Halloween Costume Contests in Chicago 2025

Explore The Best Of Pumpkin Costume Parties & Events in Chicago

Haunted Hotel Halloween Ball 2026 at Congress Plaza Hotel

 Congress Plaza Hotel Chicago 31 Oct 2026
USD 30 TO 1,166

Chicago Halloween Party Cruise | Pier Pressure® Black Pearl

 Spirit of Chicago Yacht 31 Oct 2026
USD 23 TO 56

Chicago Halloween Bar Crawl 2026

 PB&J: Pizza Beer and Jukebox 31 Oct 2026
USD 10 TO 46

The Official Halloween Bar Crawl - Chicago

 Black Hole Bar 31 Oct 2026
USD 17 TO 86

Afrobeats Saturdayz: Halloween costume party (Up to $1000 in prizes)

 Masada 31 Oct 2026
USD 0 TO 176

Afrobeats Fridayz @ Masada: Halloween Costume party (Up to $1000 in prizes)

 Masada 30 Oct 2026
USD 0 TO 176

Ivy+ Alumni Chicago Halloween Costume Party - In Person!

 The Sterling Food Hall 29 Oct 2026
FREE

1st Annual Nightmare In The Summer Halloween Costume Party

 Sal’s On Tap(Old Park Tavern) 19 Jul 2026
USD 23

Haunted Halloween Night Lake Cruise on Friday, October 30th

 Anita Dee II Boarding at Dusable Harbor (See map and directions at bottom of page for exact location) 30 Oct 2026
USD 20 TO 42

Costume Drive for our Upcoming Annual BOOOtique

 Portage Park Farmers Market 20 Sep 2026
FREE

PHANTASIA Fashion Show

 The Augusta Loft 15 Oct 2026
USD 23 TO 55

How to Store Costumes

 Idea Box Integrated Arts 22 Aug 2026
USD 23