CHICAGO – Hello fall! It’s the first official weekend of the season, and Chicago knows how to celebrate. From Oktoberfest celebrations, pop-ups and street festivals to concerts and sporting events, here’s a list of things to do in Sept. 26-28.
What concerts are in Chicago this weekend?
Sept. 26: Cartel at House of Blues Chicago
Sept. 26: Turnstile at Huntington Bank Pavilion at Northerly Island
Sept. 26: Wolf Alice at Vic Theater
Sept. 27: Lil Tracy at House of Blues Chicago
Sept. 27: Papa Roach at Credit Union 1 Amphitheatre
Sept. 27: Mountain Goats at The Salt Shed Indoors
Sept. 27: Morrissey at Byline Bank Aragon Ballroom
Sept. 27: Bruce Dickinson at Riviera Theatre
Sept. 28: Corinne Bailey Rae at Cahn Auditorium Evanston
Sept. 28: Joss Stone at North Shore Center Skokie
Sept. 28: The California Honeydrops at Thalia Hall
Sept. 28: Sleep Token at Allstate Arena
Multiple dates: Maná at United Center
What sporting events are in Chicago this weekend?
Sept. 27: Chicago Fire FC versus Columbus Crew
Multiple dates: Chicago Cubs versus St. Louis Cardinals
What theatre and comedy shows are in the Chicago area this weekend?
Brent Morin at Chicago Improv
The Twenty-Sided Tavern
TWIHARD! A Twilight Musical Parody
The World of Hans Zimmer at Allstate Arena
Dial M for Murder
Louis CK at The Chicago Theatre
RuPaul’s Drag Race Werq The World Tour at Rosemont Theatre
What festivals are in Chicago this weekend?
Chicago Gourmet Festival
Chicago Gourmet returns Sept. 25-28 on the Harris Theater Rooftop at Millennium Park, showcasing top chefs, tastings and specialty food events across the city. The upscale culinary festival includes everything from wine pairings to the fan-favorite Burger Battle.
All you can Eataly SeptemberFest
On Sept. 26, Eataly Chicago will host an all-access, one-night-only food and drink extravaganza featuring 40+ Italian bites, 30+ pours, live music, and comedy from The Second City. Tickets start at $110 for the 21+ event, which runs 7-11p.m. throughout the marketplace.
Hyde Park Jazz Festival
The Hyde Park Jazz Festival takes over Chicago’s South Side Sept. 27-28 with two days of live music at outdoor stages and historic venues. The free event features world-class jazz, local talent and a community-driven atmosphere.
Filipino Cultural Festival
Celebrate Filipino heritage at the Musika SamaSama Festival on Sept. 27 from noon to 4 p.m. at Eugene Field Park. The free event includes traditional food, crafts and live performances from local musicians.
Hubbard Haus Oktoberfest
River North debuts the Hubbard Haus Oktoberfest on Sept. 27, transforming Hubbard Street into a full Bavarian-style street fest with beer halls, live bands, DJs and German-inspired eats. All-access passes start at $15, with proceeds supporting local businesses.
Lincoln Park Zoo Fall Fest
Lincoln Park Zoo’s free Fall Fest kicks off Sept. 26 with pumpkin patches, season treats, and fall-themed animal enrichment. Families can also enjoy rides, games and a pumpkin pop-up bar on weekends through Oct. 26.
St. Alphonsus Oktoberfest
The 23rd annual St. Alphonsus Oktoberfest returns Sept. 26-28 with Bavarian cuisine, beer, and live music at 1429 W. Wellington Ave. The weekend includes two stages of entertainment and a Sunday Kinderfest for families.
Brookfield Zoo Hispanic Heritage Fest
Brookfield Zoo launches its first Hispanic Heritage Fest on Sept. 27 with cultural performances, storytimes, and Latin music across the zoo. The event is included with admission and features family-friendly activities throughout the day.
Randolph Street Market Festival
The Randolph Street Market returns Sept. 27-28 with 200+ vendors selling vintage goods, antiques and indie fashion in the West Loop. Tickets start at $12 online, with live music, food and cocktails included in the weekend experience.
What events are in Chicago this weekend?
St. Helen Carnival
The St. Helen Carnival runs Sept. 25-28 in Ukrainian Village with rides, games, music and food. Proceeds from the entry event benefit St. Helen School programs.
Goose Island 312 Block Party
The 312 Block Party is back Sept. 27 outside Goose Island Taproom. Attendees can expect more than 50 beer selections and live performances from American Football and Hinds. The festival runs 3-10 p.m. and is free to attend for ages 21+.
Jack’s Pumpkin Pop-Up
Jack’s Pumpkin Pop-Up is back through Nov. 2 with Chicago’s largest corn maze, carnival games, axe throwing, and more than 10,000 pumpkins. The seasonal attraction offers photo ops, bars and fall fun for all ages.
TEDxChicago: The Future is Human
TEDxChicago 2025 takes place Sept. 27, bringing together speakers, performers and artists to explore ideas of connection, justice and sustainability. Tickets can be purchased online.
Navy Pier Open Air
Dance music legend Carl Cox closes out the Navy Pier Open Air season with an unforgettable lakefront show. The Ibiza icon brings explosive energy and signature sound to Chicago alongside John Digweed, Archie Hamilton b2b Sidney Charles and Muffy.
Driehaus Fall Market
The Driehaus Museum hosts its fall market Sept. 27 from 11 a.m. – 5 p.m. at the Murphy Auditorium with vintage jewelry, local crafts and artisan goods. Guests can also explore the new “Tiffany Lamos” exhibition inside the mansion.
Driehaus Museum opens ‘Tiffany Lamps: Beyond the Shade’ exhibition | ChicagoNOW
Earlier this month, the Driehaus Museum opened Tiffany Lamps: Beyond the Shade, an exhibition illuminating the volume and breadth of Louis C. Tiffany’s vast artistic production. From the 1890s through the 1920s, Tiffany Studios created a captivating range of decorative lighting fixtures that embraced the technological shift from oil lamps to electricity. The exhibition will explore the broader context of the iconic lamps—from materials, to design considerations, and the business of Tiffany Studios—to uncover their enduring popularity today.
Meet Me on Milwaukee
On Sept. 28, Milwaukee Avenue closes to cars between Damen and Ashland for a day of music, outdoor dining and activities. The pedestrian-only event runs 10 a.m. – 5 p.m and is free to the public.
