READ – Get a peek at some of the Loop offices – all of which opened or were remodeled in the past couple of years—Crain’s deemed the coolest.
5 MIN READ – If you’re looking for off-the-beaten-path places for original Instagram photos, look no further than the Loop. From iconic or hidden-away public art to world renowned architecture to sky high views and gorgeous public spaces, your grid is about to get upgraded.
4 MIN READ – If you’re coming #BackInTheLoop for the first time since the start of the COVID-19 pandemic, here’s what’s new.
2 MIN READ – Celebrate the Fourth of July holiday weekend in the Chicago Loop. Here are four ways to celebrate without breaking the bank!
2 MIN READ – As office workers continue to come #BackInTheLoop, we know it’s more important than ever to reconnect with colleagues you haven’t seen in years – or never met in person at all Hit up your old favorite spots, or try something new, but get your office outings on the calendar.
2 MIN READ – If you’re itching to get a dose of arts and culture, the Loop is the place to be!
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…
