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 transition into autumn, September is something to anticipate. Patios are alive and kicking, museums are announcing free days, and all fall’s merriment is beginning to announce itself. On top of that, there are unmissable one-off events like Labor Day celebrations and the Autumn Equinox. Here are the best things to do in Chicago this September!
1. Revel in Labor Day antics
There are loads going on for Labor Day this year, and you can find plenty of options in our roundup of the most memorable things to do this Labor Day weekend in Chicago. Our pick of the bunch, however (if you’re willing to set aside some expenses), has to be a Labor Day sunset cruise.
2. Have an epic weekend at the LIV Golf Individual Championship
Chicago, mark your calendars, because LIV Golf will crown its new Individual Champion from September 13-15 at Bolingbrook Golf Club. Watch two-time major champion Jon Rahm duel breakout star Joaco Niemann, party with DJ and music producer Kaskade, take on fan challenges, and savor street eats—all while soaking in the festival-style vibes.
⛳ Don’t miss out! Learn more and grab your tickets to the LIV Golf Individual Championship now!
3. Head to Arc Music Festival
You might not know, but Chicago has a long history of house music—in fact, its birthplace was here—and this year marks the 40th anniversary of house music. Returning to the heart of the city at Union Park this Labor Day Weekend, August 30 – September 1, ARC’s fourth iteration will be soundtracked by the world’s leading house and techno selectors.
Some of the featured artists in the lineup are Disclosure, Carl Cox B2B Green Velvet, Skepta, Honey Dijon, Charlotte de Witte, Dom Dolla, Sven Väth, Purple Disco Machine, Gorgon City, Kaskade Redux, Jayda G, and LP Giobbi.
When: August 30 – September 1, 2024
Where: Union Park
4. Bites & Vines pairing at The Gwen Hotel
If you’re looking for a night that involves wines, live music, and a curated menu, then head to The Gwen’s Bites & Vines series. Gloria Ferrer, a renowned winery in Sonoma, California, has been celebrated since 1986 as the first sparkling wine house in the Carneros region, and now you can celebrate her wine in Chicago. The Gwen’s Bites & Vines series showcases a curated selection of paired tapas dishes perfectly complemented by Gloria Ferrer wines.
When: Wednesday, September 4 at 6 pm
Where: The Gwen Hotel
5. 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.
When: September 4-6, 2014
Where: Lincoln Square
6. Taste of Chicago
Chicago’s beloved culinary tradition, Taste of Chicago, is back for another year, taking place in Grant Park on September 6 – 8. With 40 food vendors and over a dozen food truck offerings, guests can also enjoy free performances by GRAMMY®-winning CeeLo Green, the celebrated regional Mexican music trio Yahritza y Su Esencia, and the Australian alternative rock group Atlas Genius on the Taste Main Stage.
When: September 6–8, 2024
Where: Grant Park
7. See Elmhurst Art Museum’s Rafael Blanco
Rafael Blanco: Reflecting on a Decade of Public Art marks the first solo museum exhibition of Spanish-born, Aurora-based muralist Rafael Blanco, whose work can be found in cities from California to Maryland, including Illinois murals in Elmhurst, Rockford, Roseville, and Aurora.
The exhibition will feature large-scale, site-specific works transforming the museum’s galleries into a landscape filled with color, texture, and the serendipity of discovering public art in the wild. In addition, Blanco unveils over one hundred self-portraits painted by area students installed in the shape of the US flag, encouraging the next generation to be inspired by their own identities and cultures.
Where: Elmhurst Art Museum, 150 S Cottage Hill Ave, Elmhurst
8. 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.
When: September 15
Where: Ravenswood
9. Concerts Under the Stars
Soak up live music under 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.
When: September 15, 22 & 29
Where: Aire Rooftop Bar
10. Party at Riot Fest
After a confusing name change and venue location, Riot Fest is moving back to Douglass Park in 2024. Those favor the cherished 3-day music festival with an affinity for punk, rock, alternative, metal, and hip-hop who may not be interested in Lollapalooza. With headliners such as Fall Out Boy, Beck, and Slayer, along with other talented acts like Spoon, St. Vincent, and more, it’s bound to be an electrifying weekend.
When: September 20–22, 2024
Where: Douglas Park
11. 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 19-22, nature and architecture melt together for what is known as Chicagohenge.
Chicagohenge happens 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.
When: September 19-22, 2024
12. 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.
When: Saturday, September 28, 2024
13. 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.
14. 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, Field Museum, and the Museum of Science & Industry are offering free admission on select midweek days.
Check out our full guide to free admission days at Chicago’s many museums and attractions.
15. 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. Discover more about these exciting corn mazes here .
16. 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. Discover more about these delightful spots for apple picking near Chicago.
17. 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 more about these exciting spots here.
18. Head to the Bears HQ Viewing Party at Lotties Pub
Attention Chicago Bears fans! Head over to Lottie’s pub, the official Miller Lite Bears HQ Bar, on Sunday, September 29th, at noon to watch the Chicago Bears go up against the Los Angeles Rams. Enjoy special offers such as $4 mimosas, $6 22 oz Miller and Coors Cups, $6 Tullamore Dew Shots, $7 Bloody Marys, and $18 Sausage & Giardiniera pizzas.
19. Discover Chicago’s legendary street art
Chicago’s street art scene is a vibrant tapestry of murals that have become integral to 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.
20. 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.
21. 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. Discover more about these vibrant patios here.