Fall Fun in Chicago

September 4, 2023 | Things to Do

Summer may be winding down, but there’s no shortage of things to do this September in Chicago. And what better way to kick off Fall than with the long Labor Day weekend ahead. Check out the Labor Day guide and find things to do this fall in Chicago from our local tourism bureau, Choose Chicago.  Here is a list of a few fun activities happening this month.

Wing Out Chicago (Sept. 2 – 3): Get a taste of the city’s best wings at this outdoor fest in the shadow of Wrigley Field.

Bike the Drive (Sept. 3): Bring your bike (or rent one) for the annual Bike the Drive, where bikers of all skills and ages take over Lake Shore Drive for a car-free route filled with sweeping city views.

Taste of Polonia (Sept. 1 – 4):  This Labor Day weekend taste fest in Chicago is an annual treat.  Great food, music, vendors and fun for the whole family.

Taste of Chicago (Sept. 8 – 10): One of the summer’s biggest food festivals returns to Grant Park for a weekend full of eats, drinks, and live music, highlighting the city’s vast array of cuisines.

Oktoberfest in Lincoln Square (Sept. 8): Oktoberfest is in full swing in the heart of Lincoln Square, with a free festival featuring food, drinks, dancing, and German-American heritage.

World Dumpling Fest (Sept. 9): Who doesn’t love dumplings? Sample dumplings from over a dozen local restaurants representing a variety of international cuisines.

Lakeview East Festival of the Arts (Sept. 9 – 10): In its 18th year, this Lakeview festival showcases more than 150 artists and their work, including photography, furniture, jewelry, paintings, and much more.

79th Street Renaissance Fest (Sept. 9): Check out Auburn Gresham’s summertime celebration, featuring over 100 local vendors and lots of live music.

Printers Row Lit Fest (Sept. 9 – 10): This year celebrates the 38th annual of one of the largest and oldest literary festivals in the country, featuring tons of speakers and exhibitors.

Renegade Craft Fair (Sept. 9 – 10): This popular craft fair heads to its summer spot of Wicker Park for a weekend filled with hundreds of curated local artists showcasing their work.

Mexican Independence Day Parade (Sept. 16): This joyous procession will march through the heart of Little Village to celebrate Mexican identity and culture.

Reader Gala 11/30/2022

Riot Fest (Sept. 15 – 17): Enjoy this annual music festival in Douglass Park featuring headlining performances from Foo Fighters, The Cure, The Postal Service, and Death Cab for Cutie.

Chicago Gourmet (Sept. 21 – 24): Food and drink lovers won’t want to miss a jam-packed weekend of Chicago Gourmet, which brings together some of the city’s best and brightest culinary stars.

Chicago Live! at Navy Pier (Sept. 23 – 24): Visit iconic Navy Pier for the third annual Chicago Live! performing arts festival, featuring over 80 diverse acts across three performance stages.

Hyde Park Jazz Festival (Sept. 23 – 24): The popular free festival takes over its namesake neighborhood with non-stop jazz performances all weekend long.

Reeling Film Festival (Sept. 21 – Oct. 28): This year is the 41st edition of this acclaimed festival, which showcases a variety of LGBTQ+ films and filmmakers.