8 Fun Things to Do in Chicago This September, 2021

Make the most of your Chicago summer by exploring some of the best events of the season happening through September. Seltzer shops, an opening with ThinkFoodGroup’s Pigtail, and sporting events are all happening next month. You won’t want to miss these top fun things to do in Chicago this September, especially since summer is coming to an end! 

Andros Taverna’s Week-long Wine and Seafood Event – Aug. 17-25

Travel through the Greek Islands via Chicago with a trip to Andros Taverna August 17-25 for their week-long wine and seafood spectacular.  Experience Wine Director Kristin Franceso’s special selection of Greek wines paired with top-quality seafood prepared by Chef Doug Psaltis including lobsters, blue mussels, razor clams, crystal blue prawns, langoustines and jumbo scallops in the shell. Take a peek at the specially selected  wines for the event: 

  • Santorini — Hatzidakis Familia ‘18
  • Cephalonia — Sclavos Robolla ‘19
  • Crete — Douloufakis “Dafnios” ‘19

Reserve your ticket to Greece now while you still can! 



On your left! Bring your party of six to Recess this Labor Day and make sure one of them knows how to ride a bike. If you are searching for things to do in Chicago in September, you can work with your friends to mix your own margaritas on Recess’ brand-new Fender Blender bike, which serves up to six people. You’ll work up a little sweat and what better way to cool off than perfectly blended margaritas by your best bike-riding friend?

You’ll also enjoy being out on Chicago’s largest outdoor patio one last time for Summer 2021. While you watch your friend take one for the team, be sure to look for all the outdoor murals along the patio and see how many you can find!  Learn how you can reserve your party’s table now for Labor Day by visiting https://www.chicagoinrecess.com.



Logan Square’s new Midwestern salumeria launches dinner service every Friday, Saturday and Sunday for diners. Available weekends from 5:30 to 10 p.m, the dinner menu features dishes like their signature Lardon Salad, a decadent Crispy Duck Leg Confit, and a mouthwatering Steak Frites. Reservations are available on Resy. This new dinner service adds onto Lardon’s daily offerings, including coffee and pastries starting at 7 a.m., lunch from 11 a.m. to 4 p.m. and house-cured meat and artisanal cheeses until close.

St. George Spirit’s Dinner at SepiaSept. 22

St. George Spirits Master Distiller Lance Winters visits Sepia in Chicago for an exclusive one-night-only dinner and discussion on September 22. If you are looking for fun things to do in Chicago, Chefs Andrew Zimmerman and Kyle Cottle have collaborated with Sepia’s Keith Meicher, head bartender, to create a four-course cocktail-paired dinner that highlights the complex flavors of St. George’s spirits. Meicher will craft a cocktail for each course, playing with unique flavors such as basil, peach and chanterelle mushrooms. Winters will be on hand to discuss his passion for creative imaginative artisan spirits while guests enjoy their meal. Tickets are available, but selling fast on Tock.

Drink and Donate to The Greater Chicago Food DepositorySept. 15-19

Bar Roma, located in Andersonville, will celebrate Negroni Week with a trio of craft cocktails, available September 15-19. Mixologist Devin Colloton’s libations include Blonde Negroni, Boulevardier and Sbagliato ($13 each). A portion of the proceeds from each drink will benefit The Greater Chicago Food Depository. Pair your Negroni with Chef Fred Ramos’ Italian cuisine, including summer squash bruschetta, manzo meatballs, baked eggplant parmesan, classic cacio e pepe, veal milanese and more. The complete menu may be viewed here

Bar Roma is open Sunday, Wednesday and Thursday, 5-10 p.m.; Friday and Saturday, 5-11 p.m. For table reservations, visit BarRomaChicago.com.

Negroni Week Menu

$13 each

  • Blonde Negroni- Gin, Cocchi Americano, Dolin Dry Vermouth
  • Boulevardier- Rye, Cocchi Sweet Vermouth, Campari 
  • Sbagliato- Campari, Cocchi Sweet Vermouth, Prosecco

Kick It Down in Bridgeview for Chicago House Athletic Club Home Match No. 3 and No. 4

7000 S Harlem Ave, Bridgeview, IL 60455

Chicago House Athletic Club’s inaugural fall season continues on into September with four total matches, including two at home at SeatGeek Stadium in Bridgeview. A fun thing to do in Chicago in September may consist of traveling down Harlem Ave to watch live sporting events with Chicago’s hottest new sports team:

September 17th | 7:35 PM | Los Angeles Force |

September 24th | 7:35 PM | Michigan Stars Football Club | 

The House started their season with a loss at Detroit City FC but bounced back strong against Stump Town AC with a 1-0 victory and the first three points in team history. Follow UrbanMatter Chicago for more information, stories, and interviews with Chicago House AC players, coaches, and front office personnel.

Cincinnati Bengals @ Chicago Bears | 2021 Home Opener at Soldier Field

High anticipation for a Chicago Bears season is something this city hasn’t been used to in recent years. However, with the arrival of Justin Fields, the city is buzzing. Now whether or not Fields is on the, well, field, come Week 3 when the Bears host the Cincinnati Bengals in their home opener remains to be seen one thing is for certain, Soldier Field is the place to be on September 19th.

Even if you just head down to the South Lot to tailgate, the Bears home opener is a must-attend September activity for all Chicagoans. For more on the Chicago Bears season, their fantasy football prospects, and more, follow UrbanMatter Chicago and Drew Kries.

Go Talk with Neil deGrasse Tyson at the Chicago Theater

It was almost an entire year between shows at the Chicago Theater. One of Chicago’s most iconic destinations was shut down due to COVID-19 and recently opened back up to the world. What better way to celebrate this than Neil deGrasse Tyson and his Cosmic Collisions show to The Chicago Theatre on September 19.

“All the things that go bump in the night (and in the day). And yes, the universe wants to kill you: On occasion these collisions — asteroid & comet impacts on Earth, render life extinct. Learn why and how this happens, and what we are doing about it.”

Photo by Clay Banks on Unsplash