jack's pumpkin pop up logo

When you think of fall pumpkin festivals it usually involves schlepping the whole family to a distant suburb and soberly bearing through the whole experience.  Well city dwellers schlep no more.  Jack’s Pumpkin Pop-Up is the perfect answer to having fall fun with a delicious cocktail and even some axe throwing right in the heart of Chicago.

Jack's Pumpkin pop-up

Family Fun 411 was invited as complimentary guest of Jack’s Pumpkin Pop-Up, all opinions are completely my own based on my experience.

This is a great option for fall fun in the city.  Understand that it is a Pop-Up in an empty lot not a pumpkin farm.  They do a great job of bringing in all elements of fall.  Haystacks, pumpkins, scarecrows, and all the standard Halloween props. 

There are plenty of social media worthy photo backdrops.  If you are not camera shy and you can spend some time getting the perfect shots.  Bring out your fall boots and over sized sweaters and strike a pose!  If you are bringing little ones, you’ll have the cutest photos to send to the grandparents.

Pumpkin Pop-Up Fun

Jack’s Pumpkin Pop Up very clearly advertises that after 7pm it is boo-zey and geared towards adults.  With 4 bars I would agree.  Other than the corn maze there is not too much for little ones to do.  My toddler’s favorite thing was this weird over sized impression toy.  That captivated him for most of the time.  The elementary aged child in our group played the arcade and carnival games and had fun winning a stuffed toy prize.  The arcade games are extra and not included in the admission. 

pumpkin pop-up corn maze

The corn maze by far was the most fun.  We completely failed.  It is tricky.  Somehow, we ended up back at the entrance much to our surprise.  I could only imagine at night being scared by some of the surprises in the corners! The terrain in the corn maze is not ideal for strollers. The other attraction is the axe throw. 

Food and Drinks

The food was standard outdoor event fare of hotdogs and burgers.  There were also food trucks selling barbeque and Mexican.  If you’ve been following me, you know I never pass up on elotes and it was a huge portion for $4.  My son enjoyed a cheese quesadilla.  The fall themed cocktails are creative and delicious.  Note that the bars accept credit cards only. No cash.

What really makes this an urban experience is the pop music playing in the background, the lights creating a cool ambience and the bars. 

This is the type of place I would come back to at night with a group of my friends and a designated driver. 



There is street parking available.  Spots are limited.  Valet parking is available. 


1465 N. Elston Ave.

Chicago, IL 60642


Monday – Fridays 4pm -10pm

Saturdays and Sundays 11am – 10pm

Runs until Sunday, November 3rd


Children 5 and under are Free

General admission arrive between 11am – 2pm $15

General admission arrive between 2pm – 9pm    $19

Kids General admission (ages 5-12)           $12pm

Other ticket options available based on drink tickets and axe throws.


Jack’s Pumpkin Pop-Up

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