Hey, Illinois parents! Save the dates in your calendar now because Jack’s Pumpkin Pop Up is rolling back into Chicago soon, and it’s ready to sprinkle magic all over fall family time again!

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Fall Plans in Illinois

You know what happens in my house each summer when the heat really cranks up and the calendar is ready to flip to August? Our brains automatically switch into Fall mode!

Summer lovers, please don't get mad at me for saying that, my family enjoys summer too, but we have a real soft spot for all things pumpkin, cider donuts, and harvest fun.

READ MORE: Opening Dates For Popular Northern Illinois Apple Orchards

Now that we're officially in the part of summer where fall events and save the dates start getting announced, there's one fall attraction returning to Chicago this September that you'll definitely want to save some time to visit.

Jack's Pumpkin Pop Up Is Returning to Chicago

In 2024, thousands of people flocked to Goose Island in Chicago for a truly spectacular event, Jack's Pumpkin Pop Up:

 

Things to See and Do at Jack's Pumpkin Pop Up

One thing I love about holiday pop-ups like this is the "go big or go home" attitude and look of them. For example, why have just 10,000 pumpkins, when you could have way more? Why have just a few orange decorations and lights when you can have the whole place looking like a sea of orange? I think you get my point...

Here are some more attractions your family can enjoy at Jack's Pumpkin Pop Up:

  • Chicago's largest corn maze
  • Instagram‑worthy photo ops
  • Carnival games and other activities for kids
  • Fortune tellers
  • Axe throwing (18+)
  • Dueling mechanical bulls & pig races
  • Food trucks & seasonal treats
  • Full bars + fall cocktails (21+)

An official opening date for 2025 Jack's Pumpkin Pop Up has not been announced yet, but I can guarantee it will be sometime in September! Keep a close eye on jackspumpkinpopup.com for more information coming soon!

Wisconsin Home Named Among Best Airbnbs to See Fall Foliage in America

5 Perfect for Fall Apple Orchards in Northern Illinois to Visit

Illinois summer lovers will tell you that deep down, they can't wait for a fall trip to an apple orchard. We're blessed to have some great orchards so close.

Gallery Credit: Steve Shannon