Think you didn't have pick-your-own apple and pumpkin options living in an urban giant like Chicago? Think again!
I've had that Trader Joe's Pumpkin Pie Spice sitting in my cabinet for wayyy too long, so I'm considering it a sign to take that Chicago wind to the outskirts and pick some dang apples myself. Obviously, I'm using it as an excuse to break out my tastefully eclectic cowboy boots that I thrifted with my I'll-wear-this-every-day mentality and have actually never let them see the sun since. Also, apparently there are more than 2,500 apple varieties in the US? News to me.
Let me read you my to-do list for today: churn out the most epic and spiciest cosmic apple pie on EARTH. I'd like to see you top that.
Image via Facebook/Pumpkin Farm
13341 W. 151st St., Homer Glen, IL
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The fine folks at Bengtson's Pumpkin Farm claim they have a "billion gazillion" pumpkins. Whether you're looking to bake a pie or carve one up, it shouldn't be hard to find the perfect pumpkin for your needs. Come ready for a good time with the farm ride, animals, and delicious treats. Bengtson's is now cashless.
Hours: Sept. 4–Nov. 8; Mon–Fri 11am–8:30pm, Sat–Sun 10am–8:30pm.
Distance from Chicago: 50 Min to Homer Glen, IL
Image via Facebook/All Seasons Apple Orchard
14510 IL Route 176, Woodstock, IL
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If I'm committing to an apple-picking day, I appreciate having options. All Seasons has thousands of apple trees to wander through, plus a corn maze, pumpkin patch, petting zoo, sunflower trail, apple cannon, and enough other fall activities to keep me occupied. I'm also leaving room for an apple cider donut before heading back to the metropolis.
Hours: Open Aug. 29-Nov. 1; hours vary by date, so check the farm's calendar before speeding out.
Distance from Chicago: 1 Hour, 10 Min to Woodstock, IL
Image via Facebook/Jonamac Orchard
19412 Shabbona Rd., Malta, IL
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If I'm making the trek out to Malta, you best believe I'm making a whole fall day of it. Jonamac has pumpkins, cider, a daytime corn maze, an apple cannon, and plenty of other farm activities. Still, I'd save a little energy for October nights, when the maze turns into a full-on Haunted Corn Maze with scare actors hiding among the stalks. BOO! Haha, I stole your pumpkin while you weren't looking.
Hours: Daily, 9am-5:30pm during the fall season. Haunted Corn Maze: Fri + Sat in Oct, sunset-10:30pm.
Distance from Chicago: 1 Hour, 15 Min to Malta, IL
Image via Facebook/Apple Holler
5006 S. Sylvania Ave., Sturevant, WI
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Apple picking has a funny way of making me hungry right away, so Apple Holler understands the assignment. Once I’ve wandered through the orchard, I’m heading straight for the farm store and bakery for cider, apple cider donuts, pies, and whatever else smells good enough to derail the rest of my plans.
Hours: Farm Store & Bakery Mon–Fri 8:30am–5pm; Sat–Sun 8:30am–6pm. Orchard admission hours may differ.
Distance from Chicago: 1 Hour to Sturtevant, WI
Image via Facebook/Lincoln Park Zoo
2001 N. Clark St., Chicago, IL
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I have to be honest, sometimes I want fall without spending half the afternoon on the Kennedy, and Lincoln Park Zoo makes that very possible. Fall Fest brings pumpkins, seasonal food, live entertainment, rides, photo ops, and pumpkin carving right into the city, so I can get my autumn fix and still be home before dark. Stay tuned for special weekly events and Halloween pop-ups!
Fall Fest Hours: Sept. 25–Nov. 1, 10am–5pm, Fridays–Sundays. Zoo grounds are open daily 8am–5pm.
Distance from Chicago: Right in the city, baby!
Image via Facebook/County Line Orchard
200 S. County Line Rd., Hobart, IN
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I’m going to County Line with two goals: pick apples and leave with an unreasonable number of apple cinnamon donuts. There’s also a corn maze, pumpkin and sunflower picking, farm animals, and plenty of room to make an entire fall day out of it, though the orchard notes that its 2026 U-pick apple crop is more limited than usual.
Hours: Big Barn daily 8am–6pm; outdoor attractions 9am–5pm.
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 who need a little more fun, they 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.
Hours: Pumpkin Fest runs daily 10 am–6 pm from late September through Halloween.
Distance from Chicago: 1 Hour to Lockport, IL
Image via Facebook/Stade's Farm and Market
3709 Miller Rd., McHenry, IL
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When I want the apple-orchard experience with enough extras to turn it into an all-day outing, Stade’s is an easy pick. Beyond picking, I can hit the petting zoo, corn maze, giant slides, hayrides, jumping pillows, farm train and plenty more without having to settle for the vague “fall activities” description.
Hours: Farm Market 9am–6pm; Pick-Your-Own 9am–5pm when available; Farm attractions 10am–6pm when available.
Distance from Chicago: 1 Hour, 20 Min to McHenry, IL
Image via Facebook/Sonny Acres
29W310 North Ave., West Chicago, IL
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I can definitely appreciate a farm that’s been around since the 1800s but still knows when to add a little chaos. Sonny Acres mixes classic pumpkins and hayrides with amusement rides, a petting zoo, food, live entertainment, and, once night falls, its Haunted Hayride and Haunted Barn.
Fall Festival Hours: Sept. 19–Oct. 30. Most daytime attractions begin at 10am; closing times vary by date and attraction! Generally closed Mondays.
Distance from Chicago: 1 Hour to West Chicago, IL
Image via Facebook/Honey Hill Orchard
11783 Waterman Rd., Waterman, IL
Honey Hill is where I'd go when I want my fall plans simple: apples, pumpkins, cider, and baked goods. There are 25 apple varieties, an old converted Apple Barn relic, a petting zoo, and a straw maze, but I'm probably spending an embarrassing amount of time deciding between cider donuts and pie. Can you tell by this article how many cavities I've had?
Hours: Sept. 4–Nov. 8; 9am to 5:30pm through Halloween.
Distance from Chicago: 1 Hour, 15 Min to Waterman, IL
Image via Kroll's Farm
13236 W. Townline Rd., Waukegan, IL
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Kroll’s is less “apple orchard” and more classic fall farm, so I’d come here when pumpkins, hayrides, animals, and getting strategically lost in a corn maze are the priority. Their 2026 maze celebrates 250 years of America through farming history, and the farm also has a petting zoo, pumpkin picking, and concessions.
Hours: Thurs 1–8pm; Fri 10am–8pm; Sat–Sun 10am–7pm; Mon–Wed closed. Seasonal schedule runs Sept. 19–Oct. 31.
Distance from Chicago: 1 Hour to Waukegan, IL
Image via Facebook/Kuipers Family Farm
1N145 Watson Road (Apples & Sunflowers)
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Kuipers is the kind of place where my “quick apple-picking trip” is probably turning into several hours. There are U-pick apples, pumpkins, and a full Fall Harvest Fest, plus enough farm activities and bakery treats that I should probably stop pretending I’m there solely for produce. Here’s the best part: pig racing. I’ll race you back to Chicago on three.
Hours: Fall Harvest Fest Sept. 18–Nov. 1; orchard operations begin in August. Daily opening times vary by date, generally beginning at 9 or 10am and running to 6pm, so check the farm calendar for the date you’re visiting.
Distance from Chicago: 1 Hour to Maple Park, IL
Image via Facebook/Goebbert's Pumpkin Patch
42W813 Reinking Rd., Pingree Grove, IL
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Y’all ever seen Jurassic Park? I’m not sure how many pumpkin patches can say they have a dinosaur, but that alone gives Goebbert’s a pretty unfair advantage. Don't worry, he only eats pumpkins. Once I’ve witnessed that masterpiece, there are more than 40 other attractions to explore, including wagon rides, farm animals, slides, a train, and a freaking carousel.
Hours: Mon–Wed 9am–6pm and Thu–Sun 9am–8pm.
Distance from Chicago: 1 Hour to Pingree Grove, IL
Image via Johansen Farms Children's zoo & Pumpkin patch
710 W Boughton Rd., Bolingbrook, IL
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Johansen is where I’d go when my fall agenda is basically pumpkins, baby animals, and rides I’m too uncomfortably old for. The Children’s Zoo and Fall Festival pack in the family attractions, but I’m absolutely making a bakery stop too: their hot apple cider donuts are one of the farm’s signature treats, alongside fresh pies, turnovers, and breads.
Hours: Free Open Market + Pumpkin Patch 9am–6pm daily; Children’s Zoo 10am–6pm daily. This season runs through Nov. 1!
Distance from Chicago: 1 Hour to Bolingbrook, IL
Image via Facebook/Royal Oak Farm Orchard
15908 Hebron Rd., Harvard, IL
If I’m going to get lost in a maze, I might as well do it among apple trees. Royal Oak’s Amaze ’N Apples is billed as the first maze of its kind in the U.S., with trails winding through the orchard itself. If I ever escape, there’s still a bakery, petting zoo, playground, flowers, and plenty more to keep me from immediately heading back to Chicago. As if I could possibly do that.
Hours: Aug. 21–Oct. 31; Mon–Thu 10am–5pm, Fri–Sun 10am–6pm.
Distance from Chicago: 1 Hour, 30 Min to Harvard, IL
IMAGE VIA McHenry County
909 English Prairie Rd, Spring Grove, IL
If I want to go way beyond apple picking, Richardson is basically fall turned up to an 11 out of 10. The centerpiece is its enormous 28-acre corn maze, plus slides, rides, and a long list of farm attractions, so I’d budget a few hours instead of trying to squeeze it into the afternoon.
Hours: Sept.: Fri 3–11pm, Sat 10am–11pm, Sun noon–9pm. Oct.: Thur 3–9pm, Fri–Sat 10am–11pm, Sun noon–9pm. Open through Nov. 1.
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
Do you smell that? The sweet whiff of homegrown vegetables, corn (which I used to eat exclusively as a kid), apples, and… you guessed it, even more apples. Keller’s has been open for generations, so I think it's time we meet the ghosts.
Hours: Mon-Fri 10am-6pm; Sat-Sun 9am-5pm
Distance from Chicago: 1 Hour, 2 Min to Oswego, IL
Distance from Chicago: 50 minutes to Naperville, IL
Updated October 2026
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