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Photograph: Anne Evans | Bike the Drive
Photograph: Anne Evans

The best September 2027 events in Chicago

Summer is almost over, but there are still plenty of fun things to do in Chicago this month.

Lauren Brocato
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September might be here, but don't despair—there are still plenty of things to do in Chicago—whether you're still embracing a summertime state of mind or welcoming fall with open arms. From Oktoberfest celebrations to outdoor festivals (including Riot Fest), we've still got plenty of warm weather fun to take advantage of before the leaves start to turn and the temperature drops. Soak up the sun at the best Chicago beaches and rooftop bars, or spend your weekends checking out the end of festival season at events like the Chicago Jazz Fest and the World Music Festival. And if you really can't wait for fall to arrive, might we suggest some early leaf peeping and apple picking? Whatever your mood, you'll find plenty of ways to keep busy with our roundup of the best things to do in Chicago this September. 

RECOMMENDED: Events calendar for Chicago in 2027

The best events in Chicago this September

  • Things to do
  • Late openings
  • Wicker Park
  • Recommended
Check out galleries and artistic spaces around Wicker Park and Bucktown during this free monthly event on the first Friday of each month. Venues will keep their doors open until 8pm so guests can meet gallery owners and artists, and explore a range of local art. Participating spots include Graveface Chicago, Little Broken Things, Heaven Gallery, David Leonardis Gallery and more.

GYG Chicago TTD

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