Jack’s Pumpkin Pop-Up fills 2 acres on Chicago’s Goose Island with more than 10,000 pumpkins, a corn maze with a hidden bar at the end, carnival games, axe throwing, gem mining and apple cider donuts, all with the skyline behind it. It runs Sept. 19 through Nov. 1, every day, rain or shine, and it is a long drive from Indianapolis, about three hours up I-65. That makes it a longer haul than most of our day trips from Indianapolis, so pair it with a weekend in the city, or stop at Fair Oaks Farms on the way up.
Jack’s Pumpkin Pop-Up 2026: Dates, Hours and Tickets
- Dates: Sept. 19 through Nov. 1, open every day. The last weekend is Oct. 31 to Nov. 1.
- Entry times: Tickets are timed, every 30 minutes, and you need to arrive within 30 minutes of the time on your ticket. Entry slots run 4 to 9 p.m. Monday through Wednesday, 4 to 9:30 p.m. Thursday and Friday, 11 a.m. to 9:30 p.m. Saturday and 11 a.m. to 9 p.m. Sunday, all Central time. The last tickets sell 90 minutes before closing.
- Where: 1265 W. Le Moyne St., Chicago, on Goose Island. There is no parking lot; Jack’s recommends ride-share, and the address doubles as the drop-off point.
- Tickets: Prices change by date and time. For the rest of the season, a basic Entry and Corn Maze ticket ran about $34 to $45 with fees when we checked, with weekend afternoons at the top of that range. The kids ticket covers ages 5 to 11 and costs a few dollars less; 12 and up pay the adult price; kids 4 and under are free with a paid adult. Buy at jackspumpkinpopup.com.
- Good to know: No re-entry, but you can stay as long as you like. It is 100% cashless and outside food is not allowed. Sales are final; you get one exchange to another date through the link in your confirmation email, and you pay any price difference. If it rains, your ticket is good any time that day.
Pick a Time: Family Hours vs. Night Hours
Jack’s draws two different crowds. Before 7 p.m. it is aimed at families. After 7, it turns into a grown-up night out with three full bars, and anyone under 18 has to be with an adult. With kids, book a weekend morning or a weekday slot right at 4 p.m.; you get daylight in the maze before the bar crowd shows up.
What’s Included and What Costs Extra
Every ticket includes entry, the corn maze and the photo spots. Everything else is a package or an add-on, and the packages come out a dollar or two cheaper than buying the pieces separately. Two Spooky, for two guests, gives each person entry, three drinks, a pumpkin, three donuts and 10 carnival tickets; the Family 4-Ever package for two adults and two kids shows up on some weekday dates. If you buy as you go, it looks like this, before the fees added at checkout:
- Pumpkin under 11 pounds, $7; jumbo pumpkin, $9
- Apple cider donuts, $3.50 each or six for $18
- 20 carnival game tickets, $18
- Gem mining, a 5-pound bag for the sluice, $15
- Axe throwing, three throws, $10 (18 and up)
- Hot cider or hot chocolate, $7 at the bar. The bars take cards, but prepaid drink tickets, the kind that come in packages, have to be bought before you go in.
Fortune tellers are on site for an added cost, first come, first served.
The Corn Maze
Jack’s bills it as the largest and only corn maze in downtown Chicago. It takes 20 to 45 minutes, and the finish line is a hidden bar for the grown-ups. For mazes you can reach without a hotel, see our list of corn mazes near Indianapolis.
The Pumpkin Patch and Photo Spots
More than 10,000 pumpkins are stacked into arches, walls and a pumpkin house, with the city lights coming on behind them at dusk. Taking one home takes a pumpkin package or add-on, or you can buy one in the patch. Jack’s is upfront that it is not a farm: no hayrides, no petting zoo. If that is what your kids are after, stick with the pumpkin patches near Indianapolis.
Apple Cider Donuts
The donuts are the thing people line up for, and food trucks come in on select weekend nights. If you can’t make the drive, the best apple cider donuts in Indianapolis are a lot closer.
Carnival Games, Gem Mining and Axe Throwing
The carnival midway runs on tickets, and the gem-mining sluice is the hit with younger kids, who keep what they find. Axe throwing is for 18 and up, in an outdoor range, and closed-toe shoes are required.
Tips for the Trip
- Mind the time zone. Chicago is on Central time, an hour behind Indianapolis. Your 4 p.m. ticket is 5 p.m. on the car clock.
- Plan the parking. There is no lot on site, so book a garage nearby or park once at your hotel and take a ride-share.
- Dress for a field. It is all outdoors on straw, hay and gravel. Strollers, wagons and wheelchairs are allowed, but it is a bumpy push; restrooms are portable toilets.
- Leave the dog home. Only service animals are allowed, and bags are checked at the gate.
- Buy ahead. Walk-up tickets are sold if a slot hasn’t sold out, but they usually cost more.
- Check the email, not the ticket. The mobile ticket lists only entry, the maze and axe throwing. Donuts, pumpkins and game tickets show up when your code is scanned at the gate.
For more fall plans closer to home, see our fall fun in Indianapolis list.
