October isn’t just about scary monsters, haunted houses and candy everywhere. It’s also about being treated to lots of sweet savings and discounts. And, for frugal families, it’s always a big treat whenever they can save money — especially because the winter holidays are just around the … [Read more...] about Halloween deals, discounts and freebies 2025
Expired
Chicago Free and Cheap Halloween Events
Whether you like parades, tours, parties or old school trick or treating, there are lots of free and cheap Halloween events to explore all over Chicago. Check out everything from boat rides to shopping and fall fests in our roundup below. Chicago Halloween Cruises Float along … [Read more...] about Chicago Free and Cheap Halloween Events
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 25- 26, 2025, 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
Free Chicago Hauntings Night Tour Walk
Listen to creepy stories, walk around spooky downtown landmarks and discover Chicago's eerie past with the free Hauntings Chicago Night Tour with Chicago Walking Tours on October 31, 2025. Follow the trail of the most haunted spots in Chicago with this guided two-hour tour. Learn … [Read more...] about Free Chicago Hauntings Night Tour Walk
Free Meet Me on Milwaukee
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
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
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
Free National Museum of Mexican Art Dia de los Muertos Chicago
Celebrate the Mexican tradition of Dia de los Muertos or Day of the Dead with the free "Dia de Los Muertos Xicago" event organized by the National Museum of Mexican Art on October 25, 2025, 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
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
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
