Hey Chicago!
We hope you’ve enjoyed the many events and festivals hosted around the city this summer. Although summer is coming to an end, we’ll close out August with the Air and Water Show and the Chicago House Music Festival and Conference.Â
And that doesn’t mean that the fun is over, because September has a ton of stuff lined up for Chicago. Labor Day weekend alone throws four festivals at you at the same time, and there’s plenty more for the rest of the month. So in this week’s article, we’re covering all the festivities you can enjoy (many without the kids).
So hey! We’re the Ben Lalez Team, a top-producing real estate team in Chicago who’s helped well over 1,000+ families move in and around the city. We’re always talking about real estate during the day, so this is our outlet to talk about everything else about Chicago. Every week, we try to cover lifestyle, history, events, resources, and fun facts about the city.
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Okay, here’s what September has in store. Let’s get into it!
Chicago Jazz Festival
September 3 – 6
The month kicks off with a Chicago classic. Of course, we’re talking about the Chicago Jazz Festival that runs Thursday, September 3rd through the 6th at Millennium Park, with free evening concerts at the Jay Pritzker Pavilion and daytime performances at the Chicago Cultural Center. You’ll enjoy a mix of national headliners and local legends. Best of all, it’s all free!
ARC Music Festival
September 4 – 7
If house and techno are your passion, the ARC Music Festival takes over Union Park from September 4th to the 7th. You’ll find Chicago’s roots in the genre, plus a global lineup of DJs across multiple stages. There’s also ARC After Dark, a run of late-night club shows around the city. It’s the perfect excuse to dance 4 days straight.
North Coast Music Festival
September 4 – 6
But wait, because on the same weekend, the North Coast Music Festival is happening at SeatGeek Stadium in Bridgeview for EDM fans as well. More than 75 artists across six stages, with a heavy EDM and bass music lineup, plus art installations and food stands. It’s a bit of a trip from the city, but shuttle and transit options are available.
Taste of Polonia
September 4 – 7
Taste of Polonia returns to the Copernicus Center in Jefferson Park for the full long weekend, September 4 – 7. It prides itself as the largest Polish festival in the country. We’re talking pierogis, kielbasa, pastries, Polish beer and vodka! There’ll be live music across multiple stages and rides and games for the kids.
Great American Lobster Fest
September 5 – 6
Navy Pier hosts the Great American Lobster Fest on Saturday and Sunday, September 5 and 6, right on the lakefront at 900 E. Grand Avenue. You can pre-order a whole lobster dinner or grab something else off the seafood menu, all with live music and a view of Lake Michigan. But why would you want something else? Get the lobster, trust us.
German-American Fest / Oktoberfest
September 11 – 13
The following weekend, Lincoln Square kicks off Oktoberfest season with the German-American Fest, Friday through Sunday, September 11th to 13th. It’s centered around Western and Lincoln, with beer and wine tents, sausages, pretzels, oompah bands, and folk dancing. The Von Steuben Parade steps off Saturday. For more family-friendly activities, visit during the day. Evenings are best if you’re looking for the beer garden.
El Grito Chicago
September 12 – 13
Grant Park hosts El Grito Chicago on September 12th and 13th, a major Mexican Independence Day festival that’s back after a bit of a hiatus. There’s live music, mariachi, a grito ceremony, fireworks, and food vendors serving tacos and all of your favorite Mexican dishes. This one is popular and draws people from all over the city and the suburbs, so plan to get there early.
Printers Row Lit Fest
September 12 – 13
Printers Row Lit Fest turns South Dearborn Street into an outdoor book fair on the weekend of September 12th and 13th. It’s the largest free outdoor literary festival in the Midwest, with publishers, bookstores, and indie presses showing up alongside author talks, panels, and signings.
79th Street Renaissance Festival
September 12
On the South Side, the 79th Street Renaissance Festival celebrates its 21st year on September 12. There’ll be local food vendors, retail booths, community organizations, youth activities, and a main stage running all day.
Englewood Music Festival
September 12
That same Saturday, the Englewood Music Festival will be running along Halsted around 63rd and 64th streets. It’ll feature local talent and neighborhood vendors, with a lineup that usually covers gospel, R&B, hip-hop, and soul. Pair it with the 79th Street Renaissance Festival, and you’ve got a full South Side day!
Riot Fest & Carnival
September 18 – 20
Riot Fest is back in Douglass Park with more than 90 punk, rock, and alternative acts across multiple stages. There’s a small carnival, plenty of art and merch, and a ton of food and drink vendors. It’s still one of the city’s biggest late-summer music festivals that you don’t want to miss.
Retro on Roscoe
September 18 – 20
Roscoe Village has its own event that weekend, with Retro on Roscoe. Multiple stages of throwback cover bands and classic rock, a vintage and antique car show, kids’ activities, and vendors and restaurant patios to enjoy while summer is still here.
Chicago Live!
September 19 – 20
Navy Pier hosts Chicago Live! for its sixth year on Saturday and Sunday, September 19 and 20. Stages across the pier will feature music, dance, theater, and comedy from the city’s major arts and cultural groups. This event is totally free, so make sure to get out there.
Lakeview East Festival of the Arts
September 19 – 20
Broadway in Lakeview East closes down that same weekend for the Lakeview East Festival of the Arts. There’ll be more than 150 artists, two music stages, live art demos, and plenty of food and drink. It’s one of the more curated art festivals in the city, so it’s worth checking out if you’re an art fan.
World Dumpling Fest
September 19 – 20
And on the same weekend, we’ve got the World Dumpling Fest, bringing dumpling styles from around the world to one event. Eastern European, Asian, Latin American, and everything in between, plus cultural performances. Who doesn’t go crazy for dumplings?
Chicago Gourmet
September 24 – 27
Chicago Gourmet returns as the city’s flagship upscale food festival from September 24th to 27th in Millennium Park. The festival features themed tastings like Tacos & Tequila and Hamburger Hop, Grand Cru wine events, brunches, and chef demos. Many of these sessions are ticketed and sell out fast, so plan ahead instead of showing up with fingers crossed.
World Music Festival Chicago
September 25 – October 4
World Music Festival Chicago starts Friday, September 25th, and runs through October 4th, with free concerts from global artists at spots around the city, including the Chicago Cultural Center and Millennium Park. If you like listening to music from other places, you definitely want to check this festival out.
African/Caribbean International Festival of Life / JSVFest
September 25 – 27
The African/Caribbean International Festival of Life, paired with JSVFest, is happening this month from the 25th to the 27th. You’ll enjoy Caribbean and African music, food, arts, and vendors, with a Unity Stage with live performances. The music and food alone make this one of the must-attend festivals of the year!
Randolph Street Market Festival
September 26 – 27
In the West Loop, Randolph Street Market Festival runs Saturday and Sunday from 10am to 5pm. More than one outlet has named it a top 10 flea market in the country, and it’s easy to see why: vintage furniture, clothing, art, vinyl, and design pieces, plus food, bars, and live music. Make a day of it and hit up some West Loop restaurants afterward.
WingOut Chicago
September 26 – 27
WingOut Chicago comes back to Gallagher Way in Wrigleyville that same weekend for its 11th year. There’ll be timed tasting sessions where you sample wings from a bunch of different vendors, vote in flavor competitions, and listen to live music, all right next to Wrigley Field.
Hyde Park Jazz Festival
September 26 – 27
Closing out the month, Hyde Park Jazz Festival hits its 20th anniversary on Saturday and Sunday, September 26th and 27th. It runs from midday into late evening on Saturday and shorter hours on Sunday, mixing Chicago jazz musicians with visiting artists across indoor and outdoor stages. It’s free to attend, but there will be a donation box available if you can spare a few dollars for a good cause.
Final Thoughts
And that’s everything happening in September in Chicago. You’ve got 21 events across four weekends, and that’s before you count the smaller gallery openings, block parties, and neighborhood programming that never quite makes it onto a citywide calendar. We didn’t fit a ton of smaller, local events into this article, but they’re always worth checking out.
If you make it out to any of these festivals and wonder what it’d be like to live in that neighborhood, give us a shout, and we’ll be happy to help. We don’t just know the boundaries on a map. We know which block has the good coffee shop and which one gets loud on festival weekends.
Enjoy the rest of your September, and we hope to run into you enjoying one of these events!
