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 29 TO 57

Chicago Halloween Bar Crawl 2026

 PB&J: Pizza Beer and Jukebox 31 Oct 2026
USD 24 TO 31

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

THE SIGNING OF THE DECLARATION OF INDEPENDENCE PARTY

 Parlay Lincoln Park 3 Jul 2026
USD 10

THE SUMMER HALLOWEEN COSTUME PARTY

 SAL'S ON TAP ( OLD PARK TAVERN) 19 Jul 2026
USD 23

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

PHANTASIA Fashion Show

 The Augusta Loft 15 Oct 2026
USD 20 TO 50

Costume Drive for our Upcoming Annual BOOOtique

 Portage Park Farmers Market 20 Sep 2026
FREE