7 Spooktacular Ways to Spend Halloween in Chicago

Charli Renken Charli Renken

7 Spooktacular Ways to Spend Halloween in Chicago

Halloween is just around the corner, ChiTown. Here’s a list of the best events to get you in the ghostly mood.

It finally feels like fall in Chicago and with Oct 31 getting closer, it’s time you nailed down your Halloween plans. Chicago has tons of events to choose from for an eerie good time and lucky for you, we’ve narrowed it down to seven perfect ways to celebrate All Hallow’s Eve. [Feature photo: Shutterstock]

1. Start with an awesome costume!

Photo: @wolfmims

Where: Fantasy Costumes, 4065 N. Milwaukee Ave Chicago, IL

Regular Hours: Mon-Sat: 9:30 a.m. – 8 p.m., Sun: 11 a.m. – 5 p.m. 

Halloween hours: Oct 24-Oct: 31 24/7

You can’t get spooky without a terrifying costume to match! If you’re still scrambling to find the perfect Halloween attire, Fantasy Costumes has your back. With 18,000 square feet of ghostly attire to choose from, you’ll have no trouble finding something to make your best ghoul-friends scream. Best of all, Fantasy Costumes is open 24 hours Oct 24-Oct 31, so even if you work the graveyard shift, you’ll still have time to score a great costume. 

2. Watch a spooky movie.

Where: Any Chicago AMC Theatre

Cost: $10.99

Oct is filled with tons of fearsome flicks to get your in the mood for Halloween. Curl up with your boo at AMC’s showings of terrifying titles like Maleficent: Mistress of Evil, Joker, The Addams Family, It: Chapter Two or Scary Stories to Tell in the Dark. Grab some popcorn and candy with a pop to wash everything down and scare yourself silly. 

Get discount tickets to AMC movies here.


3. Take the perfect Halloween Instagram Pic at this corn maze pop-up.

Photo: @thatpolishchick

Where: Jack’s Pumpkin Pop-Up, 1465 N Elston Ave, Chicago, IL 60642

When: Now through Nov 3. 

Mon-Fri: 4pm-10pm 

Weekends: 11 a.m. – 10 p.m.

Cost: Tickets start at $25

You’ve got the perfect costume and watched a scary movie to get you in the mood. Now it’s time to document the festivities with the perfect Halloween Instagram shot. Head to Goose Island for Jack’s Pumpkin Pop-Up, a corn maze pop-up with a hidden bar and sparkling photo ops. Make it through the corn maze and reward yourself with a hard cider or Tito’s cocktail. The pop-up also hosts several special events such as “Fall Cider Fest,” “Haunted Corn Maze,” an Oktoberfest event and many more!  

4. Take a ride on a Haunted Ghost Ship.

Where:  Spirit of Chicago Yacht, 600 East Grand Ave, Navy Pier, 60611

When: Thurs, October 31. Boat boards at 6 p.m., departs at 6:30 p.m., and returns at approximately 8:30 p.m.

Cost: $30

Ready for some late-night haunts? Step aboard the Spirit of Chicago Yacht which is haunted by the spirit of a wild party animal! Dance to an awesome DJ in your Halloween best, enjoy delicious drinks, and take in beautiful sights of the city at this incredible Halloween bash. With three climate-controlled interior decks and a stylish sky deck, there’s nowhere better to celebrate than on the water.

Buy tickets here. 


5. Go adult trick-or-treating.

Where: Concrete Cowboy, 646 N Franklin St, 60654

When: Sat, October 26 at 4 p.m. – 2 a.m.

Thursday, October 31 at 6 p.m. – 2 a.m.

Cost: $10

Just because you’re an “adult” now doesn’t mean you can’t dress up and hunt around Chicago for free candy. Trick or Drink is a Halloween bar crawl that allows you to relive your Halloween childhood memories while enjoying delicious alcoholic drinks. You’ll receive a wristband that gets you into all participating bars and clubs and enjoy a discount special drink menu.  This is the best way to party at some of the best clubs in Chicago for cheap. Don’t miss it!

Buy tickets here.


6. Dance with the Devil at the Poetry Brothel

Where: The Den Theatre, 1331 North Milwaukee Avenue, 60622

When: Sun Oct 27 at 7 p.m. – 11 p.m.

Cost: $40

If haunted theatre is more your speed, The Poetry Brothel invites you to discover if you’re a saint or sinner in this magical performance. All Saints & All Sinners features poetry readings, live music, burlesque, vaudevillian comedy, and immersive games of chance, fate, fortune and more! Enjoy a delectable night of shenanigans and debauchery. The veil between worlds may be thin during Halloween, but at The Poetry Brothel, the antics are thicc!

Buy tickets here.


7. Attend the Halloween Ball at Navy Pier.

Photo: Shutterstock

Where: Aon Grand Ballroom, 600 East Grand Ave, Navy Pier, 60611

When: Sat Oct 26 at 8 p.m. – 1 a.m.

Cost: $35

Get your ghouly groove on early at Nightmare on Navy Pier’s Halloween Ball. The Aon Grand Ballroom is haunted once again and the only way to banish these spirits is to party the night away. Enjoy a cash bar, multiple DJs, and a lively dance party during Halloween weekend. Grab a costume (or don’t, we don’t judge) and head over to Navy Pier. This is one of the most anticipated parties of the year, so don’t miss it!

Buy tickets here.


For more Halloween events, check out our full list of frightening activities here. 

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