Chicago’s Largest Halloween Festival
Something wicked this way comes! My favorite annual Chicago pop-up event is back. Jack’s Pumpkin Pop-Up, Chicago’s largest Halloween festival, is 2 acres of festive photo ops, carnival games, a corn maze, cocktail bars, axe throwing, food, and pumpkins for sale. It’s open all October and is perfect for feeling all the fall vibes. I have greatly enjoyed this annual pop-up (view pictures from my 2022 and 2021 recaps). Read below for this year’s experience!
Jack’s Pumpkin Pop-Up Photo Ops
My favorite part about Jack’s Pumpkin Pop-Up, and the reason we’re eager to go back each year, is all the great photo ops! The unique fall and Halloween backdrops are the perfect urban opportunity to get into the spooky spirit. Each year they have oldie-but-goodie photo ops (like the pumpkin house) as well as new ones (like the window from the TV show Wednesday). The window,
Jack’s Pumpkin Pop-Up Food & Drink
Jack’s Pumpkin Pop-Up offers multiple cocktail bars and food for purchase. There is a taco truck, sweets from Eiffel Waffle, and other food – including apple cider donuts, cheeseburgers, hot dogs, elote, BBQ chicken sandwiches, and jumbo pretzels. The bars offer both alcohol and nonalcoholic options. We tried the apple cider (cold) and loved it! Make sure to bring a credit card as they do not accept cash. Beer, liquor, and ciders range between $9-$14.
Specialty Cocktails
- Jack’s Potion of the Day – Specialty cocktail of the day
- Jack’s Midnight Moonshine – Batched in-house with a hint of cranberry & peach
- Fall in Love – Whipped vodka, cardamom & cranberry
Jack’s Pumpkin Pop-Up Tickets
Jack’s Pumpkin Pop-Up will be open to the public now through October 31, 2022. Tickets start at $22, and $20 for kids 5-11 years old. Add-ons include drink tickets, orange pumpkins, apple cider donuts, carnival games, axe throwing, and gemstone mining. Tickets are offered for time slots throughout the day and evening and can be reserved online in advance. Have a fun, spooky time!
