How to Go All Out for Halloween in Chicago
Halloween is less than two weeks away, and Chicago has plenty of opportunities to celebrate. From pumpkin carvings, to costume parties, to the classic trick-or-treating, you’d have to try hard not to find something to do on All Hallows' Eve. Host Jacoby Cochran breaks down the best activities this year with Jenny LeFlore, aka Mama Fresh. They discuss what makes the perfect spooky itinerary and the events they’re most excited to go to. Plus, the best Chicago-themed costumes you can try.
Arts in the Dark Halloween Parade on State street - October 21
The Rink - October 30 for local daycares
Jack’s Pumpkin Pop Up - September 21 - November 5
Frankenstein’s Mad Scientist Cocktail Lab
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