Want to know what’s happening this weekend in Chicago? Look no further. There’s a whole calendar of exciting events, exhibits, and activities taking place all over the city this month in Chicago.
A few of this weekends highlights include:
- The free Chicago Live Festival at Navy Pier, with Common headlining
- More top music festivals like Riot Fest and Englewood Jazz Festival
- The start of Hispanic Heritage Month celebrations around the city
- Chicago Exhibition Week, featuring 50+ galleries and art spaces
- Free neighborhood walks during International Greeter Day
Check out just a few of the events and happening in Chicago this weekend, Sept. 18 – 20.
International Greeter Day
Celebrate International Greeter Day with free pop-up walks. Start in Millennium Park and head out with a Chicago Greeter to explore neighborhoods all around the city.
No preregistration is required, just show up! Tours depart between 10 and 11:30 a.m.
Chicago Live at Navy Pier
Chicago Live returns to Navy Pier on Saturday, September 19 and Sunday, September 20, 2026, from noon to 6pm each day. Navy Pier bills it…
Reeling: The Chicago LGBTQ+ International Film Festival
Queer people have always been here. We've always created. We've always told stories. And for 44 years, Reeling has helped bring those stories that go…
The 27th Anniversary Englewood Jazz Festival
The 27th Anniversary Englewood Jazz Festival free events to be held September 17-19, 2026 at Hamilton Park, Chicago CELEBRATING YOUNG MUSICIANS OF THE NEXT GENERATION, …
Riot Fest 2026
Daily Lineup Headliners: Friday, September 18: Headlined by Twenty One Pilots, Iggy Pop, Rise Against, and Pixies, with support from Alkaline Trio and The All-American…
Chicago Exhibition Week
During the fourth annual Chicago Exhibition Week, more than 50 galleries and creative spaces will host exhibits, tours, performances, and more during this week-long celebration of the city’s arts scene.
Destinos: Chicago International Latino Theater Festival
The 9th annual Destinos International Latino Theater Festival showcases Latino theatre companies from Chicago and across the country. Choose from a variety of works staged at some of the city’s top independent theatre venues.
Chicago Bears vs. Minnesota Vikings
Come cheer on the Bears during their first home game of the season at iconic Soldier Field.
Annual Lakeview East Festival of the Arts
The Lakeview East Chamber of Commerce is proud to host and produce the 21st Annual Lakeview East Festival of the Arts, along Broadway, from Belmont…
World Dumpling Fest 2026
Ten-plus restaurants, one park, and more dumplings than you can reasonably talk yourself out of trying. World Dumpling Fest is the kind of afternoon where…
The 37th Annual Rhinoceros Theater Festival Returns September 20 – October 26 at Four Chicago Venues
Curious Theatre Branch, with co-producers Chicago Danztheater Ensemble, Chicago Dramatists and Labyrinth Club, are pleased to announce the 37th annual Rhinoceros Theater Festival, September 20…
Retro on Roscoe 2026
Get ready to time-travel at Retro on Roscoe, presented by Wells Fargo, one of Chicago’s most beloved street festivals, happening September 18–20 in charming Roscoe…
Ritmo del Mar at Shedd Aquarium
¡Muévelo! Join us at Shedd Aquarium for the Ritmo del Mar. Enjoy a night of music, cuisine, culture and mesmerizing animals with an aquatic backdrop…
Phoebe Bridgers – The Lost Tour
Phoebe Bridgers will bring her newly announced headline arena run, The Lost Tour, to Chicago on September 18-19, 2026, at the United Center.
Uptown Rhythm Festival
Get Ready for the Uptown Rhythm Festival! Uptown Rhythm Festival is where tradition meets transformation. Join us in Chicago's vibrant Uptown neighborhood for a powerful…
Old Town Oktoberfest on Wells Street
Chicago's historic Old Town neighborhood raises a stein to fall as Old Town Oktoberfest returns September 18–20, 2026. Celebrating the neighborhood's rich German heritage, this…
Chicago Story Fest 2026
The oldest human art form is coming to the big stage. After selling out in SF, Detroit, and Philadelphia, Chicago Story Fest makes its long-awaited…
Creepy Cruise
From strange sightings to eerie haunts, mobsters and more, our latest nighttime tour takes you into Chicago's shadowy past. Cruise along the Chicago River as…
Fall Magnificent Mile Art Festival
Amdur Productions brings the Fall Magnificent Mile Art Festival to the plaza at 875 North Michigan Avenue on Saturday, September 19 and Sunday, September 20,…
Flotsam River Circus
Flotsam River Circus, a troupe of world-class musicians, puppeteers, and circus artists who travel aboard a handmade raft, is bringing its magical floating spectacle to…
Proud and Loud: Disability Art and Music Showcase
Proud and Loud: Disability Art and Music Showcase takes place on Saturday, September 19, 2026, from 11am to 1pm at the Garfield Park Field House,…
Monster Jam
Monster Jam returns to Rosemont, Illinois, for a high-octane weekend from Friday, September 18, 2026, through Sunday, September 20, 2026.
Jekyll& Hyde
Kokandy Productions’ critically acclaimed revival of the 10-time 2025 Jeff Award–nominated musical JEKYLL & HYDE will make its Broadway In Chicago debut at the Broadway Playhouse at…
Tangible Sound: Arrival to a Higher Ground
Imagine walking inside the thunderous sound of a taiko drum or feeling enveloped by the sinuous sounds of a saxophone, cello, or bass. What if…
Explore our events calendar for more Chicago events and happenings.
Please note that all events are subject to change.
