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jacks' pumpkin pop up

Jack’s Pumpkin Pop-Up 2023

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!

Jack’s Pumpkin Pop-Up 2022

Jack’s Pumpkin Pop-Up

My favorite pop-up is back this fall! Jack’s Pumpkin Pop-Up is 2 acres of festive photo ops, carnival games, a large corn maze, bars, axe throwing, gemstone mining, and pumpkins for sale. Open now through October 31, the pop-up’s Insta-worthy backdrops are a can’t-miss experience! I’ve enjoyed the annual event very much. View my favorites from this year below!

Jack’s Pumpkin Pop-Up Photo Ops

The best part about Jack’s Pumpkin Pop-Up are all the great photo ops! They really can’t be beat if you’re looking for unique fall and Halloween backdrops. There’s so many different options! Each year has an ode to Jack Skeleton, a pumpkin house, and a variety of spooky aesthetic. My favorites this year included a Jack’s Pumpkin barn house, Hocus Pocus with Winafred’s spell book, “Happy Fall Y’all” with a colorful leaf umbrella, an annual height meter, and a sugar skull display found in the middle of the pop-up’s corn maze.

Jack’s Pumpkin Pop-Up Food & Drink

This Goose Island event offers multiple bars and a food truck for purchase. When we went it was a taco truck. The bars offer both alcohol and nonalcoholic drink options. We tried the apple cider (cold) and loved it! Jack’s Pumpkin Pop-Up is credit card only and does not accept cash. Beers and ciders range between $9-$11 with specialty cocktails priced at $14.

Specialty Cocktails

  • Fall in Love – Spellbinding potion of Whipped Vodka, Cardamon & Cranberry
  • Jack’s Midnight Moonshine – Batched in-house with a hint of Cranberry & Peach
  • Hocus Pocus – Magical concoction of Vodka infused with Fireball, Fig & Peach

Jack’s Pumpkin Pop-Up Tickets

Jack’s Pumpkin Pop-Up will be open to the public now through October 31, 2022. General admission starts 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.

Jack’s Pumpkin Pop-Up 2021

My favorite seasonal pop-up is back! Jack’s Pumpkin Pop-Up features Insta-worthy photo opps and a corn maze, as well as food & drink, carnival-style games, axe throwing and pumpkins for an additional cost. This year I attended with my sister, and we got to enjoy some of those add-ons. Read below to learn more about our experience!

Jack’s Pumpkin Pop-Up Photo Opps

This 2-arce pop-up is open now through October 31, 2021 in Goose Island. The best part about the event, in my opinion, are the photo opps. They have so many! Some are fall themed, while others deal more with pop culture. My favorite spots were the pumpkin house featured at the entrance of the pop-up (shown above), the fortune teller’s crystal ball, a black and white angel mural, a pink #freebritney cage, and Winafred’s spell book from Hocus Pocus. There were also some odes to Jack Skeleton, autumn, coffins, and more.

Jack’s Pumpkin Pop-Up Food & Drink

Aside from your usual water and soda, food and alcohol are offered at this pop-up. We ordered a cheeseburger and hot dog. My sister was pleasantly surprised to see that the cheeseburger came on a pretzel bun! The hot dog was pretty good, too. Also on the menu were walking tacos, grilled corn on the cob, elote, hot pretzels, nachos & cheese, Cheetos with cheese, and apple cider donuts. The donuts were delicious! Full bars are offered for those 21+ and up.

My Fall-Inspired Outfit

Although I’m not a fan of colder weather, I do love fall clothing. I was extremely excited to have the chance to wear my latest purchase, featured in my pictures taken at Jack’s Pumpkin Pop-Up. I’ve linked the items here for your viewing!

Tickets to Jack’s Pumpkin Pop-Up

Jack’s Pumpkin Pop-Up will be open to the public now through October 31, 2021. General admission costs $25, and $23 for kids 5-11 years old. Add-ons include drink tickets, medium pumpkins, apple cider donuts, carnival games, axe throwing, and Smashing Pumpkin alcohol shots. Tickets are offered for timeslots throughout the day and evening.