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

The Ultimate Chicago Fall Bucket List

Author Pic By Chicago Bucket List

Let the pumpkin spice rain down on us! πŸŽƒ

Published October 07, 2020

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)! 

Stroll Through Millennium Park 

The park takes on a colorful facade in the fall and is open daily, 8am to 9pm, for groups of 10 persons or fewer who practice physical distancing and wear face coverings. 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? Starting Halloween week, the drive-in will also feature socially distanced 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

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 November 1st
Where: 200 S County Line Rd, Hobart, IN 46342

For more information.


Highway Of Horror

Buckle up witches and get ready to merge onto the Highway of Horror. This haunt is set in an eerie lot in the shadows of the skyscrapers of Chicago’s iconic Loop. You'll first settle in with a drive-in movie experience that sets the narrative. Dozens of the undead, demons, zombies and more jump out and rock your car accompanied by sound effects and sprays of blood.

When: Thursday, October 15th - Sunday, November 1st 6:00PM - 10:00PM
645 W Madison St Chicago, IL 60661

For tickets and more information.

Replay's Stranger Patio

A particularly strange patio has taken over the social-distanced Replay space and it’s truly turning our worlds upside down. It’s an eleven out of 10. Each ticket includes a social distanced table for 1 hour, 2 strangely themed cocktails, a shot and countless photo ops with your favorite characters. Guests under 21 are welcome before 6PM.

Where: 2833 N Sheffield Ave, Chicago, Il 60657
When: Open Daily (hours vary)

For tickets and more information.

360 CHICAGO Tilt + Cocktail

As the weather dips and you begin looking for things to do inside, why not check 360 CHICAGO off your bucket list? Though the indoor Bar94 is temporarily closed, our Bucket Listers exclusive will get you access to 360 CHICAGO + TILT for a discounted price. Stay tuned for tickets coming soon.

Where: 875 N Michigan Ave, Chicago, IL 60611

Tickets only available here.

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

Enjoy A Coffee Tour And Tasting At Starbucks Roastery 

Loving pumpkin spice lattes might get you called out for being a basic witch. Yet that’s a risk we’re happy to take if it means we can savor in the cinnamon delight of a warm PSL. Beyond seasonal treats, for anyone searching for the full Roastery adventure, experiential tours are available every weekday for booking. Plus, you can even partake in coffee tastings and espresso martini tastings. I’ll *cin, cin* to that πŸ₯‚

When: Everyday from 8:00AM-9:00PM
Where: 646 N Michigan Ave, Chicago, IL 60611

For more information.

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.

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

The Friends Experience

Have you ever found yourself reminiscing about the great times you spent watching FRIENDS™? Well grab your closest pals and check out a new exhibit, "The FRIENDS™ Experience" to be immersed in the show like never before! Borrow one of Chandler’s sweaters because FRIENDS™ is officially blowing into the Windy City this October. 

When: October 1, 2020 - January 3, 2021
Where: The Shops at North Bridge on the Magnificent Mile at 540 N. Michigan Avenue

For tickets and more information. 

JoJo's Pumpkin Patch

JoJo's Pumpkin Patch is set in the heart of River North! Featuring their famous Pumpkin Patch Shake, gourmet caramel apples, BIGGIE Salted Caramel Hot Chocolate, spiked ciders and more. 

When: 11am - 11pm daily until November 1st 
Where: 23 W Hubbard St, Chicago, IL 60654

For more information.

Fall at Lincoln Park Zoo

To prioritize safety there will be no Fall Fest this year, but plenty of unbe-‘leaf’-able fun for the whole family from October 1-November 1. Simply make your free reservation to visit the zoo this fall to stroll the one-way trail and cherish the fall ambiance without the crowds. 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: Friday through Sundays at 10AM - 4PM.
Where: 2001 N Clark St, Chicago, IL 60614

For more information.


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Do we really need an explanation? 

When: Chicagoans have 3 ways to vote this fall

  1. Early In-Person (Sep 24- Nov 2)
  2. By Mail
  3. Election Day (Nov 3)



(Cover image courtesy of Todd R Photo) 

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