🎃Jack's Pumpkin Pop Up is Back September 2026! Jack’s Pumpkin Pop-Up is Chicago’s ultimate all-ages fall destination - an immersive festival experience packed with seasonal cocktails, carnival games, axe-throwing, a giant corn maze, and endless photo moments surrounded by thousands of pumpkins. It’s all ages, all the time: picture-perfect days for families and kids, then after dark the lights kick in, the energy turns BOO-zy, and the whole place transforms into a fall festival party. From sipping drinks under the lights to getting lost in the maze with your crew, every corner is designed for big laughs, good vibes, and the kind of nights you’ll want to relive all season. It’s part festival, part party, and all fall- Chicago’s go-to spot
If you're jonesing for a real Christmas tree this year, there's a new pop-up to check out: From the same folks who brought us Jack's Pumpkin Pop-Up comes Jack Frost Winter Village. The 2-acre attraction boasts a sprawling Christmas tree farm, photo opportunities and a dazzling, light-filled jaunt that's perfect for families who want to get some fresh air this winter. Tickets are available now and allow parties to explore the grounds for an hour and a half?the most affordable pass goes for $21 per person and includes Jack's Winter Walk and a Christmas doughnut (though a Christmas tree will cost extra, of course).
