Roaming through car-free streets is one of the joys of Chicago street fests and just because the summer is over doesn't mean you can't still experience this favorite pastime. Head to the Wicker Park neighborhood for the Meet Me on Milwaukee event, where the busy intersection of Milwaukee at … [Read more...] about Free Meet Me on Milwaukee
Music
Free Pumpkin Party at Gallagher Way
Go pumpkin hunting, dance to live music, create arts and crafts and enjoy the season at Gallagher Way's annual Pumpkin Party on October 25, 2025, in the Wrigleyville neighborhood. Bring the kids for a fun-filled day of costumes, trick-or-treating and non-stop activities. The Old Town … [Read more...] about Free Pumpkin Party at Gallagher Way
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
Discount Tickets for The Other Art Fair
Enjoy the thrill of affordable, original art, immersive installations, performances and DJs at The Other Art Fair in the Ravenswood neighborhood, October 30- November 2, 2025. By literally reframing the art experience, The Other Art Fair avoids elitism and makes art accessible and welcoming for … [Read more...] about Discount Tickets for The Other Art Fair
Arts in the Dark Halloween Parade
Head to State Street to celebrate Halloween as the "artist's holiday" with an evening of wonder and creativity at the Arts in the Dark Halloween Parade on October 18, 2025, in the Loop. Recognized as one of the top six Halloween events in the world, the tenth annual Arts in the Dark parade … [Read more...] about Arts in the Dark Halloween Parade
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
Free World Music Wednesday Concerts
The new season for World Music Wednesday has been announced! Every Wednesday, through December 3, 2025, at 8:00 pm, the Old Town School of Folk Music will host a free concert series, World Music Wednesdays, featuring musicians from all around the world. Culture and countries represented … [Read more...] about Free World Music Wednesday Concerts
Hyde Park Handmade Artisan Bazaar
For ten years, the free Hyde Park Handmade Artisan Bazaar has supplied a monthly pop-up of hand-crafted goodies beloved by loyal customers. Don't miss the fun at the 2025 fall and winter dates on September 21, October 19, November 23 and December 21. This eclectic indoor … [Read more...] about Hyde Park Handmade Artisan Bazaar
Chi-Village Kwanzaa Celebration
The exuberant seven-day African American tradition of Kwanzaa will be celebrated with eight hours of free music, dance, workshops and presentations by Chi-Village in the Roseland community on December 26, 2024. The second annual Chi-Village Kwanzaa Celebration weaves the past and … [Read more...] about Chi-Village Kwanzaa Celebration
Millennium Park Holiday Sing-Alongs
Celebrate the season with festive live concerts every Friday with the Millennium Park Holiday Sing-Along starting on December 6, 13 and 20, 2024. Join a diverse group of choirs and ensembles as they light up the park with music. The holiday Sing-Along kicks off on Fridays from 6-7 … [Read more...] about Millennium Park Holiday Sing-Alongs
Earlybird Discount Tickets at Holidaze Lincoln Park Zoo
Stroll around Lincoln Park Zoo under the glow of millions of lights while enjoying a live DJ during the annual Adults Night Out event, Holidaze, on December 12, 2024. Feel jolly as you dive into the spirit of the season with live ice carvings, pop-up bars and food carts, free rides on the … [Read more...] about Earlybird Discount Tickets at Holidaze Lincoln Park Zoo
Free Time Out Market Fifth Anniversary Party
Join the all-day celebration for five years of food, drinks and events during the Fifth Anniversary Celebration of Time Out Market, on November 16, 2024. Enjoy food and drink specials and live DJs in the West Loop neighborhood. Head to Time Out Market for festivities filled … [Read more...] about Free Time Out Market Fifth Anniversary Party
