35+ things to do in Chicago this September 2026

While summer may be winding down, there’s no shortage of music festivals, art walks, cultural events, and more throughout September in Chicago.

The month kicks off with a long weekend (check out our Labor Day guide) and wraps up with the first days of autumn (find things to do this fall in Chicago). And there’s plenty to do in between, including tons of festivals and events celebrating National Hispanic Heritage Month, food, culture, music, and film.

Check out these top picks for things to do in Chicago throughout September 2026.

Top events in Chicago this September

Chicago Jazz Festival (Sept. 3 – 6): The oldest of Chicago’s free lakefront music festivals, the Chicago Jazz Festival in downtown Millennium Park is a true bucket list event for jazz fans. This year’s lineup features a mix of established stars and rising talent.

Chicago Labor Day Parade and Eddie Fest (Sept. 5): Celebrate the holiday weekend in the historic Pullman neighborhood with a vibrant community parade that culminates in a free family-friendly festival, featuring music, food, drinks, and games in Steelworkers Park.

Bike the Drive (Sept. 6): Now in its 25th year, Bike the Drive invites riders of all ages and experience levels to cruise along iconic Lake Shore Drive, with sweeping views at every turn. The morning wraps up with a post-ride festival in Grant Park.

El Grito Festival (Sept. 12 – 13): Celebrate Mexican Independence Day in Chicago with this vibrant celebration of Mexican history, culture, and cuisine. The festival features traditional music and dance performances, authentic food and drink from dozens of vendors, artisan markets, and a festive atmosphere.

Explore more: Check out more Mexican Independence Day events and celebrations around the city.

Midway 5K (Sept. 13): Runners and walkers will get the rare opportunity to take over the airfield at Midway International Airport for a family-friendly race day like no other. There will be a 5K run, a 5K walk, and a mile event for kids.

Chicago Live! (Sept. 19 – 20): Navy Pier transforms into a vibrant stage for Chicago’s cultural community at this free performing arts festival representing music, dance, theatre, and more. The event will feature performances from more than 100 artists and groups, all open to the public.

Chicago Exhibition Week (September 14 – 20): Art lovers can explore more than fifty galleries and cultural spaces during this week-long celebration of Chicago’s thriving contemporary arts scene. Check the calendar for special programs, exhibition openings, artist conversations, and more.

Reeling Film Festival (Sept. 17 – 27): The second-longest-running LGBTQ+ film festival in the country, Reeling brings a diverse lineup of films that spotlight queer stories and underrepresented voices in cinema.

Englewood Jazz Festival (Sept. 17 – 19): For more than 25 years, the Englewood Jazz Festival has delivered three days of free, live music that highlights the long legacy of jazz on Chicago’s South Side and beyond.

International Greeter Day (Sept. 19): The Chicago Greeter program celebrates International Greeter Day with a full day of free pop-up walks. Meet in downtown Millennium Park before heading out to explore one of the city’s diverse neighborhoods with a friendly local.

Riot Fest (Sept. 18 – 20): One of Chicago’s most anticipated annual music festivals returns to Douglass Park with a powerhouse lineup featuring Twenty One Pilots, Iggy Pop, Morrissey, Alanis Morissette, and many more across multiple stages. The festival also features carnival rides, art installations, and a full schedule of after-shows.

Chicago Gourmet (Sept. 23 – 27): Chicago Gourmet, the city’s premier upscale food festival, brings together some of the city’s best culinary talent for a jam-packed weekend of tastings, demonstrations, and unforgettable bites in Millennium Park and beyond.

World Music Festival (Sept. 25 – Oct. 4): This annual festival showcases music and genres from around the world, with shows all around the city. The center of the festival takes place at the Chicago Cultural Center.

More events in Chicago this September

Summer fireworks at Navy Pier (Sept. 2 and 5): Don’t miss your last chance to catch the free Navy Pier fireworks before the summer season ends. The show lights up the sky every Wednesday and Saturday, with the Chicago skyline and Lake Michigan serving as the stunning backdrop.

The Great American Lobster Fest (Sept. 5 – 6): Fresh Maine lobsters are flown daily to Navy Pier for this lakefront seafood festival, featuring whole lobsters, lobster rolls, chowder, and more just steps from Lake Michigan. The fest also includes live music, cold drinks, and a full weekend of waterfront festivities.

Sound of Gravity (Sept. 3 – 6): Experience a boundary-pushing arts festival filled with immersive performances, live music, and interactive installations that highlight Chicago’s experimental creative scene.

North Coast Music Festival (Sept. 4 – 6): Dance the weekend away at this multi-day music fest, bringing the best in EDM, house, hip-hop, techno, and more to SeatGeek Stadium in nearby Bridgeview.

Taste of Polonia (Sept. 4 – 7): Get a taste of Chicago’s vibrant Polish heritage at the country’s largest Polish festival. Enjoy four days of live music, family activities, and of course, endless Polish cuisine, from pierogi to kielbasa and beyond.

79th Street Renaissance Festival (Sept. 6): This popular community festival is Auburn Gresham’s biggest and longest-running neighborhood tradition, featuring live entertainment, food, family fun, and local culture.

Throwback Music Festival (Sept. 11 – 13): Go back in time through five decades’ worth of iconic music, from classic rock and Motown to funk and pop. The lineup spans generations and genres, making for a fun and nostalgic outing for music fans of all ages.

German American Oktoberfest (Sept. 11 – 13): Oktoberfest comes to the heart of Lincoln Square, a neighborhood with deep German roots. This free street festival brings German food, beer, traditional music, folk dancing, and plenty of old-world charm.

Chicago Football Classic (Sept. 12): The Chicago Football Classic returns to Soldier Field, with Mississippi Valley State University taking on Lincoln University. There will also be a career fair connecting students with historically Black colleges and universities.

Printer’s Row Lit Fest (Sept. 12 – 13): One of the largest and oldest literature festivals in the Midwest, this free event features author readings, book signings, panel discussions, and hundreds of booksellers in the historic Printer’s Row area.

Ravenswood Art Walk (Sept. 12 – 13): More than 50 local artists will share their work through open studios, pop-ups, and an outdoor market during the Ravenswood Art Walk weekend.

Renegade Craft Fair (Sept. 12 – 13): Shop more than 400 independent makers, artists, and designers from Chicago and beyond. Browse a thoughtfully curated selection of handmade goods spanning jewelry, clothing, ceramics, and art prints.

Old Town Oktoberfest (Sept. 18 – 20): The charming streets of Old Town come alive with the sights, sounds, and flavors of Bavaria at this Oktoberfest celebration. Expect steins of German beer, bratwurst and schnitzel, traditional folk music, and lively stein-holding contests.

Retro on Roscoe (Sept. 18 – 20): A tradition for more than 30 years, this Roscoe Village throwback extravaganza is packed with live music, a classic car show, vintage shopping, and old-school fun for all ages.

Lakeview East Festival of the Arts (Sept. 19 – 20): This annual arts festival showcases more than 150 artists and their work, spanning photography, furniture, jewelry, paintings, and more. There will also be plenty of kid-friendly activities, live music, and food and drink options.

Jack’s Pumpkin Pop-Up (starts September 19): Chicago’s most over-the-top Halloween experience is back, and it’s bigger than ever. Jack’s Pumpkin Pop-Up features a giant corn maze, carnival games, axe throwing, food trucks, and an abundance of pumpkin-themed fun across a sprawling outdoor venue.

World Dumpling Festival (Sept. 19 – 20): With a new location in Lincoln Park, the World Dumpling Festival celebrates Chicago’s international culinary scene through the universal language of dumplings, from bao and pierogi to empanadas and gyoza.

Rhinoceros Theater Festival (Sept. 20 – Oct. 29): A tradition in the city’s independent theatre community for more than three decades, the Rhinoceros Theater Festival is Chicago’s longest-running fringe theatre event.

Chicago River Swim (Sept. 20): Now in its second year, the Chicago River Swim is already becoming one of the city’s most talked-about fall traditions. Spectators can cheer on swimmers along the Chicago Riverwalk from Lake Street to State Street.

Chicago Wellness Week (Sept. 21 – 27): This inaugural citywide wellness festival focuses on health, movement, and community. Check out everything from yoga and Pilates to mental health panels and nutrition workshops.

Chicago Underground Film Festival (Sept. 23 – 27): The longest-running underground film festival in the world shines a spotlight on the defiantly independent filmmaker. Screenings cover documentaries, world premieres, and experimental formats.

African/Caribbean International Festival of Life (Sept. 25 – 27): This Washington Park festival is dedicated to the culture and traditions of African and Caribbean nations. Enjoy three days of live music, traditional dance, authentic cuisine, and artisan vendors representing the diversity of the African diaspora.

Hyde Park Jazz Festival (Sept. 26 – 27): This legendary free jazz festival takes over historic Hyde Park with non-stop performances all weekend, featuring a mix of Chicago jazz legends and rising stars across multiple neighborhood venues.

Beverly Art Walk (Sept. 26): The annual Beverly Art Walk showcases a variety of local artists and their work through local demonstrations, home studio tours, and permanent public art throughout the Beverly neighborhood.

WingOut Chicago (Sept. 26 – 27): WingOut Chicago is back in Wrigleyville for the city’s ultimate chicken wing cookout, with creative and craveable flavors from the city’s top wing purveyors.

Randolph Street Market (Sept. 26 – 27): Browse vintage finds, antiques, and local artisan goods at this bustling European-style market in the West Loop neighborhood.