While summer may be winding down, there’s no shortage of street festivals, art walks, museum exhibits, 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, music, and film.
Check out these top picks for things to do in Chicago throughout September 2025.
Top events in Chicago this September
Taste of Chicago (Sept. 5 – 7): The summer’s biggest free-admission food festival returns to Grant Park for a weekend full of eats, drinks, and live music, highlighting the city’s vast array of cuisines.
International Greeter Day Celebration (Sept. 6): This pop-up celebration of local connection and culture features free tours of Chicago’s vibrant neighborhoods, led by friendly locals.
Pullman Labor Day Parade (Sept. 6): This parade and festival honor the historic Pullman community’s role in the national labor movement.
79th Street Renaissance Festival (Sept. 6): This year marks the 20th anniversary of Auburn Gresham’s biggest and longest-running neighborhood festival, featuring live entertainment, food, family fun, and local culture.
Sunday in the Park with Lyric (Sept. 8): Pack a picnic and enjoy an evening of free opera in Millennium Park as members of the Lyric Opera perform beloved classics with skyline views to boot.
El Grito Festival (Sept. 13 –14): In commemoration of Mexican Independence Day, head downtown to Grant Park for this vibrant celebration of Mexican history, culture, gastronomy, and more.
Riot Fest (Sept. 19 – 21): Enjoy the annual festival in Douglass Park featuring headlining performances from Blink 182, Alkaline Trio, Weird Al Yankovic, and more.
Chicago Architecture Biennial (starting Sept. 19): Explore cutting-edge projects and ideas from global contributors at North America’s largest architecture and design festival.
Chicago Exhibition Weekend (Sept. 19 – 21): Fifty galleries and cultural spaces across the city unite to spotlight Chicago’s thriving arts scene with special programs and exhibitions.
Día de Muertos: A Celebration of Remembrance (opens Sept. 19): The National Museum of Mexican Art is holding their annual exhibit dedicated to Day of the Dead customs and traditions.
Reeling: Chicago LGBTQ+ International Film Festival (Sept.19 – 28): The second-longest-running film festival of its kind in the world, this event showcases a diverse range of genres and queer experiences.
Chicago Live! (Sept. 20 – 21): Navy Pier hosts this two-day performing arts festival featuring more than 100 music, dance, and theatre groups from across Chicago’s cultural community.
Chicago Gourmet (Sept. 25 – 28): Food and drink lovers won’t want to miss a jam-packed schedule of events for Chicago Gourmet, featuring some of the nation’s top chefs and restaurateurs.
World Music Festival (Sept. 26 – Oct. 5): This annual festival showcases the sounds of music and genres from around the world, with shows all around the city.
Hyde Park Jazz Festival (Sept. 27 – 28): This free music festival takes over its namesake neighborhood with non-stop jazz performances all weekend long.
Randolph Street Market (Sept. 27 – 28): Browse vintage finds, antiques, and local artisan goods at this bustling European-style market.
More events in Chicago this September
Rhinoceros Theater Festival (Sept. 4 – 28): Now in its 36th year, Rhinoceros Theater Festival is Chicago’s longest-running fringe theatre event.
Green City Market Chef BBQ (Sept. 4): Now in its 25th year, this culinary event brings together 100 of Chicago’s top restaurants, winemakers, brewers, and more.
Edgewater Music Festival (Sept. 5 – 7): The first-ever Edgewater Music Festival will include live music, local food vendors, family activities, and an artisan market showcasing the best of this lakefront enclave.
Throwback Music Festival (Sept. 5 – 7): Gladstone Park is home to the Throwback Music Festival, highlighting five decades worth of iconic music all weekend long.
German American Oktoberfest (Sept. 5 – 7) Oktoberfest is in full swing in the heart of Lincoln Square, with a free festival featuring German food, drinks, dancing, entertainment, and more.
Mandala Makers Festival (Sept. 5 – 7): This community arts festival features performances, workshops, and exhibits by Chicago’s diverse and emerging South Asian artists.
Printer’s Row Lit Fest (Sept. 6 – 7): This year marks the 40th anniversary of one of the largest and oldest literary festivals in the country, spanning five blocks in the historic South Loop neighborhood.
Renegade Craft Fair (Sept. 6 – 7): The maker-centric market heads to Wicker Park for a weekend filled with hundreds of curated local artists showcasing their work.
Tails on the Trails (Sept. 7): Bring your pup for a dog-friendly day at Morton Arboretum, complete with wooded trails, pet-focused vendors, and fun activities for furry friends.
Sound & Gravity (Sept. 10 – 14): Experience a boundary-pushing arts festival featuring immersive performances, live music, and interactive installations that highlight Chicago’s experimental creative scene.
Englewood Music Festival (Sept. 13): This year is the fifth edition of this free music festival in the Englewood neighborhood. There will be local artist performances, food, retail vendors, youth activities, and much more.
Ravenswood Art Walk (Sept. 13 – 14): The vibrant Ravenswood neighborhood hosts this annual art walk, which features 50+ local artists sharing their work across open studios, pop-ups, and an outdoor market.
Lakeview East Festival of the Arts (Sept. 13 – 14): This popular neighborhood arts festival showcases more than 120 artists and their work, including photography, furniture, jewelry, paintings, and much more.
West Loop Arts Festival (Sept. 20 – 21): This dynamic festival transforms five blocks of Fulton Street into an open-air art gallery and music venue.
Black Wall Street Chicago Festival (Sept. 13): Head to the Woodlawn neighborhood for a local cultural festival celebrating youth, community, music, art, and more.
Ghan-Again Music Festival (Sept. 13): This free, family-friendly celebration of Ghanaian and West African music and culture brings the community together for performances, crafts, food, and more.
Food Truck Festival:(Sept. 13): Taste your way through Chicago’s most popular food trucks serving everything from gourmet tacos to sweet treats at this inaugural South Side festival.
Chicago Underground Film Festival (Sept. 17 – 21): The longest-running “underground” film festival in the world is designed to showcase the defiantly independent filmmaker.
CLINK Wine & Spirits Festival (Sept. 21): Bridgeport Art Center hosts this wine-centric event with more than 50 minority-owned wine and spirits brands on display.
Oktoberfest at the Zoo (Sept. 21): Kick off fall with a special Oktoberfest celebration at the historic Lincoln Park Zoo, with plenty of German-inspired food and drinks.
Beverly Art Walk (Sept. 27) The charming Beverly neighborhood is hosting their annual, with local demonstrations, home studio tours, and public art throughout the Beverly neighborhood.
Movies at Gallagher Way (through September): Outdoor movies are still going strong outside Wrigley Field, with upcoming screenings of Space Jam and Remember the Titans.
