Think you didn't have pick-your-own apple and pumpkin options living in an urban giant like Chicago? Think again!
The farms and orchards we've gathered here aren't too far from Chicago, and the trip will be well worth it when you're eating fresh, homemade pie and donuts while sipping some warm apple cider.
So round up the family, load up the car, and hit the road!
Image via Facebook/All Seasons Apple Orchard
14510 IL Route 176, Woodstock, IL
For $17 per person, you can pick from a wide range of apples at All Seasons Apple Orchard. Once you're done picking, hit the corn maze, pumpkin patch, and many more fall festivities! The farm market and country kitchen are free to visit, so stock up on delicious bites.
Distance from Chicago: 1 Hour, 10 Min to Woodstock, IL
Image via Facebook/Jonamac Orchard
19412 Shabbona Rd., Malta, IL
Ever wonder what would happen if you shot an apple or a pumpkin out of a cannon? Well, wonder no more! Find out for yourself at Jonamac Orchard and—once you've had your fill of pumpkin destruction—check out the orchard, play area, sunflower field, corn maze, petting zoo, and more. You can also reserve a private campfire site to end your group outing!
Distance from Chicago: 1 Hour, 15 Min to Malta, IL
Image via Facebook/Apple Holler
5006 S. Sylvania Ave., Sturevant, WI
Apple picking sure can make you hungry. So once you've picked your fill at Apple Holler, head on over to their outdoor orchard market and cider & bakery barn for apple cider donuts, homemade pies, deli sandwiches, and more! They've also been voted one of the top places to go apple picking across America, so go ahead and make some memories.
Distance from Chicago: 1 Hour to Sturtevant, WI
Image via Facebook/Lincoln Park Zoo
2001 N. Clark St., Chicago, IL
Right in the heart of Chicago, Lincoln Park Zoo's Fall Fest offers many seasonal farm activities without having to leave the city. As always, entry is free and you can purchase attraction tickets to check out the pumpkin walk, patch, and more. Stay tuned for special weekly events and Halloween pop-ups!
Distance from Chicago: Right in the city, baby!
Image via Facebook/Odyssey Fun Farm
18900 Oak Park Ave., Tinley Park, IL
True to its name, Odyssey Fun Farm offers many fun and exciting activities. With a petting zoo, cow train, hayrides, corn mazes, ziplining, and zombie paintball, there's something for everyone. While you won't find an orchard at Odyssey, there still is a pumpkin patch where you can take home the perfect pumpkin.
Distance from Chicago: 30 Minutes to Tinley Park, IL
Image via Facebook/County Line Orchard
200 S. County Line Rd., Hobart, IN
At County Line Orchard, you can pick apples, pumpkins, and sunflowers or take a stroll through their corn maze. After you've wrapped up in the orchard, make sure to grab some of County Line Orchard's famous apple cinnamon donuts. And by "some," we mean at least a dozen.
Distance from Chicago: 1 Hour to Hobart, IN
Image via Facebook/Siegel's Cottonwood Farm
17250 Weber Rd., Lockport, IL
Siegel's Cottonwood Farm has a flower and garden center for all your gardening needs – and for those of you that need a little more fun, they've also got over 35 attractions to choose from. Take a walk through the 12-acre corn maze, hitch a hayride, pick a pumpkin, play a game of giant checkers and so much more.
Distance from Chicago: 1 Hour to Lockport, IL
Image via Facebook/Stade's Farm and Market
3709 Miller Rd., McHenry, IL
Not only can you pick apples and pumpkins at Stade's Farm & Market, but you can also grab raspberries, green beans, tomatoes, and more (depending on the season, of course). The only thing more plentiful than the u-pick options is their list of fall attractions and activities.
Distance from Chicago: 1 Hour, 20 Min to McHenry, IL
Image via Facebook/Prairie Sky Orchard
4914 N. Union St., Union, IL
Prairie Sky Orchard offers apple and Asian pear picking at low prices. Make sure to stop by their store afterward for homemade jams, salsa, honey, and more tasty treats! Feeling hungry while you're there? No worries, their Koffee Kiosk is stocked with hot dogs, apple cider donuts, and Starbucks coffee!
Distance from Chicago: 1 Hour, 15 Min to Union, IL
Image via Facebook/Sonny Acres
29W310 North Ave., West Chicago, IL
Family-owned and operated since 1883, Sonny Acres Farm often chooses to do things the old-fashioned way. However, that hasn't stopped them from adding modern rides and attractions to their farm like the Haunted Hayride, petting zoo, pony and camel ride, and more!
Distance from Chicago: 1 Hour to West Chicago, IL
Image via Facebook/Pumpkin Farm
13341 W. 154th St., Homer Glen, IL
The fine folks at Bengtson's Pumpkin Farm claim they have a "billion gazillion" pumpkins. So whether you're looking to bake a pie or carve some up, it shouldn't be hard to find the perfect pumpkin for your needs. Bengtson's is now cashless – so come ready for a good time with the farm ride, animals, and delicious treats.
Distance from Chicago: 50 Min to Homer Glen, IL
Image via Facebook/Honey Hill Orchard
11738 Waterman Rd., Waterman, IL
Honey Hill Orchard keeps things simple with their apple, raspberry, and pumpkin picking. Things do get interesting at the bakery though which offers a wide selection of donuts and pies of various types. Satisfy any sweet tooth cravings here.
Distance from Chicago: 1 Hour, 15 Min to Waterman, IL
Image via Kroll's Farm
13236 Townline Rd., Waukegan, IL
You'll find all types of pumpkins at Kroll's Fall Harvest Farm, typically ranging from $1 to $50 depending on the size. Pumpkins are pre-picked and laid out by price along with gourds, Indian corn, straw bales, and corn stalk bundles. Make sure to hit the corn maze or petting zoo before heading home!
Distance from Chicago: 1 Hour to Waukegan, IL
Image via Facebook/Kuipers Family Farm
1N318 Watson Rd., Maple Park, IL
1N290 Watson Road (Pumpkins & Tulips)
1N145 Watson Road (Apples & Sunflowers)
Pick apples and pumpkins, stroll through the corn maze, or watch some pig races. These are only a few of the fun and wacky activities at Kuiper's Family Farm. Be sure to hit the Farmstand for super cute fall decor for your home!
Distance from Chicago: 1 Hour to Maple Park, IL
Image via Facebook/Goebbert's Pumpkin Patch
42W813 Reinking Rd., Pingree Grove, IL
Did you know Goebbert's Pumpkin Patch is home to a dinosaur? Don't worry. He only eats pumpkins. Say "hello" to this 20-foot dino then check out numerous other attractions like a haunted house, giant pumpkin slide, pony rides and so much more.
Distance from Chicago: 1 Hour to Pingree Grove, IL
710 W Boughton Rd., Bolingbrook, IL
There's never a dull day at Johansen Farms in Bolingbrook. The property is bustling with things to do (and memories to make). It's the perfect fall festival that's worth the 1 hour drive.
Distance from Chicago: 1 Hour to Bolingbrook, IL
Image via Facebook/Royal Oak Farm Orchard
15908 Hebron Rd., Harvard, IL
Home of the first apple tree maze of its kind in the U.S., Royal Oak Farm Orchard's Amaze N' Apples maze boasts 1.5 miles of winding trails that cover 5 acres! Pick an apple or two while you make your way 'round the maze, then stop by the orchard to grab some more to take home.
Distance from Chicago: 1 Hour, 30 Min to Harvard, IL
IMAGE VIA McHenry County
900 English Prairie Rd, Spring Grove, IL
Get lost among fields of pumpkins, corn mazes, and fall fun at Richardson Adventure Farm. It’s the perfect place to grab a cozy sweater, sip cider, and snap the kind of photos that make friends jealous.
Distance from Chicago: 1 Hour, 30 Min to Spring Grove, IL
Photo Via Keller's Farmstand
2500 Johnson Rd, Oswego, IL
516 Knoch Knolls Road, Naperville, IL
15066 S Wallin Dr, Plainfield, IL
A place where the legacy of generations meets the freshness of today. Explore Keller's inviting farmstands in Naperville, Plainfield, and Oswego, where you'll discover an array of homegrown vegetables, sweet corn that's simply irresistible, and the delight of picking your own apples in their expansive orchard.
Distance from Chicago: 1 Hour, 2 Min to Oswego, IL
Distance from Chicago: 50 minutes to Naperville, IL
Distance from Chicago: 54 minutes to Plainfield, IL
Updated September 2025
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