10 Things That Should Be On Illinoisans' Calendar This September

ILLINOIS — September is always a busy month as Illinoisans return to school and work routines, and 2025 is no exception.

If it’s not a meeting with your kids’ teachers, it’s a football game or fall musical. If it’s not an imposing deadline at work, out-of-town business trips and demands on your volunteer time.

Don’t forget to schedule date night, family day or even “you” time before the usually mild month of September slips away. To help you fill out your calendar, we’ve rounded up 10 can’t-miss events from around the Chicagoland area.

Chicago Jazz Festival

• When: Aug. 28-31
• What: Programmed by the Jazz Institute of Chicago, the Labor Day weekend tradition highlights all forms of jazz through free programming that showcases national and international artists.
• Where: Chicago Cultural Center and Millennium Park, adjacent to one another off Michigan Avenue
• Admission: Free

Taste of Chicago

• When: Sept. 5-7
• What: The 45th annual Taste of Chicago will bring dozens of food vendors from across the city together for the weekend. Live performances, community dance lessons, family-friendly activities, pop-ups and more are planned.
• Where: Grant Park
• Admission: Free

Chicago German-American Oktoberfest

• When: Sept. 5-7
• What: Commemorate fall with the German-inspired event featuring beer, pretzels, German delicacies, a parade, live performances and carnival games for kids.
• Where: 4521 Lincoln Ave., Chicago
• Admission: Free

Kane County Flea Market

• When: Sept. 6-7
• What: Up to 400 vendors gather to sell everything from refurnished furniture, antiques, sports collectibles and more.
• Where: 525 S. Randall Road, St. Charles
• Admission: $6 (Children under 12 are free when accompanied by an adult)

Highland Park Vintage Shindig

• When: Sept. 13-14
• What: A three-in-one event, both indoors and outdoors, where vintage lovers can hunt for vintage and antique goods and records at about 75 vendors.
• Where: Highland Park Community House, 1991 Sheridan Road; and The Art Center Highland Park, 1957 Sheridan Road
• Admission: $10 online or $12 at the door

Riot Fest

• When: Sept. 19-21
• What: Blink-182, Weezer, Jack White, Green Day and dozens of other artists will perform at this three-day punk rock music festival, considered one of the largest independently owned music festivals in the country.
• Where: Douglas Park
• Admission: Starting at $125

Tacos and Tequila Festival

• When: Sept. 20
• What: A throwback hip-hop-style festival, the event will feature performances from hip-hop artists, craft margaritas, a tequila-tasting lounge, locally crafted tacos and more.
• Where: Northwestern Medicine Field in Geneva
• Admission: Starting at $89

Long Grove Apple Fest

• When: Sept. 26-28
• What: A weekend about everything apple, the Long Grove Apple Festival serves apples every way you can think of, while musicians perform and everyone in the family enjoys a carnival.
• Where: Downtown Long Grove
• Admission: Starting at $7

Revelry Food and Wine Festival

• When: Sept. 4-7
• What: A four-day food and wine festival showcasing celebrity chefs, beverage professionals and musicians. Ferraris, wagyu burgers and an open-air dinner are just two highlights of the festival. Revelry Food and Wine donates a portion of its proceeds to the Northern Illinois Food Bank.
• Where: Multiple locations in Lake Forest and Libertyville
• Admission: Starting at $78

Hyde Park Jazz Festival

• When: Sept. 27-28
• What: The 19th annual event will feature more than 30 jazz musicians at venues across the South Side neighborhood.
• Where: Nine venues in Hyde Park
• Admission: Free

Are you planning an event this fall? Feature it, so nearby readers see it all across Patch — including in roundups like this!