Spooky Halloween Events in Chicago
It’s almost time to don your most creative Halloween costumes, hit the dance floors, and trek around town to embrace this most spooktacular season and all of its glorious events. And, here in Chicago, we celebrate all things Halloween all month long! Never mind all of those witches, vampires, spider webs and walking dead out there – the scariest thing you’ll experience this Halloween is just how many decisions you’ll have to make about how you’re going to spend it! With so many exciting events going on in and around town, you really can’t go wrong. But, if you want a little advice on where to start looking for all of the fun, here’s a look at some of the events we’re most looking forward to this Halloween:
Jack’s Pumpkin Pop-up
When: Through November 3rd
Where: River West/West Town
If you’re looking for that classic tradition of running through a corn maze but don’t want to make a trip out to the suburbs, check out Jack’s Pumpkin Pop-up. This new Halloween-themed experience brings seasonal outdoor fun to a two-acre lot near Goose Island. Explorers can also enjoy carnival games, nightly live performances, and pumpkin carving all while sipping seasonal beer and cider.
Arts in the Dark
When: October 20th
Where: The Loop
The Arts in the Dark parade celebrates the Halloween season by flooding the streets of Chicago with floats, performers, puppets, and lanterns. And, it really is a site to see, as most of the costumes and featured parade objects are made by local artists showing off some of their most creative and spooky works. This year’s parade will span from Grant Park to State Street, beginning at Lake Street moving south to Van Buren.
Nocturna All Hallow’s Eve Ball
When: October 26th – 27th
Where: Wrigleyville
For those looking to let their inner goth out, head to the Nocturna All Hallow’s Eve Ball. The annual event will feature DJ Scary Lady Sarah spinning some dark tunes to set the perfect energetically spooky mood while guests enjoy all sorts of fun, including a photobooth, a pin the skull on the skeleton game, a balloon artist, and more creepy surprises.
Drake Hotel Masquerade Ball
When: October 27th
Where: Streeterville
Get lost in a sea of masked, costumed guests at the historic Drake Hotel’s Masquerade Ball. Attendees are encouraged to show up in black tie attire with masks on to enjoy a night of live music from the Flat Cats, drinks, dancing, and more.
Lyric Halloween Masquerade
When: October 27th
Where: The Loop
The Civic Opera House is also hosting a masked ball this season. The Lyric Halloween Masquerade is an event that raises money to support emerging operatic talent. All guests are encouraged to arrive in formal attire and masks ready to enjoy a night of cocktails, music, treats, and more!
Underworld’s Fair
When: October 27th
Where: The Loop
Take your spooky, surreal Halloween experience to a whole new level at the Underworld’s Fair! The annual party hosted by the Chicago Athletic Association brings to life a terrifying scenario where an ecological disaster has taken place and caused Cook County to declare a state of dystopia. Guests must take refuge in Stagg Court where DJ Pierre will be spinning a soundtrack to keep survivors going all night. Then, when the dance floor is cleared at midnight, the party will head to the Game Room for more thrilling fun.
Haunted Halloween Ball
When: October 27th – 28th
Where: Downtown
The Haunted Halloween Ball will take over the Congress Plaza Hotel for a celebration of dancing, spooky costumes, and fun. The hotel’s ballrooms will be transformed into haunted spaces for the evening, featuring go-go dancers, a vampire bellmen prowling through party guests, and zombie cocktail servers. There will also be a live DJ, a costume contest and gorgeous views of the Chicago skyline.
Haunted Rooftop at Cerise
When: October 27th – 28th
Where: The Loop
This spooky late-night bash is one you won’t want to miss! The party will take over the 25th and 26th floors of the Virgin Hotels Chicago, where guests will find two dance floors, drinks and stunning skyline views.
Embrace this exciting time of year, and mark your calendars with these spooky events happening all month long. We’ll see you out there for a frightfully good time!
