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The Classiest Way To Celebrate Halloween In Chicago

With Halloween right around the corner, there are tons of events to check out near the Gold Coast. However, a masquerade is the only surefire way to make your celebration a classy one. Here’s a list of Halloween masquerades for October 2019.


Masquerade Ball at the Drake 2019

Fri, Oct 25, 8:00 PM – Sat, Oct 26, 12:30 AM

After checking into Walton Residence, check out the Masquerade Ball at the Drake Hotel. Located in the Gold Coast off Walton Street, this hotel has one of the most gorgeous ballrooms in Chicago. This night will feature live music from the band Sway, who will play everything from Motown, to swing, to top 40.

The Drake, a Hilton Hotel
140 East Walton Place
Chicago, IL 60611
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Titanic Masquerade – Pier Pressure Chicago Halloween Yacht Party

Fri, Oct 25, 11 PM – Sat, Oct 26, 2 AM

Lose yourself in the beautiful, yet tragic scenery of the Titanic. This magnificent cruise will take you back in time with a replica of the doomed ship filled with over 600 party people raised from the dead. The Spirit of Chicago has four decks occupied by 2 separate DJs and dance floors.

Spirit of Chicago
600 E. Grand Ave.
Chicago, IL 60611
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Vanity Affair | Vampire Masquerade Ball

Wed, Oct 30, 7 – 9 PM

Nothing says Halloween like vampires and nothing says extravagant like drag queens. Miss Toto, Discord Addams, Gidget Von Addams, and Claire Vovyant have put together a fierce night for members of the LGBTQ community and its allies to gather, drink, and have a ball. Join them Wednesday night at the W Chicago – City Center.

W Chicago – City Center
172 West Adams Street
Chicago, IL 60603
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