The Ultimate Chicago Fall Bucket List
The Ultimate Chicago Fall Bucket List

The Ultimate Chicago Fall Bucket List

Let the pumpkin spice rain down on us! πŸŽƒ

Published September 21, 2021

As humidity makes its grand exit (please, just leave) and the temperature drops, we've begun to master the art of layering. With fall officially upon us, we're no longer ignoring our desire for pumpkin beers, cozy sweaters, and three Starbucks spiced lattes a day. Tis' the szn for spooks, scares, and stockpiling mini gourds and candy corn (who can resist, really?). 

So, break out those casper the ghost socks and get ready to take a sip of this tea (and by tea we mean our Official Fall Bucket List)! 

Spring Awakening Music Festival

Bucket Listers is pumped to provide exclusive ticket pricing for the largest dance music fest in the midwest: Spring Awakening Music Festival! The 2021 catch? Spring Awakening will be held in Fall. Headliners Martin Garrix and Excision are just the tip of the iceberg of the EDM spectrum you’ll get with this festival's 7th anniversary, along with mesmerizing pyrotechnics, carnival rides, and more. 

Ticket: GA Single Day: $89 per person (originally $99)
When: Saturday, October 2 and Sunday, October 3; 1:00 PM - 10:00 PM
Where: Addams/Medill Park: 1301 W. 14th Street, Chicago, IL, 60608

For more information on the Spring Awakening Music Festival.

Statesville Haunted Prison

Statesville Haunted Prison, widely known as Illinois’ best haunted house, is in its FINAL season after 25 years of screams and thrills. Don't miss your last chance to find your way through 23 maximum security cells and come eye to eye with over 100 criminals that were too evil to die...

Ticket: GA is $30. 
When: Opening day is Oct 1st 2021 at 7pm, then Thursdays-Sundays, and Halloween Night open 7 PM—11 PM.
Where: 17250 Weber Rd Lockport, IL 60441

For more information on Statesville Haunted Prison.

Museum of Illusions’ Spooky Hours

You never know what's around the corner at Museum of Illusions πŸ‘€ πŸ‘» Enter the wonderful world of illusions where you can truly experience the impossible. Illusions challenge us to see things differently and they reveal a lot about how our brain interprets reality. This fall, you can visit the Museum of Illusions Chicago for a spooky, Halloween themed night at the museum where nothing is quite as it seems. 

πŸŽƒ What's Included: 
- New Halloween themed decor and exhibits
- 2 drinks included in ticket price (wine + beer) provided by Left Coast
- Live, strolling magician

Tickets: $45 per person
When: September 30, October 7, 14, 21; Entry at 8PM or 8:45PM
Where: 25 E Washington St.,Chicago, Illinois

For tickets to Spooky Hours at Museum of Illusions.

Jacks Pumpkin Pop Up

Nothing says spooky sun quite like the biggest pumpkin patch pop-up in the heart of Chicago! Join Jack’s Pumpkin Pop-Up for the newest interactive experience to hit Chicago, located on over 2 acres in Goose Island. Spend an autumn night outside making memories without having to travel to the Suburbs while you get lost in Chicago’s largest corn maze! Whether you’re seeking a striking nighttime lights display, an outdoor pumpkin-themed party with dozens of fall themed instagramable memories or a one of a kind corn maze, there’s an experience here for everyone

Where: 1465 N. Elston Ave., Chicago, IL 60642
When: Running September 23 - October 31

For more information on Jack's Pumpkin Pop-Up.

Spray Paint n Sip

Unleash your inner street artist for a Spray Paint ‘n’ Sip Class. Looking for a fun and unique way to tap into your creativity? This interactive urban art workshop allows you to create your very own original piece. And the best part? It’s BYOB. Cheers!

Tickets: $35 per person 
When: Wednesdays - Sundays
Where: Chicago Kedzie Plaza- 800 N. Kedzie, Chicago IL 60651

Purchase tickets to Spray Paint ’n’ Sip.

Goebbert's Farm 

Trick or treat yourself to Goebbert’s Pumpkin Patch & Apple Orchard. Their Fall Festival is everyday until Halloween, offering a full day of family-friendly activities that are sure to delight kids and grown-ups of all ages. The General Admission fee includes almost all of the activities on the Farm. 

When: August 27 - Halloween from 9am-6pm
Where: 42W813 Reinking Road Pingree Grove, IL 60140 

For more information on Goebbert’s Farm.

Run The Chicago Marathon on Oct. 10

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Whether you're an elite athlete looking to flex your status, an everyday runner ready for a new challenge, or just looking to get into some Nike swag (read: us): the legendary Chicago Marathon is calling your name. And most importantly, runners are invited to run on behalf of a charity of their choice. A wonderful way to start the giving season. 

When: Sunday, October 10th

For more information on the Chicago Marathon.

Tailgate and See the Bears Win at Soldier Field

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Tailgating is back at the stunning Soldier Field for 2021! Pack the coolers, brush on the face paint, and “Bear Down” for the season. 

Where: 1410 Special Olympics Dr, Chicago, IL 60605

Find the full Chicago Bears schedule here.

Art of Banksy Exhibit

The largest exhibit of the world’s most famous political street artist? Yeah, you don’t want to miss it. See the verified original, subversive masterpieces of the mysterious—still unidentified (!!)—Banksy in this unauthorized private collection. 

Ticket: $40
Where: 360 N State St, Chicago, IL 60654

For more information on the Art of Banksy Exhibit.

Lincoln Park Wine Festival

For the sixth year, Lincoln Park Wine Fest will transform tranquil Jonquil Park into an open-air market with wine, sangria and sparkling tastings from 25+ high-end world wide varieties. Vino, Wein, Vin, and did we say sangria? But here’s the best part...

Bucket Listers is excited to offer you exclusive ticket pricing:
VIP Tickets, only available on Bucket Listers: $65 per person
- (9) standard tastings + (6) speciality/exclusive tastings
- Complimentary full glass of wine
- Stemmed commemorative tasting glass
- VIP Tasting Area

GA Tickets: $30 per person (originally $43)
- (12) standard tastings
- Stemmed commemorative tasting glass
- Tasting access

When: Friday, Oct. 8th, 2021 at 5PM - 10PM, Saturday, Oct. 9th at 11AM - 10PM, Sunday: Oct. 10th at 11AM - 7PM
Where: Jonquil Park, 1001 W. Wrightwood Ave Chicago Illinois

For more information on Lincoln Park Wine Festival.

Stroll Through Millennium Park 

The park takes on a colorful facade in the fall and is open daily, 8am to 9pm. Stroll over to the adjacent Maggie Daley Park for a longer walk and mini golf. 

When: Open daily, 8am to 9pm
Where: 201 E Randolph St, Chicago, IL 60602

Watch A Halloween Movie at ChiTown Drive-In

Nothing says fall quite like your favorite halloween movies under the stars. Hocus Pocus, anyone? Last year for Halloween week, the drive-in even featured trick-or-treating...with costumes highly encourged.  

When: Various Dates Through Oct 31.
2343 S Throop St, Chicago, IL 60608, USA

For Tickets and Line-Up to ChiTown Drive-In

Apple Picking and Cider Donuts at County Line Orchard

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You know autumn is here when you see the leaves turning, temperatures dropping, and our faces stuffed with apple cider donuts (yesss, we ate the last one). Stop by the County Line Orchard to go apple and pumpkin picking, find your way through corn mazes, and don't you dare leave without a gallon of apple cider for the rest of us. 

When: Until October 31st
Where: 200 S County Line Rd, Hobart, IN 46342

For more information on County Line Orchard.

Road Trip to Starved Rock State Park  

Only a 90 minute drive from the city, you'll find an oasis filled with canyons and waterfalls. Starved Rock is the perfect getaway from the hustle of the city, all while staying close to the colors of autumn.  Pro Tip: Take time to visit some of the local wineries and breweries in the area.

When: All season long
Where: 2668 E 875th Rd, Oglesby, IL 61348

For more information on Starved Rock State Park.

Enjoy Fall Foliage at Chicago Botanic Garden

It’s the best time to get outdoors and see colorful foliage – sugar maple, oak, sassafras, magnolia & more. Tram Tours are offered daily through October, as well as virtual events online.

When: Daily 8AM - 5PM
Where: 1000 Lake Cook Rd, Glencoe, IL 60022

For more information on the Chicago Botanic Garden.

Find your way through the Richardson Corn Maze  

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Betcha didn't know the largest corn maze in the world is in Illinois, did ya? Yea, we just took the entire state and made it into a maze (only kidding). Many farms have cool corn mazes, but not many can live up to the size and detail of the Richardson Adventure Farm Corn Maze! With its 9 - 10 miles of trail winding through 28 acres of live corn, you are in for a challenge and a treat!

When: Open through October. 
Where: 909 English Prairie Rd, Spring Grove, IL 60081

For more information on the Richardson Adventure Farm. 


Fall at Lincoln Park Zoo

Fall fest returns to the Lincoln Park Zoo! This year, Lincoln Park Zoo will be adorned with carved pumpkins, corn husks, and hay bales—not to mention the crisp autumn breeze rustling orange and yellow leaves and fall temperatures favorable for outdoor animal viewing.

When:October 8–October 31
Where: 2001 N Clark St, Chicago, IL 60614

For more information on Fall Fest at Lincoln Park Zoo.


(Cover image courtesy of Todd R Photo Via Lincoln Park Zoo) 

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