Eight Things To Do in the City and Western Suburbs: September 26 to September 28

From orchard visits to neighborhood fests, fall is full of excuses to get outside and soak it all in. We've rounded up a few local happenings to add to your list this weekend.

Spend Your Evening at Uncorked.

Sip wine under the stars at the Oak Park Conservatory's Rubinstein Garden. Your ticket includes two drinks, appetizers, and a guided tour of the showrooms, making this evening more than just a night out. With music filling the air and friends gathered in a lush setting, Uncorked offers a relaxed sendoff to summer.

Date: Sept. 26
Time: 6–8 p.m.
Cost: $25
Location: Oak Park Conservatory, 615 Garfield St., Oak Park
More Info: pdop.org  

Get Cozy at Flannel Fest.

Pull on your favorite plaid for a night of country tunes, barbecue, and cold beer. The Whiskey Road Band headlines the evening, with line dancing, a mechanical bull, and the Flannel Face-Off adding to the fun. From food to competition, Flannel Fest serves up fall with a side of country flair.

Date: Sept. 26
Time: 6–8:30 p.m.
Cost: Free
Location: Fishel Park, 1036 Grove St., Downers Grove
More Info: dgparks.org

Raise a Stein at Immanuel Lutheran's Oktoberfest.

This annual celebration combines German food, live music, and family-friendly activities. Polka band Die Musikmeisters set the tone while guests enjoy bratwurst, schnitzel, strudel and more. Kids can join games and activities in the supervised zone, while adults stick around for raffles, dancing, and a night of community.

Date: Sept. 27
Time: 3–8 p.m.
Cost: Kids $20; Adults $25
Location: Immanuel Lutheran Church & School, 148 E. 3rd St., Elmhurst
More Info: ilselmhurst.org 

Indulge at Chicago Gourmet.

The city's premier food festival returns with a full lineup of star chefs, themed tastings, and rooftop views. Highlights include Tacos & Tequila hosted by Rick Bayless, the fan-favorite Hamburger Hop, and Saturday's Grand Cru, featuring top-tier cuisine paired with fine wine and spirits. The weekend closes with Rise & Shine Gourmet, a lively brunch capped with cocktails and music. From burgers to brunch, Chicago Gourmet serves up a feast for every appetite.

Date: Sept. 26-28
Time: Various Times
Cost: $85+
Location: Various Locations
More Info: chicagogourmet.org  

Celebrate Tradition at Czech Heritage Week.

Chicago's Czech community closes out its weeklong celebration with concerts, films, and family-friendly events across the city. The program highlights the long-standing cultural ties between Chicago and Prague, including a special concert honoring their sister city relationship. With deep roots in the city, Czech Heritage Week offers a glimpse into a culture that continues to shape Chicago's story.

Date: Sept. 26-28
Time: Various Times
Cost: Various Pricing
Location: Various Locations
More Info: mzv.gov.cz

Experience Musika SamaSama Filipino Festival.

Chicago's only Filipino cultural festival brings music, food, and community to Field Park. The SamaSama Project headlines an evening filled with live performances, storytelling, and family activities. Guests can sample Filipino dishes, shop artisan crafts, and enjoy bounce houses and hands-on fun for kids. Free and open to all, Musika SamaSama is an important celebration of heritage.

Date: Sept. 27
Time: 12–4 p.m.
Cost: Free
Location: Field Park, 5100 N. Ridgeway Ave.
More Info: eventbrite.com

Head to the 312 Block Party.

Goose Island's 312 Block Party fills the West Loop with music, food trucks, and more than 50 beers on tap. Along with specialty tappings and neighborhood brewery pours, this street fest features national and local acts on stage. Equal parts block party and beer festival, it's a Chicago tradition with plenty to sample and plenty to hear.

Date: Sept. 27
Time: 3–10 p.m.
Cost: Free
Location: Goose Island Brewery, 1800 W. Fulton St.
More Info: gooseisland.com

Fun for All at St. Helen Carnival.

Now in its 19th year, St. Helen Carnival takes over Ukrainian Village with rides, food, and live music. The weekend lineup spans yacht rock, indie pop, Grateful Dead tributes, and Latin dance rhythms. Carnival games and kid-friendly activities run alongside beer tents and local fare, making this fundraiser a community favorite. Proceeds support St. Helen School's educational programs.

Date: Sept. 26-28
Time: Fri.5–10 p.m., Sat. 12–10 p.m.,  Sun. 12–8 p.m.
Cost: Free
Location: St. Helen School, 2347 W. Augusta Blvd.
More Info: sthelenchicago.org