Travel Magazine

12 Upcoming Events for a September to Remember

By Urbanmatter Chicago @UMatterChicago

September might be Chicago’s best month yet

The city is jam-packed with so many events next month, we can barely keep track. It’s typically a hectic time of the year, with students going back to school and businesses ramping up for fall. But it’s also super exciting because it’s that perfect month between summer and fall where the weather’s just right.

Some of the most exciting and in-demand events of the year are taking place next month, and we handpicked some highlights just for you. Here are 12 things to do in September that’ll make next month unforgettable.

Taste of Polonia Festival

september events

Photo Credit: Copernicus Center

September 2 – 4: Celebrate Chicago’s renowned Polish culture at this outdoor festival near the Copernicus Center featuring delicious Polish eats, live music, Polka dancing, carnival rides, and craft vendors.

Windy City Wine Festival

september events

Photo Credit: Everfest

September 9 – 10: Wine? We don’t need to tell you twice. Sip the night away at scenic Millennium Park and learn about varietals from over 300 international vendors as you listen to live music for an evening of ultimate relaxation.

Shock Top Oyster Fest

september events

September 10: Head to Roscoe Village to enjoy an endless supply of delicious gems from the sea, accompanied by Shock Top brews, arts and crafts, and live music.

Little Village Festival

september events

Photo Credit: Red Tri

September 9 – 11: Join Chicago’s vibrant Mexican community in Little Village for a non-stop party that’s got every festival necessity covered. Food, drinks, music, rides, and a massive parade are sure to draw out an awesome crowd.

Throwback Music Fest

12 Upcoming Events for a September to Remember

September 9 – 11: The northwest side is takin’ it back old school with a retro music event that welcomes all ages to have some good ol’ fashioned fun. Rock out to hits from the ’50s, ’60s, and ’70s for a post-Labor Day party.

Venetian Night

september events

Photo Credit: Chicago Harbors

September 10: Hop aboard a cruise ship or chill on the shorelines to watch a dazzling parade of decorated boats pass by in the harbor of Navy Pier under a starry night sky. This is guaranteed to be the most picture-perfect night of the month.

River North Whiskey Festival

september events

September 10: Indulge in fine craft whiskeys, bourbons, and scotches from over 30 different vendors in cool River North for a fun daytime activity. Any opportunity for a tasting is sure to be a good time.

Country Crawl

september events

September 10: Wear your favorite cowboy boots and hat and stomp your way to Wrigleyville for a country-themed bar crawl that’s gonna be big. If country music is your thing, this is one you don’t want to miss.

City Made Fest

september events

Photo Credit: City of Chicago

September 17 – 18: Andersonville is putting the spotlight on any and everything that’s locally made, homegrown, and born and raised. Support Chicago talent and enjoy crafts, drinks, food, and performances you won’t find anywhere else.

EXPO Chicago

september events

September 22 – 25: Attend the peak of Art Week in Chicago and open your eyes to incredible contemporary artwork by leading artists from all over the world. For four days, Navy Pier will be home to this world-class visual celebration.

Oktoberfest Chicago

september events

September 23 – 25: The legendary autumn Bavarian tradition comes to the Windy City with just as much beer as you’d expect. Ring in upcoming October at St. Alphonsus Church with beer, brats, music, and more.

AAHH! Fest

september events

Photo Credit: OOTLyfe

September 24 – 25: Rapper and fellow Chicagoan Common organized a two-day music festival that brings the best of hip-hop and R&B to Union Park while also giving back to Chicago communities by showcasing local talent. Don’t miss it!


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