Everything Fun You Can Do in Chicago This Weekend

These are all your local must-hit music and food festivals, events, movies, markets, deals, and concerts to help you make the most of your weekend.

 amdurproductions
Fall Lincoln Roscoe Art & Craft Fair | amdurproductions
Fall Lincoln Roscoe Art & Craft Fair | amdurproductions

The full glory of fall in Chicago will be on full display as September turns into October and the city turns up the volume on its seasonal activities with a pumpkin spiced-assortment of events from arts and music festivals to a block party outside Empty Bottle and a chicken wing fest outside a church. Here’s everything fun you can do in Chicago this weekend.

Friday, September 30 - Sunday, October 2
Various Andersonville locations
More than 40 Andersonville businesses welcome 100+ artists to turn coffee shops, bookstores, shops, and yes—even a funeral home—into pop-up galleries for the weekend along with parties and an equity and inclusion initiative with the Hyde Park Chamber of Commerce called “100 Years, 100 Blocks.”
Cost: Free

Friday, September 30 - Sunday, October 30
Lincoln Park Zoo
Lincoln Park Zoo’s annual celebration of all things fall is a family-friendly feast for the senses with a pumpkin patch, Ferris wheel, harvest maze, live music, drag storytime, live pumpkin carving, and—you know—animals and stuff.
Cost: Free

Friday, September 30 - Sunday, October 9
Various locations
Music venues across the city including Schubas, Reggies, and Sleeping Village host world music acts in addition to a Global Peace Picnic at the Humboldt Park Boathouse and the largest all-night celebration of Indian classical music in the US at Chicago Cultural Center.
Cost: Free

Friday, September 30
Dank Haus
The Cystic Fibrosis Foundation’s annual fundraiser showcases high-end beers from 20+ local craft breweries along with Oktoberfest-styled eats and music in a German beer hall.
Cost: $75+

Saturday, October 1
Empty Bottle
Empty Bottle’s second annual edition of this neighborhood-centric block party celebrates Western Avenue in all its eminence with live music (duh), pop-up vendors, a dunk tank, photo booth, and kids activities alongside eats from Pizza Friendly Pizza and more.
Cost: Free

Saturday, October 1
NOW Arena
It wouldn’t be fall without some sort of weird Celtic festival and this event more than fits the bill with a Celtic marketplace, live music, Celtic food, Irish dancers, clans from various Celtic lands and “meet and greets with birds of prey.” Careful on that last one.
Cost: Free

Saturday, October 1 - Sunday, October 2
St. Michael Church parking lot
Did someone say outdoor chicken wing party? Yes, someone did say outdoor chicken wing party. And that someone is us. Did someone say outdoor chicken wing party in a church parking lot? Also us. You know what to do.
Cost: $14 - $79

Saturday, October 1 - Sunday, October 2
Lincoln Avenue from Roscoe to School
Neighborhood outdoor art fests aren’t just for summer, as this fall-themed event so clearly demonstrates with the aid of 60+ juried art exhibitors hawking unique wares including Chicago flag- and Wrigley Field-inspired items.
Cost: Free

Sunday, October 2
Sleeping Village
One of Chicago’s coolest bars gets into the Oktoberfest game with this outdoor patio event featuring exclusive tappings of German brews, German eats and DJs spinning “German polka bliss.” Let those last three words sink in for a moment.
Cost: Free

Sunday, October 2
Soldier Field
Enjoy the great outdoors while raising money to help fight AIDS at this annual charity run/walk featuring 5K and 10K courses plus opening and closing ceremonies and a MolsonCoors beer garden to hit up once you’re done.
Cost: $25+

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Jay Gentile is an award-winning freelance journalist specializing in travel, food & drink, culture, events and entertainment stories. In addition to Thrillist, you can find his work in The Washington Post, The Guardian, CNN Travel, Chicago Tribune, Lonely Planet, VICE, Outside Magazine and more. Follow @thejaygentile.