Chicago September 2022

Chicago September 2022 Events

Chicago September 2022 Events

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.

Broadway shows in Chicago in September

September Event Calendar

Bristol Renaissance Faire

Bristol Renaissance Faire

The Bristol Renaissance Faire, which starts in early/mid-July and continues through September, is an annual experience worth checking out. On Saturdays, Sundays, and Labor Day, you can attend an event that will make you feel like you just stepped out of a time machine! It will feature knights jousting, artisan markets, costumed-minstrels, games, shows, and more! Single-day passes for adults are $30 and $15 for kids 5-12; children under 5 get in for free! 

Taste of Polonia

Taste of Polonia

Head down to Jefferson Park to experience authentic Polish cultures and traditions at the Taste of Polonia. The 4-day annual Labor Day Weekend event will feature live music, food (such as polska kielbasa, potato pancakes, pierogi), adult beverages, tastings and cooking classes, exhibits, vendors, carnival rides, and more.

ARC Music Festival

ARC Music Festival Play Video

Chicago is known pretty well for being a city pioneer of house music. With that said, you should plan to put this house/electronic music festival on your to-do list for Labor Day weekend. ARC Fest is the perfect place for party goers that are eager to dance and rave, so head down to. Union Park for an unforgettable time. Click here for more info. 

Fifth Third Bike the Drive

Fifth Third Bike the Drive Play Video

The Fifth Third Bank Bike the Drive is a fundraiser for Active Trans, a nonprofit that strives to improve commuting for walkers, bikers, and public transportation users in Chicago. The 30-mile bike ride route will feature skyline and lake views throughout the city. Bikers of all skill levels can participate for as much as the route they choose to. Bike rentals will be available. Additional information on the 2022 ride will be available online soon. 

Riot Fest

Riot Fest Play Video

Get ready to RIOT at this 3-day annual festival that has a stacked lineup. This year's headliners include the Original Misfits, My Chemical Romance, and many more. Music festivals are back, and this is certainly one you won't want to miss.

Lakeview Taco Fest

Lakeview Taco Fest Play Video

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 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.

African Festival of the Arts

African Festival of the Arts Play Video

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 textile, and more. Presale festival tickets can be purchased online. Family and weekend passes are also available.

Roscoe Village Burger Fest

Roscoe Village Burger Fest Play Video

At the annual Roscoe Village Burger Festival, over a dozen eateries will come together to deliver some of the best burgers you’ll ever have! In addition to delicious beef burgers, turkey burgers, and veggie burgers, the festival will also feature BBQ, two stages with live music entertainment, a kids’ activity area, arts & craft vendors, and the opportunity for visitors to vote for the best Chicago burger.

Pitchfork Music Festival

Pitchfork Music Festival Play Video

Pitchfork has assembled a varied lineup for their annual festival. EDM, hip hop, rock, indie, and funk are all represented at the Pitchfork Music Festival.

Passport Vibes Afrobeat Street Fest

Passport Vibes Afrobeat Street Fest Play Video

This Passport Vibes fest is returning as one of the most diverse party experiences in Chicago. You'll feel like you're on an island vacation while being right in Chicago. Dance to music from international DJs that you can expect to be a mix of genres, including hip-hop, R&B, reggae, afrobeats and many more. There will also be food, crafts, and fun activities for entertainment. 

See what's happening in Chicago Today
Chicago Today

Chicago Events in September


Theater & Headliners



Upcoming events

Fri, Sep 30 at Subterranean The Social Experience: 90's & 2000's R&B Edition
Fri, Sep 30 at Subterranean THE CENTRAL, Cadence Fox, Lower Automation
Fri, Sep 30 at Subterranean Smith & Thell, Social Animals (solo)
Fri, Sep 30 at Subterranean Draggy Tingz: Hosted by Logan Zass
Fri, Sep 30 at Beauty Bar The Grind
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.