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Jack’s Pumpkin Pop-Up 2021

September 28, 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!

  • Go Your Own Way Black Fringe Sweater
  • Beautiful Sound Cream A-Line Suede Skirt
  • Similar black heeled boots: Option 1, Option 2, Option 3

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.

Filed Under: Chicago, Lifestyle, Seasonal Tagged With: chicago, chicago event, jacks' pumpkin pop up, Pop Ups

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About Alyssa

Alyssa is a lifestyle writer living in downtown Chicago. Her blog, Sweating Champagne, focuses on local events & festivals, mental health awareness, travel guides, and style. She loves urban living, personality quizzes (ISTP!), reading fantasy novels, listening to music, and hanging out her two cats.

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