A street artist
Photograph: Courtesy of StarEvents
Photograph: Courtesy of StarEvents

The best September 2026 events in Chicago

Summer is almost over, but September in Chicago is packed with things to do, including festivals, exhibits and concerts.

Shannon Shreibak
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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 music 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 Hyde Park Jazz Festival, Printers Row Lit Fest and Taste of Chicago. 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 2026

The best events in Chicago this September

  • Shopping
  • Markets and fairs
  • West Loop
  • price 1 of 4
  • Recommended
Get ready to hunt for some new (and old) treasures! The beloved Randolph Street Market Festival is back with two days of curated, European-style vintage and antique shopping. Browse wares from hundreds of vendors, or grab a cocktail and bite to eat from local restaurants while tapping your toes to live music. 
  • Things to do
  • Fireworks
  • Streeterville
  • Recommended
During the summer, the Chicago attraction hosts twice-weekly fireworks shows (on Wednesdays at 9pm and Saturdays at 10pm) from Memorial Day weekend through Labor Day weekend, with stunning views available from across the pier's public spaces. During the winter months, the pyrotechnics return for a much-needed encore. If you're feeling weary of crowds, you can also take in the show from nearby beaches or while cruising along the Lakefront Trail.
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  • Comedy
  • Uptown
  • Recommended
This weekly “live magazine” is a cavalcade of culture, politics and wit featuring journalists, actors, comedians and musicians offering idiosyncratic reports on the news of the day. Head to Uptown’s iconic Green Mill for drinks, hot takes and laughs; the longstanding Saturday afternoon edition tends to run about two and a half hours.
  • Things to do
  • Streeterville
Enjoy outdoor live music all summer long at the Navy Pier Beer Garden. The free series will feature local, regional and national acts performing countless genres and musical styles every weekend. Check the official Navy Pier website for the full lineup and schedule.
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  • Sports and fitness
  • Millennium Park
Spin classes and weight lifting can wait for the winter. This summer, jump start your weekend with free cardio kickboxing, yoga, pilates and Zumba classes on Millennium Park’s Great Lawn and in Wrigley Square every Saturday from May through August.
  • Music
  • Jazz
  • Museum Campus
  • price 2 of 4
  • Recommended
The Shedd Aquarium's weekly summer concert series presents a rotating lineup of jazz bands on its scenic lakeside terrace, where attendees can dance, have a drink and get a great view of the Navy Pier fireworks. Guests also get access to the Shedd's exhibitions, meaning that you can gaze at the creatures that inhabit the Caribbean Reef, snap a picture of a cute sea otter or touch a sea star.
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  • Things to do
  • Exhibitions
  • Avondale
With soundstage-sized pieces like horned sculptures emitting soap bubbles, inflated spheres bedecked in abstract squiggles and surreal faceless figures hovering in space, “EmotionAir” reimagines the humble balloon as any other artistic medium—a conduit for creativity and emotion. 
  • Things to do
  • Exhibitions
  • Museum Campus
Whether you’re parenting a pint-sized Pokémon devotee or a nostalgic millennial still clinging to a holographic Charizard card for its “possible resale value” (guilty), the Pokémon Fossil Museum is designed to surprise and delight. Making its U.S. debut at the Field Museum in spring 2026, the international exhibition invites visitors to compare Fossil Pokémon like Tyrantrum and Archeops with real-world fossils—including SUE the T. rex. Expect Pokémon models, real fossil excavation tools and immersive soundscapes throughout.
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  • Museums
  • Museum Campus
Escape the planet with exhibits about the first lunar missions, the solar system and more, plus immersive shows in the dome theater. Stationed just a stone's throw away from the Adler, the Doane Observatory is also home to the largest public telescope in the area and gathers 7,000 times more light than the human eye. Every Wednesday, the Adler stays open late from 4pm-10pm so that folks can visit after work or school. And best of all, admission is free on those nights for Illinois residents.
  • Music
  • Latin and world
  • Loop
Explore music from around the globe during this annual festival, now in its 24th year, which brings a wide array of performers to venues across the city for free musical performances. Experience sounds and subgenres from regions like Brazil, South Korea, Senegal and more. For a full list of performances, visit the festival's website. 

GYG Chicago TTD

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