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 multi-venue World Music Festival, with musicians from across the globe
- Chicago Gourmet, an upscale food festival featuring the city’s top chefs
- The 20th annual Hyde Park Jazz Festival, offering free admission
- An array of Hispanic Heritage Month celebrations around the city
Check out just a few of the events and happening in Chicago this weekend, Sept. 25 – 27.
Chicago Gourmet 2026
Chicago Gourmet is back for another incredible year! This year’s theme, “Let Your Tastebuds Dance,” celebrates the shared energy and passion of food and dance.…
2026 Presidents Cup
Witness history as Brandt Snedeker’s U.S. Team looks to retain the Cup against Geoff Ogilvy’s International Team at Medinah Country Club, during the PGA Tour’s premier global event.
Chicago Wellness Week
Chicago Wellness Week September 21–27, 2026 Chicago Wellness Week is a premier citywide wellness festival that transforms Chicago into a destination for health, movement, culture,…
Hyde Park Jazz Festival 2026
The Hyde Park Jazz Festival returns Saturday and Sunday, September 26 and 27, 2026, across multiple Hyde Park venues on Chicago's South Side. The organizer…
Chicago Underground Film Festival
The longest-running underground film festival in the world shines a spotlight on the defiantly independent filmmaker. Screenings cover documentaries, world premieres, and experimental formats.
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…
Fall Fest at Lincoln Park Zoo
Chicago’s favorite free and family-friendly festival is back at Lincoln Park Zoo for another season of harvest-time fun! From September through October, stop by the…
WingOut Chicago 2026
WingOut Chicago | Sept 26-27 | Gallagher Way • Chicago Join us at Gallagher Way in Wrigleyville for Chicago’s most mouth-watering outdoor event of the…
Randolph Street Market
Joining other world-class cities, including Paris, London, LA, and New York, Chicago’s Randolph Street Market is a key market event destination that locals and fans…
Czech Heritage Week
The 3rd annual Czech Heritage Week will showcase the richness of Czech culture in Chicago. This year’s festival will offer an exceptionally diverse array of events—ranging from classical music and theater to film screenings and historical lectures, as well as folklore celebrations and traditional cuisine.
NHL Preseason: Chicago Blackhawks vs. St. Louis Blues
Come cheer on the Blackhawks!
Top Gun: Maverick In Concert
Top Gun: Maverick was nominated for six Academy Awards® including Best Picture and Best Original Song, winning Best Sound. After more than 30 years of…
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.
Sabor Fest
Sabor Fest returns to 18th & Halsted in Pilsen September 25–27, bringing local businesses, food, music, and culture together for a weekend rooted in the…
Meet Me on Milwaukee (MMoM)
Meet Me on Milwaukee (MMoM) is a pilot series of “pedestrianization” events between Alderman La Spata, the Wicker Park Bucktown Chamber of Commerce (WPBCC), and the…
Chicago Humanities Fall Festival Pilsen Day 2026
Chicago Humanities Fall Festival’s Pilsen Day on Saturday, Sept. 26 takes place at the National Museum of Mexican Art and Thalia Hall and features an…
13th Annual Beverly Art Walk
Artists, venues, performers, and patrons are gearing up for the 13th annual Beverly Art Walk on Saturday, Sept. 26, 11 a.m. to 5 p.m. The…
Clark Street Live
Clark Street Live is a new two-day street festival in Wrigleyville on Clark Street between Addison Street and Newport Avenue. Hours are Saturday, September 26,…
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…
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.
