10 Halloween-themed date nights in Chicago

The dark, spooky atmosphere of Halloween provides the perfect setting for a romantic date, and Chicago has just about any adults-only event under the full moon for you and your boo. So book a sitter and spice up your traditional date night with a Halloween twist.

The Nightmare Before Halloween: A Tim Burton Experience

When: Oct. 17-31

Where: Headquarters Beercade, 213 W. Institute Place, Chicago

Cost: Free admission

Explore a magical, sinister world inspired by Tim Burton as Headquarters Beercade in Lincoln Park creeps into town. Enjoy themed cocktails, live entertainment, trivia and installations inspired by some of Tim Burton’s finest: Sweeney Todd, Edward Scissor Hands, Beetlejuice, and more.

IT Halloween Pop Up

When: Oct. 11-Nov.1

Where: Replay Lincoln Park, 2833 N. Sheffield Ave., Chicago

Cost: Free admission

Scary movies are a great excuse to cuddle with your person, and if the two of you visit the IT Halloween Pop Up at Replay Lincoln Park, we have a feeling you’ll get very cozy. Brave your fears and check out terrifying IT art installations based on the books and movies while you sip on IT handcrafted cocktails, including the Black Widow Smash, the S.S. Georgie and the Pennywise Punch.

Adults Night Out: The Great Pumpkin Glow

When: Oct. 24, 6:30–10 p.m.

Where: Lincoln Park Zoo, 2001 N. Clark Street, Chicago

This rare, adults-only evening at the Lincoln Park Zoo features Bat and Spider Chats, where patrons can get up close and personal with these creepy species and their handlers. There’s also a Haunted Trail Walk, Corn Maze and a special screening of Goosebumps on the South Lawn to enhance the Halloween mood.

Dawn of the Dead Yoga

When: Oct. 26, 9-10 a.m.

Where: 360 Chicago Observation Deck, 875 N. Michigan Ave., Chicago

Cost: $18 (includes a general admission ticket to the Observation Deck)

While not necessarily a date night, if you’re lucky enough to send the kids to a sleepover with grandma the night before, kick start your weekend by rising and shining early for Chicago’s most haunted yoga sesh. Stick around after to sip on a signature pumpkin spice mimosa from Bar 94. 

Halloween Masquerade

When: Oct. 26, 8 p.m.-midnight

Where: Lyric Opera House, 20 N. Wacker Drive, Chicago

Cost: $150 (includes open bar, hors d’oeuvres, and access to the After Party at Public House)

Often referred to as the city’s most glamorous Halloween party, the breathtaking opera house will be decked out in sophisticated Halloween decor, as guests enjoy drinks from local breweries and distilleries while dancing to beats spun by DJ Metro. Come dressed to impress in a costume and mask for this lavish affair that directly supports the emerging operatic talent of The Patrick G. and Shirley W. Ryan Opera Center. 

Haunted Halloween Ball

When: Oct. 26, 9 p.m.

Where: Congress Plaza Hotel, 520 S. Michigan Ave., Chicago

Cost: $20 and up

Named one of the 13 most haunted hotels in the world due to reported paranormal activity and ghostly sightings, it’s only fitting that Chicago’s annual Haunted Halloween Ball be held at the Congress Hotel. This VIP event combines the exclusiveness of a luxury hotel gala, the terror and chills of a haunted house and the traditional scares of Halloween, with appearances by vampire bellmen, zombie cocktail servers and theatrical performances by costumed go-go dancers.

Crawl-O-Ween

When: Oct. 26, 6-10 p.m.

Where: Parkway Bank Park Entertainment District, 5501 Park Place, Rosemont

Cost: $10 (includes access to the bar crawl, two Zanies Comedy Club tickets and drink specials at each location).

The true adult version of trick-or-treating, make your way to seven bars in four hours during Parkway Bank Park’s annual grown-up Halloween event! Stops include Adobe Gilas, Bub City, Five Roses, Hofbrauhaus Chicago, Kings Dining & Entertainment, Park Tavern, and Sugar Factory.

Hocus Pocus Halloween Trivia

When: Oct. 30, 7:30 p.m.

Where: D.S. Tequilla Company, 3552 N. Halsted St., Chicago

Cost: Free

Whether you sing along to Bette Midler’s “I Put a Spell on You” every Halloween, or recently fell in love with the Sanderson sisters during a TV marathon, the second annual Hocus Pocus Trivia at D.S. Tequila Company in Wrigleyville is one event you won’t want to miss. Put your knowledge about these witches to the test, as questions will include storyline, actors, plot, history of the movie and more. Plus, $300 in prizes is up for grabs.

Pier Pumpkin Lights

When: Through Nov. 2

Where: Navy Pier, 600 E. Grand Ave., Chicago

Cost: Free

Rekindle the romance beneath nearly 1,000 twinkling pumpkins on display at Pier Pumpkin Lights, Navy Pier’s first-ever Halloween pop-up experience. Explore six installations of lights, displayed across the 50-acre Pier, stretching from the main entrance to the iconic wheel. Best experienced after dusk, featured stations which include everything from Pumpkin Picasso to Garden of Totems are perfect for snapping selfies.

Jack’s Pumpkin Pop Up

When: Through Nov. 3

Where: 1465 N. Elston Ave, Chicago

Cost: $19 and up

If you can’t decide on a date night spot, Jack’s Pumpkin Pop Up is the ultimate tie-breaker, featuring everything from the city’s largest corn maze (with a hidden bar) to axe throwing stations and carnival games. Located on a full two acres in Goose Island, this multi-sensory adventure also packs plenty of no filter needed Instagrammable photo opps.


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