The Ultimate Chicago Fall Bucket List

Chicago Bucket List By Chicago Bucket List

Let the pumpkin spice rain down on us! 🎃


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)! 

 
 
 
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Jack's Pumpkin Pop-Up 

Located near North and Clybourn, you'll find a Halloween pop-up filled with glowing pumpkins, a corn maze, and plenty of photo ops. Back by popular demand, Jack's is the perfect activity for a group, date night, or just generally for pumpkin lovers. If you choose to take your chances with the corn maze, you'll be rewarded with a boooo-zy bar hidden within. 

When: Beginning October 3rd, running 4 weeks only. 
Monday-Friday 4PM-10PM  / Saturday and Sunday 11AM-10PM 
Where: 1465 North Elston Avenue 

For more information.

Stroll Through Millennium Park 

The park takes on a colorful facade in the fall. Stroll through Maggie Daley park and take a stab at the skating ribbon or climbing wall. Then make your way to Grant Park to fall in love with the colors of Buckingham Fountain before it gets shut off for the cold season.

Pro Tip: Bring yourself to Cindy's Rooftop for an autumn-themed cocktail 13 stories above the park. The panoramic views will give you a different perspective (or vertigo?)! 

When: All season long.
Where: 201 E Randolph St, Chicago, IL 60602

 

Night of 1,000 Jack-O-Lanterns at Chicago Botanic Garden 

Every year the Chicago Botanic Garden brings artists from all over to carve intricate pumpkins– some as large as 150 pounds! The LED-lit jack-o’-lanterns will be staged along a festive, paved pathway through the garden, starting at the Esplanade - and they are drop dead gourd-geous. 

When: October 16th - 20th and 23rd - 27th from 6:30PM to 10:30PM.
Where: 1000 Lake Cook Rd, Glencoe, IL 60022

For more information. 

 
 
 
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Apple Picking and Cider Donuts at County Line Orchard

You know autumn is here when you see the leaves turning, temperatures dropping, and our faces stuffed with apple cider donuts (yess, we ate the last one). Stop by the County Line Orchard to go apple and pumpkin picking, find your way through corn mazes, kiddy farms, 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.


(Photo Credit: Todd R Photo)

Fall Fest at Lincoln Park Zoo 

Lincoln Park gets coated in color during the fall. Taking place every Friday through Sunday, the LP Zoo celebrates the arrival of sweater weather with their annual Fall Fest which includes activities like a pumpkin patch, ferris wheel, and drum roll please... a corn maze!

For the adults in the room, you'll find nightly activities like a dessert fest, haunted tours, harvest dinners, and adult nights. 

When: Friday through Sundays at 10AM - 5PM.
Where: 2001 N Clark St, Chicago, IL 60614

For more information.

Stroll The Riverwalk to Watch The New 'Art on theMart'

The Merchandise Mart is one of the largest buildings in Chicago by scale, so adding a massive digital projection over the Chicago River makes it that much cooler. Take a stroll along the riverwalk to experience this bucket list projection in person. Afterwards, walk on over to the City Winery for a glass of pinot (but that doesn't come in pumpkin spice, sadly.)

When: Running every Wednesday through Sunday until November 22 / Begins at sundown (6:30).
Where: Across from the Merchandise Mart (222 Merchandise Mart Plaza Suite 470 Chicago, IL 60654) on Wacker Drive. 

For more information.

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 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

 
 
 
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Statesville Haunted Prison

Is there a better way to celebrate the season of crying at scary clowns spooks than attending a Haunted House Prison? Statesville has been around for decades now and is one of the top Halloween activities in Illinois. Though a fictitious prison, the characters are based off of real inmates like John Wayne Gacy 🤡 annd that's our cue ... 

When: Thursday through Sundays
Where: 17250 South Weber Road, Lockport, IL 60441

For more information.

 
 
 
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Watch the Chicago Marathon on October 13th 

Don't want to take a leisurely 26.2 mile jog? OK, we get it. Come cheer on the runners instead! Pick a spot along the route through the city and become part of a support system for the runners. The community that shows up to cheer is truly inspirational and the signs they make are even better. Who knows, you may even sign up to run next year! 

When: October 13th with the first wave starts at 7:20 (the really really fast people). 
Where: Along the streets on Chicago, here's the route. 

For the official route map

 
 
 
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Find your way through the Richardson Corn Maze 

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). 

To celebrate the 50th Anniversary of Apollo 11 and man walking on the moon, the maze theme will revolve around space. So, good luck finding your way home from the corn-moon. 

When: Open through October. 

Where: 909 English Prairie Rd, Spring Grove, IL 60081

For more information

 
 
 
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Tailgate and Watch DA The Bears at Soldier Field

What is fall without da feeling of ten layers, three hats, two foot warmers, and a beer in hand? DA BEARS. Da iconic Soldier Field lights up for Da Bears games with clear eyed and full hearted Chicagoans - and trust us, there is no support greater than Chicago sports fans. 

When: *Hopefully through January
Where: 1410 Museum Campus Dr, Chicago, IL 60605

For more information

 
 
 
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Open House Chicago on October 19th - 20th

There are so many iconic architectural treasures that are closed off to the public, so now's your chance to see them legally. For one weekend every fall, the Chicago Architecture Center opens their doors to give you a behind-the-scenes look at some of the city's greatest spaces like mansions, sacred spaces, theaters, private clubs, hotels, and secret rooms - all for the price of, free!

When: October 19th - 20th
Where: Over 350 sites to explore. 

For more information.

 
 
 
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Take a Tour of Revolution Brewery

If you're getting sick of the pumpkin spiced movement (impossible) then get yourself a glass of Oktoberfest at Revolution. This Chicago brewery has made a name for itself in a very short period of time, becoming the 50th largest brewery in the country! They are true innovators of the craft beer scene, so cozy up with a group of friends and hit their brewpub.

When: Daily
Where: 2323 N Milwaukee Ave, Chicago, IL 60647

For more information.

 
 
 
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Run the Hot Chocolate 15K/5K on November 3rd 

You had us at hot chocolate. Whether you're running off post-Halloween candy or simply haven't had enough - this races brings together runners and chocolate lovers, alike. 

When: November 3rd
Where: Grant Park at 337 E Randolph St, Chicago, IL 60601

For more information

(Cover image courtesy of Todd R Photo) 

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