Five Things To Do in Chicago: October 3–5, 2025

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

Celebrate Local Creativity at Andersonville Arts Weekend.

More than 30 local businesses transform into pop-up galleries during Andersonville Arts Weekend, showcasing work from Chicago artists across mediums. Opening receptions kick things off Friday, followed by a weekend of browsing, mingling, and celebrating the neighborhood's creative spirit. This year's edition also honors Todd Mack, artist and founder of Foursided, whose vision helped shape Andersonville's arts community.

Date: Oct. 3–5
Time: Various Times
Cost: Free
Location: Various Locations
More Info: andersonville.org

  
Sip and Stroll at Lincoln Park Wine Fest.

Jonquil Park becomes an open-air tasting room for Lincoln Park Wine Fest, where dozens of varietals are poured alongside food and live entertainment. The festival is part of the Chicago Wine Fest series and offers the chance to sip reds, whites, and rosés while enjoying crisp fall weather in one of the city's most charming neighborhoods.

Date: Oct. 3–5
Time: Fri. 5–10 p.m., Sat. 11 a.m.–10 p.m., Sun. 11 a.m.–7 p.m.
Cost: $30+
Location: Jonquil Park, 1001 W. Wrightwood Ave.
More Info:chicagoevents.com

Have Bavarian Fun at Oktoberfest on Division Street.

Division Street turns into a Bavarian-style block party for Oktoberfest on Division, hosted by neighborhood staples like The Lodge Tavern, She-nannigans, and Butch McGuire's. Expect overflowing steins, live music, and contests from stein-holding to German musical chairs.

Date: Oct. 3–4
Time: Fri. 3–10 p.m., Sat 12–10 p.m.
Cost: $12+
Location: The Lodge Tavern, 21 W. Division St.
More Info:exploretock.com 

See Chinatown Glow at Moon Festival.

Chicago's Chinatown lights up for the Moon Festival, a Mid-Autumn tradition marked by glowing lanterns, cultural performances, and—of course—mooncakes. Guests can explore food and art booths, enjoy live entertainment, and take in the giant illuminated moon installation that anchors the celebration.

Date: Oct. 4
Time: 2–9 p.m.
Cost: Free
Location: Chinatown Square, 2130 S. Archer Ave.
More Info: gooseisland.com 

Spark Curiosity at STEAM-Powered Saturday

The Chicago Public Library's STEAM-Powered Saturday brings hands-on fun for curious kids and families. Activities range from glow-in-the-dark slime and LEGO engineering to live animal encounters and swamp science. Partner organizations including the Art Institute, Museum of Science and Industry, and Shedd Aquarium join in for a day of discovery.

Date: Oct. 4
Time: 11 a.m.–3 p.m.
Cost: Free
Location: Harold Washington Library, 400 S. State St.
More Info:chipublib.bibliocommons.com