Chicago September 2020 Events

Spend Labor Day Weekend in Chicago This Year!

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 Chicago Jazz Festival and the Taste of Polonia event! The weather tends to be enjoyed throughout the month as it’s the perfect median between the hot summer and the upcoming chillier months.

September Event Calendar

Chicago Jazz Festival

3-6 Sep, 2020
Millineum Park/ City-Wide
Chicago Jazz Festival

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 Millineum Park to experience the 43rd-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.

African Festival of the Arts

4-7 Sep, 2020
Washington Park MAP

Spend part of your Labor Day weekend in Chicago celebrating African art, crafts, music, food, and entertainment. The 31st 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 for $15; they are $20 at the gate and $5 for children ages 5-12. Family and weekend passes are also available for $40.

Taste of Polonia

4-7 Sep, 2020
Jefferson Park MAP
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 35 bands on four stages, food (such as polska kielbasa, potato pancakes, pierogi), adult beverages, live music, tastings and cooking classes, exhibits, vendors, carnival rides, and more.

Chicago Food Truck Fest

12 Sep, 2020 10:00 am
South Loop, Chicago MAP
Chicago Food Truck Fest

Experience one of America's top food truck festivals by eating with gathered mobile chefs at the Chicago Food Truck Festival! Being that Chicago is commonly referred to as the food and drink capital of the world, you're bound to have an unforgettable culinary experience. General admission is free, but it doesn't include food truck eats. Ten-dollar VIP tickets are available for purchase online; they include 1 free drink ticket.

Lakeview Taco Fest

19-20 Sep, 2020
Southport Avenue (from Addison to Roscoe) MAP

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 are, 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.

Expo Chicago

25-27 Sep, 2020 @ 11:00 am
Navy Pier MAP
Expo Chicago

Attention artists and lovers of the arts: head down to Navy Pier, a 3,300-foot-long pier on the shoreline of Lake Michigan, to experience this popular and respected art exhibition! The International Exposition of Contemporary & Modern Art (Expo Chicago) will feature beautifully curated, aesthetically pleasing, museum-quality art and designs by 135 exhibitors! General admission single-day tickets are $30, $50 with a guided tour included. Three-day admission tickets are $45. 

Bristol Renaissance Faire

11 Jul, 2020 - 7 Sep, 2020
Off I-94 at the IL/WI Border MAP
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 $25.95 and $11.50 for kids 5-12; children under 5 get in for free! 

Chicago Concerts in September

  • 09/29/2020 Six The Musical Broadway Playhouse at Water Tower Place Buy Tickets
  • 09/29/2020 And That's Why We Drink Podcast Thalia Hall Buy Tickets
  • 09/30/2020 Six The Musical Broadway Playhouse at Water Tower Place Buy Tickets
  • 09/30/2020 Six The Musical Broadway Playhouse at Water Tower Place Buy Tickets
  • 09/30/2020 The Dead South House Of Blues - Chicago Buy Tickets

Upcoming Nightclub Events

Mon, Sep 28 at Schubas Sampa The Great
Mon, Sep 28 at Berlin Nightclub Crash Landing
Wed, Sep 30 at Schubas OSHUN