Go pumpkin hunting, dance to live music, create arts and crafts and enjoy the season at Gallagher Way's annual Pumpkin Party on October 24, 2026, 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
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Free Loop Arts Fest
Head to State Street, that great street, to participate in free art activations, live music, dance, theater and fashion shows at the Loop Arts Fest on October 17, 2026. Sample local food and art vendors as you roam down State for three blocks of art and creativity. The streets on State … [Read more...] about Free Loop Arts Fest
Free National Museum of Mexican Art Dia de los Muertos Chicago
Celebrate the Mexican tradition of Día de los Muertos or Day of the Dead, with the free "Día de Los Muertos Xicago" event organized by the National Museum of Mexican Art on October 24, 2026, in the Pilsen community. Honoring loved ones who have passed away with ofrendas or altars filled with … [Read more...] about Free National Museum of Mexican Art Dia de los Muertos Chicago
Free Festival del Arte Popular at National Museum of Mexican Art
Start your holiday shopping early by checking out the masterful work of Mexican artisans at the annual Festival del Arte Popular at the National Museum of Mexican Art on October 13-18, 2026. Witness live demonstrations of intricate Mexican folk art and meet artists from all over Mexico at … [Read more...] about Free Festival del Arte Popular at National Museum of Mexican Art
Chicago Fashion Week
The cultural and stylistic diversity of the Windy City will take the stage with the return of Chicago Fashion Week, from October 8-18, 2026. Runway shows, activations, exhibits and events will highlight Chicago's design and fashion history in neighborhoods across the city. The thrilling … [Read more...] about Chicago Fashion Week
Open House Chicago
Explore the architectural and cultural treasures that Chicago is famous for during the annual Open House Chicago events. Visit over 200 sites in more than 20 neighborhoods across the city during the in-person activities on October 17-18, 2026. Go behind the scenes in members-only clubs, … [Read more...] about Open House Chicago
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 24, 2026, 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
West Town Art Walk
Enjoy visual art, music, and fashion while browsing restaurants and shops along Chicago Avenue in the bustling West Town neighborhood during the 16th annual West Town Art Walk on October 2-4, 2026. The West Town neighborhood bubbles with color, food and art in all forms during this popular … [Read more...] about West Town Art Walk
Reeling International Film Fest
The second-oldest LBTGQ+ film festival in the country kicks off with an exciting line-up of international features, documentaries and shorts with the 44th annual Reeling International Film Festival on September 17-27, 2026. The rich diversity of the queer community is showcased during the … [Read more...] about Reeling International Film Fest
Chicago Fall Market for Makers
Celebrate the work of independent artists and makers specializing in home decor, fashion, art, design, food and more at the Chicago Fall Market for Makers on October 24- 25, 2026, in the Ravenswood neighborhood. Score one-of-a-kind deals and support small businesses at this market, which … [Read more...] about Chicago Fall Market for Makers
Oktoberfestiversary
Dovetail Brewery and Begyle Brewing serve up their annual fall street festival with Oktoberfestiversary on October 10-11, 2026, in the Ravenswood neighborhood. Enjoy brews, live music and food in the spirit of the season. Sip on special tapings from Beglye and Dovetail while munching on … [Read more...] about Oktoberfestiversary
Lincoln Square Ravenswood Apple Fest
Enjoy Fall fun with apple-inspired food, drinks and artisan goods at the beloved Lincoln Square Ravenswood Apple Fest, October 2-4, 2026. 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 … [Read more...] about Lincoln Square Ravenswood Apple Fest
