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Downtown Chicago's Pumpkin Patch Experience

Visiting Jack’s Pumpkin Pop-Up

Author: Ruby Travels


Returning to a two-acre plot of land just west of Goose Island, Jack's Pumpkin Pop-Up saves you a trip to the suburbs by bringing a corn maze, thousands of pumpkins, and plenty of Insta-worthy fall moments to Downtown Chicago. This year’s edition has a different look this year, with safety being their first priority (think mandatory timed reservations, face masks required, cash-less transactions, and no food and beverages onsite), but as Jack said, “the show must go on.”






The need to Knows before visiting Jack's pumpkin pop up

  • You must pre-purchase your ticket, you can do that here

  • Face masks must be worn at all times… cause ya know, COVID-19

  • No food or drink is available for purchase

  • 100% cashless, so leave those dollar bills at home

How do you get there

By Bus

If you are traveling by bus, you can reach Jack’s Pumpkin Pop-Up via routes 73, 56, and 72 (from Armitage Pl).

By Car

If you are traveling by car, you can find free street surrounding Jack's Pumpkin Pop-Up that is available on a first-come-first-serve basis...this is Chicago you know!

Alternatively, ride-share services from Francis and Armitage Houses take ~15-minutes and costs between $10-20.

By Foot

If you plan on walking, wear a warm coat with it taking ~40-minute from Armitage Pl.

By Bike

If you plan on biking, take the scenic route and bike along The 606 to arrive in ~15-minute from Armitage Pl.


Jack’s Pumpkin Pop-Up Highlights:

Corn Maze

Did someone say Downtown Chicago’s largest corn maze?! Sign us up! Explore the twist and turns, and keep an eye out for the exciting photo opportunities inside the maze.


Pumpkins, Pumpkins, Pumpkins Who would’ve thought there would be pumpkins at Jack’s Pumpkin Pop Up?! Don’t forget to pick your perfect pumpkin to take home. They also make a great pop for all the snaps we know you’ll be taking.



Instagrammable Fall Moments Talk about Instagram heaven. With over 20 stations, you’re bound to snap the perfect Instagrammable fall moment, without even having to leave Downtown Chicago. Check out their Instagram for your Fall pic inspo. We’ve done the groundwork for you and collected our favorite Instagram captions:

  • Pumpkin kisses and harvest wishes

  • Pumpkin is the spice of life.

  • Pumpkin spice and everything nice

  • Oh my gourd, I love fall

  • Autumn leaves and pumpkins, please







#Views If you look South you’ll catch a glimpse of our favorite skyline. Keep an eye out for the Willis Tower poking out. The skyline looks its most magical right around sunset, so we recommend getting there between 4-6 pm so you don’t miss it!






Don’t miss out on the Fall Festivities! Jack’s Pumpkin Pop-Up is open until November 1 so get your tickets here and make the most of Fall 2020. For more of my adventures, follow Ruby Travels on Instagram. Want to find out more about living in Chicago? A co-living space in Chicago may be exactly what you’re looking for. Explore co-living spaces in Chicago neighborhoods today.




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