Look What’s Coming to Illinois for the Fall Season

The countdown to crisp nights, cozy sweaters, and pumpkin-spiced everything has officially begun. And this year, Illinois is welcoming back one of its most anticipated fall attractions: Jack’s Pumpkin Pop-Up. If you’ve been searching for the ultimate autumn adventure, look no further—this is where fall comes alive.

What Is It?

Jack’s Pumpkin Pop-Up isn’t your average pumpkin patch—it’s a two-acre, 100% outdoor fall playground that mixes tradition with over-the-top fun. Picture this:

Jack's Pumpkin Pop Up
Jack's Pumpkin Pop Up
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  • 10,000+ pumpkins spread across the grounds
  • A corn maze with a hidden bar inside
  • Food trucks serving up seasonal favorites
  • Craft beer & fall cocktails that taste like sweater weather in a cup
  • Fortune tellers ready to predict your spooky season future
  • Axe throwing for the adventurous
  • Carnival games that bring back childhood nostalgia
  • And endless photo ops

It’s the kind of place where you can sip cider, strike a pose in front of glowing pumpkins, and then get competitive tossing an axe—all in the same night.

Jack's Pumpkin Pop Up
Jack's Pumpkin Pop Up
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When & Where to Find It

This fall favorite is making its grand return in September 2025 in downtown Chicago at:
📍 1265 West Le Moyne, Chicago, IL 60642

Jack’s Pumpkin Pop-Up will officially be open for the fall season from September 18th – November 2nd, 2025.

Located right on Goose Island, Jack’s is the ultimate spot to soak up autumn in the city. Tickets aren’t on sale just yet, but they’ll be dropping soon—and if history is any indicator, they’ll go fast.

Jack's Pumpkin Pop Up
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Who Can Go?

The beauty of Jack’s is that it’s built for everyone:

  • All ages welcome
  • 21+ for drinking seasonal cocktails and craft beer
  • 18+ for axe throwing

So whether you’re planning a family day, a night out with friends, or a fall date you’ll actually remember, Jack’s has you covered.

Jack's Pumpkin Pop Up
Jack's Pumpkin Pop Up
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Why You Can’t Miss It

Walking into Jack’s feels like stepping into an autumn wonderland. With pumpkins glowing around every corner, laughter spilling out of the corn maze, and the smell of cider in the air, it’s impossible not to get swept up in the magic of the season.

Fall only comes once a year, and Jack’s Pumpkin Pop-Up is where you’ll want to spend it. So grab your flannels, rally your friends, and clear your calendar—Jack’s is back, and it’s bigger, brighter, and more “fall AF” than ever.

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LOOK: How Halloween has changed in the past 100 years

Stacker compiled a list of ways that Halloween has changed over the last 100 years, from how we celebrate it on the day to the costumes we wear trick-or-treating. We’ve included events, inventions, and trends that changed the ways that Halloween was celebrated over time. Many of these traditions were phased out over time. But just like fake blood in a carpet, every bit of Halloween’s history left an impression we can see traces of today.

Gallery Credit: Brit McGinnis

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