What To Do in Chicago This September

Summertime in Chicagoland is great, but the fun doesn’t stop in the fall. It may even be argued that things get better in the Windy City in September, as schools get back in session and many people are out enjoying some of the best weather of the year. Check out some great picks with our list below!

Music Festivals (all month)

With life returning to somewhat normal and great fall weather on tap, why not experience an outdoor music fest this September?

We’ll start with the big one first; Pitchfork Music Festival. Happening from Sept 10-12th in Union Park, P4K is surely a big weekend for Chicago music fans. This year’s lineup features acts like Animal Collective, St. Vincent, and Erykah Badu among others. If you’re more into dance and EDM, check out the ARC Festival. Also taking place at Union Park but on Sept 4-5, ARC takes global EDM and house music talent to central Chicago. Finally, for those who wanna rock out, check RIOT Fest. Run The Jewels, Smashing Pumpkins, and the Pixies headline a rock and punk-heavy lineup in Douglass Park on the weekend of 17-19 Sept.


Cubs and White Sox Games (all month)

One of the things many of us missed during the COVID lockdown was live baseball! September is the last month of the MLB regular season, and we would not be doing our duty if we didn’t recommend a trip to the Friendly Confines. That’s the nickname for Wrigley Field, the charming park of the Chicago Cubs. Hit up Wrigleyville (the charming neighborhood surrounding the park) for great eateries and bars as well. We also have to put in a good word for the White Sox! The South Siders are as proud of their team as the North Siders are of theirs, and the Sox are fighting for the top of the AL Central Division this year. Catch games in both ballparks all month long.


Millennium Park Concerts (all month)

Music festivals are nice, but what if you want something a bit more chill or something easier on the budget? Easy answer.

When the weather is nice, Chicago parks can’t be beaten. The Pritzker Pavilion at Millennium Park is a great place to relax. Add some free music and a laid-back atmosphere and the scene is set for fun! The Millennium Park Summer Music Series happens every Monday and Thursday from 6:30–8:30pm until September 16, 2021. Also, Chicago In Tune presents special music at the Pritzker the whole month of September. 

Here’s the schedule:

Gospel: Friday, September 3, 5:30–8:30pm

Jazz: Saturday, September 4, 5:30–8:30pm

House: Saturday, September 11, 5:30–8:30pm

Blues: Saturday, September 18, 5:30–8:30p


Artfest Michigan Avenue (Sept 18th-19th)

One of the best free events on the Magnificent Mile shows 70 juried artists from around the country. A multitude of art is available for both viewing and purchase, so if you need some cool new decor for your place, you might be in luck! Most exhibits take place at the base of the iconic Tribune Building. This year, the organizers recommend free reservations to help spread out the crowds, though walkups are welcome.


Marvel: Universe of Super-Heroes Exhibit, Museum of Science and Industry (Wednesdays-Sundays)

The Marvel exhibit at MSI closes in October, so if you haven’t checked it out yet…what are you waiting for? If you’re a fan of Spider-Man, the Hulk, Black Panther, and the rest, you’ll be in for a treat. Over 300 artifacts including original comic book pages and props from the films exist along with sculptures and displays. The MSI is open Wednesday through Sunday from 9:30 a.m. to 5:30 p.m.


Lakeview Taco Fest (18-19 Sept)

Does anyone else love tacos? If you do, then maybe the Lakeview Taco Fest is for you. Over twelve different Chicago restaurants will cook their favorite styles of tacos here, and it’s up to you to decide which ones are the best. There are also cold beers, live music, and even Mexican-style wrestling happening! Seriously. Admission is $10, and the donation benefits the Friends of Lakeview.


Joffrey Ballet At Ravinia (Friday, September 17th)

It’s world-renowned, it’s magical, and many native Chicagoans have never seen it! Yes, we speak of the Joffrey Ballet company. And the best time to see it is outside at Ravinia. Lawn tickets are only $15, and you can bring your own food and drinks. There’s no better way to see what’s arguably America’s best dance company.


German-American Oktoberfest (Sept 10th-12th)

Yep, pretzels, sausages, and all things Bavarian. Chicago’s German celebration takes place at St. Alphonsus in the West Lakeview neighborhood. There’s a parade at 2pm on Saturday, but the beer and music flow all weekend. Bring your own Lederhosen!



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