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
family friendly
Free Slightly Spooky October at Navy Pier
Spend the spooky season watching movies, creating fun projects and trick-or-treating at Navy Pier. Enjoy interactive art and performances during Slightly Spooky October at Navy Pier on Saturdays throughout the month on October 17, 24 and 31, 2026. Dive into fun and watch movies like … [Read more...] about Free Slightly Spooky October at Navy Pier
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
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
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
Jack’s Pumpkin Pop Up
Wander through pumpkin patches and corn mazes while you enjoy the season at Chicago's largest fall festival, Jack's Pumpkin Pop Up, located near Goose Island, from September 19 to November 1, 2026. The large number of all-ages festivities make Jack's one of the most popular fall excursions. … [Read more...] about Jack’s Pumpkin Pop Up
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
First Lady Fall Cruises
One of Chicago's most iconic experiences is sailing on the scenic Chicago Architecture Center (CAC) River Cruise aboard First Lady and absorbing the city's stunning skyline while learning about its design history. The fun continues through the fall, with cruises floating along the shore … [Read more...] about First Lady Fall Cruises
Destinos Chicago Latino Theater Festival
Celebrate Hispanic Heritage Month along with Latino theater and dramatic creativity at the ninth annual Destinos: Chicago International Latino Theater Festival for three weeks from September 14 to October 11, 2026, at theaters across the city. The Chicago Latino Theater Alliance … [Read more...] about Destinos Chicago Latino Theater Festival
St. Benedict’s Oktoberfest
Get ready for the welcoming traditional German toasts of "Prost!" to echo throughout the courtyard during the 60th annual St. Benedict Oktoberfest on October 2-4, 2026. St. Benedict parish celebrates its German roots with a family-friendly fest that includes German food and … [Read more...] about St. Benedict’s Oktoberfest
Ravenswood ArtWalk
The Ravenswood Corridor community celebrates 24 years of the annual Ravenswood ArtWalk on September 12-13, 2026. The area's artists, manufacturers and brewers will welcome visitors during the ArtWalk with a host of fun and interactive activities. Unfolding from Lawrence to Irving Park St.. … [Read more...] about Ravenswood ArtWalk
