Division Street in West Town comes alive with live music, food, boutique sales, fashion shows and family fun with the annual Do Division Street Fest on May 29-31, 2026. One of the most anticipated summer music fests, Do Division Street Fest serves up an astonishing selection of local … [Read more...] about Do Division Street Fest
Chicago festivals
Celebrate German Culture at Chicago Maifest
Welcome spring at the traditional German celebration of the season, Maifest Chicago. The 26th annual festival runs from May 29 -31, 2026, in the heart of Chicago's German community in Lincoln Square. Chow down on lots of German food and witness a traditional keg tapping, maypole dancing … [Read more...] about Celebrate German Culture at Chicago Maifest
Andersonville Midsommarfest
One of the most beloved summer events is when the Andersonville neighborhood celebrates its Swedish heritage and culture with the 60th annual Andersonville Midsommarfest, from June 12 through June 14, 2026. One of Chicago's oldest and most anticipated street festivals, Andersonville … [Read more...] about Andersonville Midsommarfest
Free American Writers Festival
Celebrate the breadth and depth of the art of writing at the third annual American Writers Festival on June 6-7, 2026, at the American Writers Museum and the Harold Washington Library Center. The weekend of free programming will feature more than 90 writers. Sponsored by the … [Read more...] about Free American Writers Festival
Things To Do In Chicago in May
With spring weather warming up more consistently and the lakefront thawing into lovely aquamarine waves, May is a favorite time to explore Chicago before the large summer tourist crowds arrive. Consider these free or low-cost activities for your Chicago May adventures. Besides the essential … [Read more...] about Things To Do In Chicago in May
Belmont-Sheffield Music Fest
For many neighborhood festival fans, the Summer fest season officially kicks off with the cover band glory of the Belmont-Sheffield Music Festival, set for May 22-24, 2026. The 40th annual celebration of community and local musicians draws enthusiastic crowds to the streets near the … [Read more...] about Belmont-Sheffield Music Fest
Chicago Mayfest in Lincoln Park
Beer, food and cover bands are the hallmarks of the city's first festival of the summer, Chicago Mayfest. This year's 29th annual edition continues the tradition from May 15-17, 2026, in the Lincoln Park neighborhood. This year's fest will kick off at Armitage and Sheffield and … [Read more...] about Chicago Mayfest in Lincoln Park
Sor Juana Festival Events
The annual Sor Juana Festival honors the historic Mexican writer, feminist and nun, Sor Juana Inés de la Cruz, with a dynamic line-up of artists, writers, filmmakers and singers at the National Museum of Mexican Art through April 29, 2026. Check out some of the exciting free … [Read more...] about Sor Juana Festival Events
Chicago Magnificent Mile Lights Festival
Chicago's iconic Michigan Avenue will shine even brighter during the 31st annual Magnificent Mile Lights Festival on November 22, 2025. This beloved holiday tradition combines a parade, lights, music, tree lighting and family activities for joy-filled holiday fun. The event kicks off at … [Read more...] about Chicago Magnificent Mile Lights Festival
Destinos Chicago Latino Theater Festival
Celebrate Latino theater and dramatic creativity at the eighth annual Destinos: Chicago International Latino Theater Festival for an entire month, from October 1 to November 2, 2025. , at theaters across the city. The Chicago Latino Theater Alliance presents this anticipated annual … [Read more...] about Destinos Chicago Latino Theater Festival
Riverwalk Fall Fest
Experience the beauty of the fall season with the Chicago River as the backdrop at the Island Party Hut Fall Fest on the Chicago Riverwalk on Saturdays, September 20-October 25, 2025. Enjoy autumn festivities like hay rides on the river, pumpkin patches and eating apple cider donuts along the … [Read more...] about Riverwalk Fall Fest
Lincoln Square Ravenswood Apple Fest
Enjoy Fall fun with apple-inspired food, drinks and artisan goods at the Lincoln Square Ravenswood Apple Fest, October 3-5, 2025. Celebrate the new season with a bounty of edible goodness. Midwest farms will be serving up fresh apples and related dishes and local restaurants and food … [Read more...] about Lincoln Square Ravenswood Apple Fest
