Chicago September 2025

Chicago September 2025 Events

Chicago September 2025 Events

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Spend Labor Day Weekend in Chicago This Year

Average temperature low and high: 62°- 74°
September marks the end of the Windy City's busy summer tourism season, but that doesn't mean that events in Chicago slow down. Consider celebrating Labor Day Weekend here, as there will be lots of things to do, like the annual Taste of Polonia event or Expo Chicago. The weather tends to be enjoyed throughout the month as it's the perfect median between the hot summer and the upcoming chillier months.
Chicago September Festivities Calendar
Things to do in Chicago September
Chicago Nightclub Events in September
Chicago Sporting Events, Concerts & Show Tickets in September

Broadway shows in Chicago in September

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September Event Calendar

WingOut Chicago

Date to be confirmed Gallagher Way View on Map
WingOut Chicago

Whether you prefer drums or flats, the annual WingOut Chicago event will feature some of the best chicken wings the city has to offer. Over 20 varieties will be served (classic buffalo, honey chili, jerk, wood smoked, spicy garlic, southern BBQ, habanero hot, & more.) Some of this year’s vendors include Jake Melnick’s, Woodie’s Flat, Smoke Daddy BBQ, Harold’s Chicken, Joker’s Cajun Smokehouse and more. Attendees will have the chance to enjoy live music, vote for Chicago’s top wings and have access to all-you-can-eat wings. Additional food vendors with a variety of entrees and options will also be available - Tickets options include go VIP, go pre-sale & save, and go day of.

Chicago Jazz Festival

Date to be confirmed Millineum Park/ Chicago Cultural Center View on Map
Chicago Jazz Festival
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What more can you ask for than a free jazz concert with a fantastic lineup located in an aesthetically pleasing, historic park? Head down the Millennium Park to experience the 45th-annual Chicago Jazz Festival. The Labor Day tradition will also feature free, live jazz performances at other venues across the city; the best local and international jazz artists will be showcased. This special event is put on by the Department of Cultural Affairs and Special Events and programmed by the Jazz Institute of Chicago.

Taste of Polonia

Date to be confirmed West Lawrence Avenue View on Map
Taste of Polonia

Head down to Copernicus Center to experience authentic Polish culture and traditions at the Taste of Polonia festival. The 4-day annual Labor Day Weekend event will feature live music and authentic Polish food such as polska kielbasa, potato pancakes and, of course, pierogi. A colorful selection of adult beverages, including craft beers, combined with food tastings and cooking classes, exhibits, vendors, carnival rides, and much more, make this a fantastic time for the entire family. There will be music and theater performances all weekend too. Single-day passes start at $10, and $45 gets you a 4-day pass. Children under 12 enter free.

ARC Music Festival

Date to be confirmed Union Park View on Map

The ARC music festival is a dance and music extravaganza, and this year's lineup includes Anotr, Pawsa, DJ Lady D and dozens more of the music scene's best electronic and house music artists. You might just find your next favorite DJ here. 3 days, multiple stages, and a stellar lineup - it's all coming to Chicago's Union Park this August. Passes for the entire festival start at $389, and single-day tickets are also available. Look out for ARC After Dark events where the party continues. This event is for 21 and over, and festival goers are advised to use public transport to reach the venue.

Bike the Drive

Date to be confirmed Grant Park Butler Field View on Map
Bike the Drive
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Over 20,000 riders attended last year's Bike the Drive. The event is a fundraiser for Active Trans, a nonprofit that strives to improve commuting for Chicago walkers, bikers, and public transportation users. The 30-mile bike ride route will feature skyline and lake views throughout the city, and bikers of all skill levels can participate for as much as the route they choose. The ride starts from Butler Field in Grant Park, but riders can join in from Bryn Mawr Avenue, Fullerton Avenue, Oakwood Boulevard, and the Museum of Science & Industry. The ride starts at 6.30 A.M. and lasts till 10.30 A.M., after which riders can join in the festival at Butler Field. Register as a member for $63. The regular price for general admission is $73. Youngsters will have to pay only $18 to register.

Lakeview Taco Fest

Date to be confirmed Southport between Addison and Roscoe View on Map
Lakeview Taco Fest
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Tacos, anyone? From traditional chicken, steak, chorizo, and beef tacos to more unique mushrooms, seafood, goat, and duck tacos, get the chance to try some from over a dozen restaurants across the area, then decide who has the best at the Lakeview Taco Fest. The festival, returning for its tenth year, will also feature beer, live music on two stages, a kids’ area, and Mexican wrestlers. A $10 donation is suggested for admittance; proceeds benefit the Friends of Lakeview.

2024 UNCF Walk for Education – Chicago

Date to be confirmed South Lake Shore at 39th Street View on Map
2024 UNCF Walk for Education – Chicago
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Education is the key to success. Thus, the United Negro Collge Fund has followed a strict mission for decades, offering resources for students, scholarships and other forms of financial assistance for those in underserved Black communities. Join in and add your support during the 2024 UNCF Walk this September 7. The gathering also includes appearances by some of the city's most notable thought leaders and live entertainment.

Riot Fest

Date to be confirmed Douglass Park View on Map
Riot Fest
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Get ready to Riot at this 3-day annual festival that has a stacked lineup. This year's headliners include Fall Out Boy, Beck Pavement, Lamb of God, Oliver Tree, Spoon, St. Vincent, Public Enemy, Sum 41, New Found Glory, Dr. Dog and many more. Music festivals are back, and this is certainly one you won't want to miss.

African Festival of the Arts

Aug 30 - Sep 2, 2025 Washington Park View on Map
African Festival of the Arts
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Spend part of your Labor Day weekend in Chicago celebrating African art, crafts, music, food, and entertainment. The annual African Festival of the Arts will take place in a simulated African village for a unique cultural experience. There will be interactive engagements, drumming circles, museum-quality artifacts, colorful handwoven fabric and textiles. Presale festival tickets can be purchased online at $30 per adult and $10 per child under 13. Family and weekend passes are also available.

Chicago Events in September

Concerts

Theater & Headliners

Sports

Nightclubs

Nightclubs in Miami
Best Nightclubs in Chicago 2024
Things to do in Chicago

Things to Do in Chicago in September

See a Movie in a Park

See a Movie in a Park
For the 21st year, Chicago will be screening movies in outdoor parks during evenings around the city. It's the perfect way to social distance while still having an enjoyable, free, and memorable evening. All movies begin at dusk. Download the MyChi Parks app for movie lineups and locations.

Grab a Slice of Deep Dish Pizza

Grab a Slice of Deep Dish Pizza
Many people travel to Chicago just for the food, and rightfully so,  but you can't leave without having one of Chicago's most popular and beloved foods: deep dish pizza. Head over to Lou Malnati’s, a popular pizza spot in the Windy City. As lines are usually lengthy at this particular spot, it's suggested to go either for early lunch or for a late night stop.
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