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

  • Movies
  • Recommended
From June through September, more than 90 movies will screen in parks across Chicago as part of the Park District's annual Movies in the Parks program. From recent blockbusters like Zootopia 2 and Freakier Friday to classics like Back to the Future and Jumangi, you're sure to find something good to watch (for free!) beneath the stars this summer. Screenings typically begin at 8:45pm, or dusk, each evening. Take a look at the full list of movies and participating parks.
  • 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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  • Things to do
  • Streeterville
  • price 1 of 4
  • Recommended
Navy Pier's former Crystal Gardens space transforms into a retro roller skating rink this summer. Grab your skates (or borrow a pair; they're included with your ticket) and hit the rink for old-school fun, plus an arcade, photo booth, drinks and groovy disco tunes. At night, the Skate After Dark party turns up the energy for the 21+ crowd with DJ sets on select nights throughout the summer.
  • 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.
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  • 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.
  • 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.
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  • Comedy
  • Stand-up
  • Recommended
Located inside The Den, a 1920s greystone-turned-hotel in Lakeview, the Blind Wolf Speakeasy is an intimate, approachable bar, event venue and home to a free weekly comedy show. Blind Wolf Comedy hosts a rotating roster of Chicago comics each Wednesday at 8pm, as well as open mic nights on Thursdays at 7:30pm. There's no cost to attend, but you can reserve a seat through their Instagram page.
  • Things to do
  • Suburbs
The oldest music festival in North America plays host to more than 90 shows throughout summer, featuring big-name headliners like Paul Simon, Alabama Shakes and Chance the Rapper. Check out the full schedule of artists coming to Highland Park this year, and don't forget to pack a picnic.
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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. 
  • Shopping
  • Markets and fairs
  • Little Italy, UIC
Originally established in the late 1800s, the Maxwell Street Market brought vendors, musicians and cooks to an open-air flea market where shoppers could find just about anything they wanted. The market introduced the Maxwell Street Polish sausage, provided a venue for rising Chicago blues musicians and was immortalized in a scene in The Blues Brothers. These days, the market sets up on Maxwell Street, between South Halsted Street and South Union Avenue on Sundays, where visitors will find vendors hawking their wares, an abundance of delicious Mexican food and occasional performances by local bands and dance troupes. 

GYG Chicago TTD

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