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
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Free Movies at Gallagher Way
Enjoy the fun of viewing movies al fresco during the Gallagher Way Outdoor Movie Series. The screenings will feature the spooky season theme on October 15 and 22, 2025. The line-up of family-friendly films includes "Hocus Pocus," the classic wacky witches film with Bette … [Read more...] about Free Movies at Gallagher Way
Chicago Halloween Cruises from $30
Celebrate the spooky season with a fun-filled cruise along Lake Michigan that combines costumes, dancing and drinks with views of the iconic Chicago skyline. 312 Cruises offers cruises as cheap as $30 on October 25 and 31, and November 1, 2025. Hop aboard a three-story, 140-foot luxury … [Read more...] about Chicago Halloween Cruises from $30
Adults Night Out Howl-o-ween at Lincoln Park Zoo
Get ready for spooky animal shenanigans at Adults Night Out Howl-o-ween at Lincoln Park Zoo. Visitors 18 and over can stroll the zoo after dark, sip cocktails and have a fang-tastic time on October 24, 2025. Pop-up bars, corn hole, Jenga and free rides on the AT&T Endangered Species … [Read more...] about Adults Night Out Howl-o-ween at Lincoln Park Zoo
Ravenswood Costume Crawl
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
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
