Summer in Chicago wouldn’t be the same without its iconic street festivals. Located in vibrant neighborhoods across the city, these local-favorite events are a great way to enjoy the warm weather and block-party vibes while exploring the food, art, and culture that make the city special.
While many of these festivals offer a suggested donation for admission, your donation goes a long way in supporting the participating musicians and artists and helping ensure future events.
Here are the Chicago street festivals not to miss this summer 2025.
May street festivals
As the weather warms up, Chicago neighborhoods begin to buzz with the first of the year’s street festivals. Kick off summer with fests celebrating German culture, local music, and Chicago’s iconic hot dogs.
Lincoln Park Mayfest (May 16 – 18): Kick off summer in the heart of historic Lincoln Park. Experience live music performances, unique art, and food from local restaurants.
Belmont-Sheffield Music Fest (May 23 – 25): The Lakeview neighborhood’s block party is steps from the Belmont ‘L’ station, featuring tribute bands, food and drinks, and creative goods made by local artists.
Randolph Street Market Festival (May 24 – 25): Head to the West Loop for this European-style flea market. Shop thousands of antique and vintage finds, including fashion, jewelry, art, and decor.
Maifest (May 29 – June 1): Celebrate German culture at this annual gathering in Lincoln Square with traditional food, giant beers, and live music.
Windy City Hot Dog Fest (May 30 – June 1): This Portage Park festival will showcase some of Chicago’s most classic hot dog stands, allowing attendees to judge the best frankfurters for themselves.
Do Division Street Fest (May 30 – June 1): Enjoy a variety of West Town food and retail vendors, live music on two stages, and a family-fun space at this summer staple event.
June street festivals
In June, the outdoor events begin in earnest with fun and free festivals filling neighborhood streets and parks every weekend of the month. Mark your calendars for lively art fairs, a celebration of Puerto Rican culture, and the city’s iconic Pride celebrations.
Ribfest Chicago (June 6 – 8): Stop by the North Center neighborhood to sample unforgettable barbecue and listen to live music from top local and national acts.
Lincoln Park Greek Fest (June 6 – 8): Experience Greek heritage at this annual celebration in Lincoln Park featuring authentic food, music, and dancing.
57th Street Art Fair (June 7 – 8): Walk through the city’s oldest juried art fair in Hyde Park, where you can browse the works of up to 200 artists from all over the country.
Puerto Rican Fest (June 12 – 15): Head to Humboldt Park for a celebration of Puerto Rican culture. Enjoy traditional food and drinks, music, a parade, and live performances.
Andersonville Midsommarfest (June 13 – 15): This popular festival highlights the quirky Andersonville neighborhood’s Swedish heritage, LGBTQ+ pride, and local businesses.
Taste of Randolph (June 13 – 15): Sample some of the West Loop’s acclaimed local spots at this food festival and listen to live music.
Old Town Art Fair (June 14 – 15): See works from more than 200 nationally acclaimed artists at this long-running annual event in Old Town Triangle Historic District, celebrating its 75th year in 2025.
Wells Street Art Festival (June 14 – 15): Admire the charm of the Old Town neighborhood while enjoying the works of more than 130 artists, local food, and interactive activities.
Fiesta Back of the Yards (June 20 – 22): This summer celebration spotlights the diversity and rich cultural past of the Back of the Yards neighborhood with live music, dance, and carnival rides.
Chicago Pride Fest (June 21 – 22): Celebrate Pride in Chicago’s landmark Northalsted neighborhood, showcasing the city’s LGBTQ+ life, culture, and community. Catch drag performance, a pet parade, music and dance, and more.
July street festivals
Savor the summer at an array of foodie events, like festivals dedicated to burgers, tacos, and more. And don’t miss exuberant cultural celebrations showcasing African and Chinese heritage.
African/Caribbean International Festival of Life (July 11 – 13): The cultural festival on the South Side celebrates the music, lifestyle, and people of various African and Caribbean nations.
Southport Art Fest (July 12 – 13): Stroll down Southport Avenue in Lakeview to explore unique pieces from more than 100 artists, along with charming boutique shops and local theatres.
West Fest (July 18 – 20): Experience the West Town neighborhood with this street fest full of community retailers and restaurants, live music, and works from local artists and makers.
Roscoe Village Burger Fest (July 18 – 20): Try burgers from top Chicago eateries, from classic to creative, at Roscoe Village’s annual festival featuring live music, arts and crafts, and a zone for kids.
Tacos y Tamales Festival (July 18 – 20): This Pilsen festival, modeled after a traditional Mexican Market, celebrates Chicago’s Hispanic and Latin cultures with traditional food, music, and dance.
Taste of River North (July 18 – 19): In the buzzing River North neighborhood, sample the area’s rich food scene alongside live music and a dog parade.
Chinatown Summer Fair (July 26 – 27): Celebrate Chinese culture at this annual fair in the city’s historic Chinatown. Enjoy traditional dances, live performances, and authentic food.
Wicker Park Fest (July 26 – 28): Head to Wicker Park and explore the neighborhood’s music, local food, and arts and crafts at this local-favorite event.
August street festivals
Round out festival season with exciting events across the city. Check out food festivals showcasing Greek, Italian, Mexican, and Polish cuisines, plus fests dedicated to art, music, and more.
Jeff Fest (Aug. 1 – 2): Spend time at the Jefferson Park Arts & Music festival, an annual neighborhood tradition with inspiring art, tunes, food, and an area for kids.
Northalsted Market Days (Aug. 9 – 10): This huge, joyful festival celebrates the LGBTQ+ community in Chicago’s Northalsted neighborhood with live music on five stages, more than 250 vendors, and dance exhibitions.
Taylor Street Little Italy Festival (Aug. 14 – 17): Get a taste of Chicago’s historic Little Italy at this neighborhood event highlighting Italian culture, food, and more.
Glenwood Avenue Arts Fest (Aug. 15 – 17): This arts-centric fest has taken over the streets of Rogers Park for more than 20 years, with artists, crafters, live music, and more.
Taste of Greektown (Aug. 22 – 24): Sample the best bites from all around Chicago’s vibrant Greektown with lively bands, dance troupes, and tons of traditional food.
West Loop Art Fest (Aug. 23): Browse multiple blocks filled with local art vendors at this annual event in the West Loop, while enjoying live music and entertainment.
Lakeview Taco Fest (Aug. 23 – 24): This weekend fiesta includes everything you need for a perfect summer day — tacos, margaritas, entertainment, and more in the Southport Corridor area.
Taste of Polonia (Aug. 29 – Sept. 1): The country’s largest Polish festival offers authentic Polish food, exhibitions, and cooking classes in the Jefferson Park neighborhood.
September street festivals
Summer may be winding down, but festival season isn’t over yet. Wrap up the season with these fun neighborhood events, including several popular Oktoberfest celebrations.
German-American Oktoberfest (Sept. 5 – 7): Head to Lincoln Square for the neighborhood’s annual Oktoberfest. Delight in German food, drinks, dancing, and entertainment.
Printers Row Lit Fest (Sept. 6 – 7): Find your next read at the South Loop’s annual literary showcase featuring speakers and exhibitors across genres.
Lakeview East Festival of the Arts (Sept. 13 – 14): Stop by Lakeview East for original paintings, sculpture, jewelry, and photography from more than 120 artists in addition to live demonstrations and a garden oasis.
Ravenswood Art Walk (Sept. 13 – 14): The signature event celebrates Ravenwood’s local creative community with open studios and an arts market featuring more than 60 local makers.
St. Alphonsus’s Oktoberfest (Sept. 26 – 28): Say “prost!” at this popular Oktoberfest celebration in Lakeview with a craft beer tasting, live music, and a family activity area.
Hyde Park Jazz Festival (Sept. 27 – 28): This free music festival celebrates the rich tradition of jazz on the city’s South Side, featuring a diverse group of musicians each year.
