Dive into the joy of the season with a visit to the Ravenswood Costume Crawl, filled with Halloween-themed fun, seasonal goods, treats and drinks on October 29, 2025. This thrill-filled event will transform Ravenswood's Montrose Avenue of shops and restaurants into a spooky space for sipping, … [Read more...] about Ravenswood Costume Crawl
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Super Horror Rama Film Fest
Dive into the creepiness of the scary season with two nights of obscure horror films at Super-Horror-Rama Film Fest on October 10-11, 20245 in the Lakeview neighborhood at the Music Box Theatre. Prepare to have petrified fun with a showcase of horror film oddities with the theme of … [Read more...] about Super Horror Rama Film Fest
Free Slightly Spooky Saturday at Navy Pier
Spend Halloween trick or treating at Navy Pier and enjoy interactive art and performances during Slightly Spooky Saturday at Navy Pier on October 25, 2025. Put on your costume and stop by 30 indoor candy stations during this all-day, free event. Besides sweet treats, look out for aerial … [Read more...] about Free Slightly Spooky Saturday at Navy Pier
Haunted Halsted Halloween Parade
The ultimate Chicago Halloween celebration kicks off with the 26th Annual Haunted Halsted Halloween Parade and costume contest on October 31, 2025. Throw together your most creative, witty costume for the dramatic spectacle of the Haunted Halsted Halloween Parade. Prepare to see … [Read more...] about Haunted Halsted Halloween Parade
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
Open House Chicago
Explore the architectural and cultural treasures that Chicago is famous for during the annual Open House Chicago events. Visit over 170 sites in more than 20 neighborhoods across the city during the in-person activities on October 18-19, 2025. Go behind the scenes in members-only clubs, … [Read more...] about Open House Chicago
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
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 15th annual West Town Art Walk on October 3-5, 2005. The West Town neighborhood bubbles with color, food and art in all forms during this popular … [Read more...] about West Town Art Walk
Taste of Northalsted
Stroll down the bustling North Halsted strip and sample an assortment of food and drinks during the Taste of Northalsted on October 4, 2025, in the Lakeview neighborhood. Wander through Northalsted during autumn and indulge in a culinary adventure with the Fall Taste of Northalsted! Featuring … [Read more...] about Taste of Northalsted
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 9-19, 2025. Runway shows, activations, exhibits and events will highlight Chicago's design and fashion history in neighborhoods across the city. The … [Read more...] about Chicago Fashion Week
Free Lincoln Park Spooky Zoo
Celebrate the scary season with a visit to Lincoln Park Zoo for trick or treating among the animals at the annual Spooky Zoo event on October 18, 2025. Stroll around the zoo and collect treats while supplies last. Kids can also enjoy interactive storytelling and live music on the Main Mall … [Read more...] about Free Lincoln Park Spooky Zoo
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 10-19, 2025. 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
