5-MINUTE READ — Fall has arrived in the Loop, bringing a fresh lineup of ways to experience downtown Chicago. As the season changes, the neighborhood comes alive with art, culture, entertainment and plenty of reasons to get out and explore. From new experiences to annual fall favorites, here’s your guide to making the most of the season in the Chicago Loop.
October Fairs & Festivals
Chicago Art Fair at THE MART
October 7–10 | THE MART
Making its debut at THE MART this October, Chicago Art Fair brings together artists, galleries, collectors and art enthusiasts for four days of contemporary and modern art.
Visitors can explore a curated selection of artwork from leading galleries, discover special projects, and find new artists and works to add to their collections.
Spectrum Chicago at THE MART
October 7–10 | THE MART
Spectrum Chicago is a new contemporary art fair showcasing original works by emerging and established independent artists from across the country and around the world.
Attendees can discover and collect artwork, connect directly with artists and experience a diverse range of creative perspectives in an accessible setting.
Loop Arts Fest
Saturday, October 17 | 12–6 p.m. | State Street
Celebrate the arts and culture of downtown Chicago at Loop Arts Fest, a free, day-long street festival presented by Chicago Loop Alliance. State Street will close to vehicular traffic between Jackson Boulevard and Madison Street as artists, performers, cultural organizations, and local businesses come together for a celebration of the Loop’s vibrant creative community. The festival will feature on-street activations alongside additional arts and cultural programming happening throughout the Loop.
Open House Chicago
October 17–18 | Locations throughout Chicago
Go behind the scenes at Open House Chicago, the Chicago Architecture Center’s annual celebration of architecture, design, and the city’s built environment. This free public festival gives visitors access to more than 200 sites across Chicago, including many locations that are not typically open to the public. This year, 33 participating locations are in the Loop and downtown Chicago, making it an ideal weekend to explore the neighborhood from a new perspective.
As part of Loop Arts Fest’s off-site programming, The Joffrey Ballet will also welcome visitors for an open rehearsal viewing, giving guests a behind-the-scenes look at the creative process. More details on the Loop Arts Fest program and participating locations are coming soon.
Spooky + Halloween-Themed Experiences
Medieval Torture Museum
Daily | 10 a.m.–8 p.m. Monday–Thursday; 10 a.m.–9 p.m. Friday–Sunday
Looking for a Halloween experience that goes beyond the typical haunted house? Step back in time at the Medieval Torture Museum, where a collection of historical torture devices and immersive exhibits explore some of the darker chapters of human history. Combining historical research with a chilling presentation, the museum offers a fascinating—and unsettling—experience that’s especially fitting for a fall visit. Are you brave enough to explore it?
Halloween Creepy Cruise
Select dates through November 1 | Fridays, Saturdays and select Thursdays and Sundays
Take your Halloween adventure to the water aboard the Creepy Cruise presented by First Lady Cruises. Cruising through Chicago from March through November, this spooky sightseeing experience combines the city’s history with chilling stories and eerie tales about the secrets lurking beneath the surface of the Windy City. Set against the Chicago skyline and river, it’s a unique way to experience the city this fall—if you’re brave enough.
