If you enjoy basking in the sun, September might be a glum reminder that cooler air is approaching. However, if you appreciate the fall foliage and the transition into autumn, September is something to look forward to. Patios are alive and kicking, museums are announcing free days, and all fall’s revelry is beginning to announce itself. Additionally, there are unmissable one-off events, such as Labor Day celebrations and the Autumn Equinox. Here are the best things to do in Chicago this September!
Head to Arc Music Festival
You may not know, but Chicago has a rich history of house music—in fact, its birthplace was here. Returning to the heart of the city at Union Park this Labor Day Weekend, August 29 – August 31, 2025, ARC’s fourth iteration will be soundtracked by the world’s leading house and techno selectors.
🗓️ Dates: August 29 – August 31, 2025
📍 Location: Union Park
German American Oktoberfest
While Chicago isn’t Germany, and we’re a long way from the Hofbräu Haus, you’ll still find authentic German food and traditional drinks at the German American Oktoberfest. Dance to the music of German bands, spend the evening with friends, and enjoy a fabulous festival.
🗓️ Dates: September 5—7, 2025
📍 Location: Lincoln Square
Celebrate everyone’s favorite caffeinated cocktail with an espresso martini bar crawl
Espresso Martini Fest is back for another year, thanks to Mr Black! This year, even more of Chicago’s hottest bars are taking part. From September 29 to October 5, you can discover new interpretations of this iconic cocktail with each bar bringing something different to the festival.
🗓️ Dates: September 29 – October 5, 2025
Taste of Chicago
Chicago’s beloved culinary tradition, Taste of Chicago, is back for another year, taking place in Grant Park on September 5–7. With 40 food vendors and over a dozen food truck offerings, guests can also enjoy free performances.
🗓️ Dates: September 5–7, 2025
📍 Location: Grant Park
Ravenswood Artwalk
We love art in Chicago, and if you think you’ve seen it all, think again. Ravenswood ArtWalk (RAW) is a weekend-long celebration of our local creative community. It features open studios and galleries, pop-up performances and activations, and an outdoor art market featuring 50+ local makers, live music and dance, food trucks, and a Malt Row beer garden.
🗓️ Dates: September 13-14, 2025
📍 Location: Ravenswood
Concerts Under the Stars
Soak up live music under the stars at these nostalgia-filled tribute concerts at Aire Rooftop Bar! This month, the lively concerts will pay homage to Frank Sinatra and Amy Winehouse. Get ready to kick back with a cocktail and enjoy light bites, live music, and unmatched views of the Chicago skyline. Snag tickets here.
🗓️ Dates: September 21, 2025
📍 Location: Aire Rooftop Bar
Chicago’s legendary rock festival returns in 2025 with superstar acts
Chicago’s iconic Riot Fest celebrates its 20th anniversary this fall, packing Douglass Park with unforgettable performances from Green Day, Blink-182, Weezer, and more.
Headlining acts also include Jack White, The Beach Boys, and the enigmatic Weird Al Yankovic.
📍 Location: Douglass Park, North Lawndale, Chicago
🗓️ Dates: September 19–21, 2025
Marvel at the magical autumn Chicagohenge
One of the best things to do in Chicago in September doesn’t occur until later this month. From September 22 to 25, 2025, nature and architecture merge for what is known as Chicagohenge.
Chicagohenge occurs twice a year when the Sun directly aligns with Chicago’s east-west-facing streets. This phenomenon occurs because Chicago’s grid system lines up almost perfectly from north to south and east to west, causing the sun to align directly with these streets and shine down the heart of the city, creating a stunning sight.
🗓️ Dates: September 22–25, 2025
Randolph Street Market Festival
Calling all vintage lovers. This festival features 200 top independent vendors, makers, dealers, and designers across America. Randolph Street Market features an ultra-curated, high-quality selection of antiques and modern goods ranging from fashion to art, jewelry, décor, retro home furnishings, and more.
🗓️ Dates: Saturday, September 27—28, 2025
Embrace the peak of patio season
Despite the end of summer on the horizon, one of the best things to do in Chicago in September is still reveling in the sun on a patio. We’ve rounded up the very best patios in Chicago to give you an endless range of options.
Enter a Chicago museum for free in September
During the summer months, when Chicago’s tourism industry is thriving, it’s rare to find free admission days. However, as we move into the fall months, many of our marvelous museums and attractions begin to offer more frequent free admission days. This September in Chicago, both the Shedd Aquarium, the Field Museum, and the Museum of Science & Industry are offering free admission on select midweek days.
Get Lost In An Epic Corn Maze Near Chicago
Explore the best Chicago corn mazes this fall and immerse yourself in a variety of intricate labyrinths. From the world’s largest corn maze at Richardson Adventure Farm to the spooky thrills of Heap’s Haunted Corn Maze, there’s something for everyone. Whether you’re looking for a family-friendly outing or a challenging adventure, these mazes offer a perfect autumn escape.
Go Apple Picking Near Chicago
Experience the joy of apple picking this weekend at some of the best orchards near Chicago. There’s something for everyone, from the unique apple maze at Royal Oak Farm to the family-friendly activities at Kuipers Family Farm. Whether you’re after Honeycrisp, Galas, or Granny Smith, you’ll find a variety of apples to pick. For a more traditional experience, visit the no-frills Heinz Orchard.
Chicago Pumpkin Patches for a Spooky Season
Experience the essence of fall by visiting some of the best pumpkin patches in Chicago this weekend. From the unique Pumpkin-Eating Dinosaur at Goebbert’s Pumpkin Patch to the sprawling 12-acre Jonamac Orchard, these locations offer a variety of activities for everyone. Whether you’re looking to pick the perfect pumpkin or enjoy a hayride, these patches provide a quintessential fall experience.
Discover Chicago’s legendary street art
Chicago’s street art scene is a vibrant tapestry of murals that have become an integral part of the city’s identity. These artworks, crafted by both renowned and emerging artists, are more than just visual spectacles; they celebrate diverse heritages, advocate for equality, and honor societal heroes. With new pieces appearing regularly, these murals are a must-see for anyone exploring the city. For a detailed guide to the most unique murals in Chicago.
Sip drinks at our favorite rooftop bars in Chicago
As the warm weather arrives, it’s time to explore the city’s vibrant rooftop bar scene. From chic restaurant terraces to lively lounges, Chicago offers a variety of stunning rooftops perfect for socializing with friends. Whether you’re looking for panoramic views or a lively atmosphere, these rooftop bars are a must-visit. Discover more about the top spots for a refreshing drink and a great view at Chicago’s best rooftop bars.
Check out an essential fall patio in Chicago
Chicago doesn’t play around when it comes to patio season. With options ranging from riverside oases to multi-tiered patios, the city offers a diverse array of outdoor dining experiences. Whether you’re looking for a lively bohemian vibe or a serene riverside setting, Chicago’s patios provide the perfect backdrop for enjoying al-fresco dining. Explore the best patios in Chicago to find your ideal spot for a delightful outdoor meal this weekend.
