Bucket Listers

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Published January 19, 2023

Chicago's Ultimate 2022 Fall Bucket List

Make your autumn in Chicago legendary. 🍁

by Chicago Bucket List


Nothing beats fall in Chicago. The city transforms with a rainbow of foliage and lots of unique activities. Whether your idea of the perfect fall day is picking apples, making new friends, wandering through a corn maze, or watching a scary movie in the park, we’ve got you covered. Read on for our 2022 Ultimate Chicago Fall Bucket List!

Taste of Fulton Market | September 29

Enjoy some killer food, and fun interactive activities, while raising money for a great cause at Taste of Fulton Market on September 29th. Admission gets you samples of food from some of Chi Town’s best eateries, like The Publican, Carnivale, Rose Mary, BLVD, Gus's Fried Chicken, Marvin's Food and Fuel, Bar Takito, KOMO, Blind Barber, and more.

Where: Morgan's on Fulton 950 W Fulton St, Chicago, IL
For more information on Taste of Fulton Market.


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Oktoberfest Beer Tasting | September 23-24

Grab your lederhosen and your stein—Oktoberfest is back at St. Alphonsus! Admission gets you 15 tastings of different craft brews from near and far. Maybe you’ll find the perfect six-pack to bring to Thanksgiving dinner!

Where: St. Alphonsus Downstairs Beer Hall: 1429 W Wellington Ave., Chicago, IL
For more information on Oktoberfest Beer Tasting.

Lincoln Square Annual Apple Fest | October 1-2

Enjoy all the apple-y goodness you can take at the Lincoln Square Ravenswood Chamber of Commerce's 35th Annual Apple Fest! The Ravenswood community will usher in the fall season on October 1st and 2nd this year. You won’t wanna miss the family fun! 

Where: Lincoln Avenue between Lawrence and Wilson, Chicago, IL
For more information on Apple Fest.

WingOut Chicago | October 1-2

Whether you’re a football fan or not, everyone can agree that chicken wings are the top snack of the season. Have all the fun of a tailgate with all-you-can-eat wings at WingOut Chicago on October 1st and 2nd! 

Where: St Michael Catholic Church in Old Town: 1633 N Cleveland Ave, Chicago, IL
For more information on WingOut.

Chicago Marathon | October 9

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, 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! 

Where: The race starts and finishes at Grant Park.
For more information on the Chicago Marathon.

Lincoln Park Wine Fest | October 8-9

For the seventh 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 worldwide varieties. Vino, Wein, Vin, and did we say sangria?

Where: Jonquil Park: 1001 W Wrightwood Ave., Chicago, IL
For more information on LP Wine Fest.

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

Take in the crisp fall air while wandering down the trails lined with thousands of hand-carved pumpkins. The only thing that could make it better is a hot cup of spiced cider!

Where: 1000 Lake Cook Rd, Glencoe, IL
For more information on Night of 1,000 Jack-O-Lanterns.

Make Your Own Candle

Whether you need a new pumpkin spice candle for your office or want to bring the perfect homemade hostess gift to Thanksgiving dinner, this candle-making class is the perfect place to learn a new skill and leave with a keepsake you’ll be proud of. 

Where: Chicago Candle Co. 1100 W Cermak Rd #419, Chicago, IL
For more information on Chicago Candle Co.

DIY Charcuterie Board Class

Spend a chilly fall day learning how to make an Instagrammable charcuterie board just in time for Thanksgiving. Your ticket includes everything you need for the perfect charcuterie board: dried fruits, fresh nuts, cheese, and meat, as well as one red or white wine pairing and a complimentary glass of prosecco at the end of the class!

Where: Dom's Kitchen and Market: 2730 N Halsted St, Chicago, IL
For more information on DIY Charcuterie Board Class.

BOO-zy Bowling Social at The Pink Squirrel

Who's up for a night of Halloween-themed bowling? Whether you’re looking for new pals for Friendsgiving or a new boo before the holidays, you might just make some connections at this BOO-zy Bowling Social! Have some drinks, chat it up, and get ready to get cozy with someone new. 

Where: The Pink Squirrel, 2414 Milwaukee Ave, Chicago, IL
For more information on the Boozy Bowling Social.

Open House Chicago | October 15-16

Get up close and personal with some of Chicago’s oldest buildings and neighborhoods. Chicago Architecture Center’s annual open house event allows self-guided history and architecture tours throughout Chicago all October long. We’re not saying these old buildings are haunted… but we aren’t saying they aren’t, either. 

Where: Various locations
For more information on Open House Chicago.

See Fall Foliage at the Morton Arboretum

The Morton Arboretum publishes a weekly fall color report every Friday, so you won’t miss the peak views of the season! Wander through the maple and oak collections, traipse across the Schulenberg Prairie, or stroll along the Meadow Lake Trail. No matter what you choose, the foliage is sure to be epic.  

Where: 4100 Illinois Route 53, Lisle, IL
For more information on Morton Arboretum.

Immersive King Tut

Follow Tutankhamun on his journey through the underworld this Halloween season at the brand new Immersive King Tut exhibit. You might even want to bring your mummy along!

Where: Lighthouse ArtSpace Chicago: 108 W Germania Pl, Chicago, IL
For more information on Immersive King Tut.

Speakeasy Magic Show

Get into the Halloween spirit with some mind-blowing magic from magician Mike O’Donnell at Lulu’s. Admission to one of the weekly events even includes a free drink! 

Where: Storyville: 712 N Clark St, Chicago, IL
For more information on Speakeasy Magic Show.

Wine, Dine and S'mores Day Trip

What could be better than getting out in the crisp fall air surrounded by foliage? Enjoy wine, food, and s’mores during a fun day trip at luxury glamping site, Camp Aramoni! The best part? You get all the fun of a camping trip, but you get to sleep in the comfort of your own bed at the end of the day. 

Where: Pickup at 3317 W Fullerton Ave, Chicago, IL
For more information on Wine, Dine, S'mores Day Trip.

See the Fall Colors at Promontory Point

Promontory Point might just be one of the most beautiful places to take in the fall foliage in Chicago. Watch the trees reflect on the waterfront while taking a stroll around the bird sanctuary. It doesn’t get more autumn than that! 

Where: 5491 S. Jean-Baptiste Pointe DuSable Lake Shore Drive, Chicago, IL
For more information on Promontory Point.

ChiTown Drive-In Movies

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 encouraged.  

Where: 2343 S Throop St, Chicago, IL
For more information on ChiTown Drive-In Movies.

BOO-zy Pumpkin Carving

This freestyle, collaborative class lets you carve and paint pumpkins and drink unlimited wine while you do it. Pumpkins, paints, and tools are included, and a la carte food options are available as well. 

Where: Electric Garden: 324 S Racine Ave, Chicago
For more information on BOO-zy Pumpkin Carving.

The Richardson Corn Maze

Betcha didn't know the largest corn maze in the world is in Illinois, did ya? 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 to 10 miles of trails winding through 28 acres of live corn, you’re in for a challenge and a treat!

Where: 909 English Prairie Rd, Spring Grove, IL
For more information on The Richardson Corn Maze.

Halloween Origami Fold & Sip BYOB

At this event, Chicago's 2d restaurant will be transformed with Halloween-colored lights and decor, and a skilled origami teacher will teach a variety of Halloween-themed origami. Try your hand at the art of folding paper and take home a witch, pumpkin, ghost, and other paper Halloween decorations. This event is BYOB, and tickets include a witchcraft chicken sandwich with bloody fries, lemonade, and a mochi donut.

Where: 2d Restuarant: 3155 N Halsted St, Chicago, IL
For more information on Halloween Origami Fold & Sip BYOB.

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 (yes, 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. 

Where: 200 S County Line Rd, Hobart, IN
For more information on County Line Orchard.

Aster Hall

As the weather starts to cool down, Aster Hall has plenty of indoor activities to keep the party going. Practice your long game in the TopGolf Swing Suite, grab a quick bite in the food hall, or get some remote work done in their chic Bar and Study. 

Where: 900 N Michigan Ave Level 5, Chicago, IL
For more information on Aster Hall.

Throw Back Movie Club’s 30 Days of Halloween

Get your costumes ready, because Throw Back Movie Club is going spooky for their 30 days of Halloween! Catch classic spooky films like Hocus Pocus and Scream, and indulge in treats that go along with the theme. Oh, and don’t forget everyone’s favorite “take a shot every time someone…” game, with complimentary shots!

Where: Electric Garden: 324 S Racine Ave, Chicago, IL
For more information on Throw Back Movie Club’s 30 Days of Halloween.

Goebberts Farm

Trick or treat yourself to Goebbert’s Pumpkin Patch & Apple Orchard. Their fall festival is every day until Halloween, offering a full day of family-friendly activities that are sure to delight kids and grown-ups alike. The general admission fee includes almost all of the activities on the farm. 

Where: 2W813 Reinking Road Pingree Grove, IL
For more information on Goebberts Farm.

Take a Day Trip

There's so much to love in Chicago in the fall, that sometimes we forget there's a whole world of lakes, waterfalls, forests, and more just a short drive away. Fall is the perfect season to pack up the car, and hit the road—and experience some prime fall foliage along the way. From art and beaches in Saugatuck to wine tastings and boutique shopping in Cedarburg, there are plenty of options for anyone wanting a mini escape from the city.

For more information on day trips from Chicago.

Pumpkin Painting at JoJo's Pumpkin Patch

Gather the family, friend group, or the office softball team, and head to JoJo’s Pumpkin Patch for food and fall festivities. Pick a pumpkin from the patch and paint it to your heart’s desire, then order from a menu that includes smash burgers, pot pies, caramel apples, pumpkin and apple pies, and spiked hot cocoa. Not to mention a full bar with signature cocktails and JoJo’s famous pumpkin patch shake.

Where: River North,  23 W Hubbard St
For more information on Pumpkin Painting at JoJo’s Pumpkin Patch.