Seasonal & Holidays

The Ultimate Fall Bucket List, According To Chicago Tastemakers

Chicago's top chefs, mixologists and bloggers weigh in on the best local spots to celebrate autumn.

Teeming with cozy vibes, crisp weather and spooky holidays, fall is one of the best times of year. And we can't help but embrace the season's distinct character, as well as all of the pumpkin- and apple-flavored goodies it brings.

But fall isn't going to last forever, people, and with so many autumnal traditions and treats available in Chicago, it's important to determine which of them are the most deserving of your time.

That's why we've enlisted expert help to streamline our fall bucket list, making sure we've included only the best of the best destinations around the city.

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From mouthwatering seasonal bites (Hello, caramel apple bombolato!) to the most scenic foliage views, see what spots our favorite Chicago chefs, mixologists, bloggers and influencers touted as their fall favorites:


Celebrate The Season At A Fall Festival

(Image Credit: Shutterstock/ Ingeborg Knol)

According to Chef Fabio Viviani of Chicago's Siena Tavern, the best fall festival in town is Chicago Gourmet, which he participates in every year. "The festival highlights some of the best chefs in the country, and I am just honored to be part of it," explains Viviani.

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Take Advantage Of Pumpkin Spice Season

Pumpkin Pie Le Stan from Stan's Donuts (Image Credit: Amanda Topper)


For Amanda Topper, blogger of The Ghost Guest, the Pumpkin Pie Le Stan from Stan's Donuts takes the cake! "It’s a croissant dough doughnut filled with real pumpkin pie filling and topped with pumpkin glaze," explains Topper.

While cocktail blogger Jason Pirock of Eat, Drink, And Bloody Mary isn't a huge pumpkin fan, he does enjoy the maple + maca + pecan latte from Oromo Cafe.


Enjoy Some Apple Flavored Food

Avocado Chip and Pumpkin Pecan flavors from BomboBar (Image Credit: BomboBar)

"When it comes to apples, my favorite drink is the Rhine Hall Distillery la Normande American Style Pommeau," says Julia Momose, mixologist behind West Loop restaurant Oriole. Momose also plans to serve some pommeau at Kumiko, the Japanese-inspired bar she is opening later this fall.

Viviani highlights his own Chicago-based doughnut and gelato shop, BomboBar, for their fall flavor caramel apple bombolato. "It will be everything you expect including gelato, bomboloni and of course, the apple and caramel flavors," explains Viviani. Some other enticing fall favors include avocado chip and pumpkin pecan.

Bang Bang Pie Shop also made more than one tastemaker's list for its famous pumpkin and apple cider pies.


Visit An Apple Orchard

(Image Credit: Rick Uldricks/Patch)

Topper says County Line Orchard is the ultimate spot for fall festivities. "You can pick apples and pumpkins, get lost in the corn maze and enjoy plenty of seasonal treats including baked fresh apple cider doughnuts," she says.

Pirock prefers a place a little closer to home, including Kuipers Family Farm, where you can participate in fun fall activities like pumpkin picking and petting zoos.


Take In The Fall Foliage

(Image Credit: Sammy Faze Photography)

It's no secret that Chicago is overflowing with stunning views. Momose, who lives along the Green Line, states that one of her favorite views is actually from the train. She highlights the fact that as the foliage sheds, it reveals more of Chicago's cityscape.

She also enjoys taking in the city's best views aboard the Architecture Boat Tours along the Chicago River. "This is a great chance to bundle up and sip on some hot cider while taking in the beautiful city from the water," says Momose.


Take A Trip To A Brewery

(Image Credit: Shutterstock)

Both Momose and Topper both named Moody Tongue Brewing Company as their favorite spot to grab a brew in the city. "Cozy up next to their fireplace, order a slice of their famous German chocolate cake, and try a flight of their creative beers," says Topper. On the other hand, Pirock insists Revolution is one of the best breweries in town.


Indulge In A Seasonal Cocktail

No. 5 cocktail from Siena Tavern (Image Credit: Siena Tavern)

"Siena Tavern has this cocktail named No. 5, and it is one of my favorites to drink this time of year," says Viviani. The signature cocktail is crafted with allspice dram, ginger apple cider, cinnamon, clove, Averna Amaro, bitters, lemon and just the right amount of Maker's Mark.


Watch The Big Game

(Image Credit: Shutterstock)

It wouldn't be fall without some football! "Whenever I have some downtime and get to catch a football game, you can always find me at Public House in River North," says Viviani. "The bar has a 30-foot wall of televisions and a ton of other viewing options throughout the bar."


Stage An Autumnal Photo Shoot

(Image Credit: Sammy Faze Photography)

When it comes to the most picturesque spot in the city, there might be too many to name (but we will certainly try). Momose points out Garfield Park Conservatory and the backyard patio of Best Intentions as her favorite spots to snap a pic, while Pirock and Topper suggest the Lincoln Park neighborhood.

"Taking a stroll through Lincoln Park near the Lincoln Park Zoo and North Pond is a great idea any time of year, but even prettier during fall months," explains Topper. "You can catch views of the changing leaves in front of the Chicago skyline."


See More From Our Chicago Tastemakers:


Main Image: Pumpkin Pie Le Stan from Stan's Donuts (Image Credit: Amanda Topper)

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