Halloween in Chicago isn’t just about costumes and candy, it’s a full-on celebration of spooky thrills, vibrant traditions, and unforgettable experiences. From haunted river cruises that uncover the city’s ghostly past to masquerade balls brimming with glamour and mystery, this season offers something for everyone. Whether you’re looking for family-friendly fun, a festive brunch, or a night of eerie excitement, Heron Agency’s guide has you covered with the best events and activities to make this Halloween one to remember.
Carnivale’s Masquerade Ball
Carnivale will celebrate Halloween weekend with two signature events. On Friday, October 31 at 7 PM, the Masquerade Ball returns with signature dishes, a premium open bar, live DJ and dancing, aerialists, specialty performances, and face painters. The festivities continue on Sunday, November 2 at 11 AM with a Día de los Muertos Brunch, featuring a festive buffet, live Catrina characters, face painting, roaming performers, photo moments, and themed cocktails and mocktails.
City Cruises’ Seadog Haunted Tours
Step aboard City Cruises’ Seadog Haunted Tours for a fun-filled journey through Chicago’s history of ghosts, spirits, scandals, and sins. As guests cruise along the Chicago River, expert docents weave a delightful touch of humor into the exploration of the Windy City’s darker side. Passengers are enchanted by tales of supernatural occurrences and infamous figures, all while enjoying the stunning views of Chicago’s architectural skyline. This haunted cruise is also BYOB, and pups cruise free, making this spooktacular adventure perfect for everyone!
Roseland Community Hospital’s 5th Annual Trunk or Treat
Roseland Community Hospital is keeping the community safe this Halloween by offering an alternative to traditional trick-or-treating by featuring decorated cars on display providing treats to families of all ages during their 5th Annual Trunk or Treat event on Friday, October 31, 2025, from 4-6pm. The Roseland Community Hospital’s Trunk or Treat event is meant to provide a safe alternative to the Halloween tradition. Treats, games, and a live DJ will be onsite to entertain families and children of all ages. Additionally, there will be special highlights and educational information about breast cancer available for attendees.
