5 Must-Try Fall Treats To Savor This Season in Chicagoland

Savor the season with apple cider slushies, pumpkin pie milkshakes, PSL coffee flights and more seasonal flavors.

Cinnamon sugar, pumpkin spice and everything chocolate — that’s what fall treats are made of! 

When the air cools and the leaves begin to crunch, there’s nothing like a toasty pumpkin spice beverage paired with an apple cinnamon donut. Or a massive soft pretzel paired with mustard, beer cheese and an Oktoberfest brew. Plus, the spooky season is the perfect time to indulge in over-the-top sweets and all things chocolate! 

Get your family into the fall spirit by sampling some of the best fall flavors in Chicagoland. Start with a savory, Oktoberfest-style snack, then indulge with some sweet treats at eateries around the city and suburbs. Your taste buds will thank you! 

Best Fall Treats in Chicagoland 

The Pretzel at Prost!

fall treats chicago
Photo credit: Prost!

Every day is Oktoberfest at Prost! Oktoberfest beers and bites are my favorite way to kick off the season, and this German tavern in Lincoln Park is serving up a delicious fall spread for the entire family.  Start by ordering The Pretzel — a massive buttered pretzel served with mustard and warm beer cheese. Other kid-friendly options include cheese curds, schnitzel strips — think German chicken fingers!— and ham and swiss sammies. Children are allowed until 10 p.m. 

Cider Cyclone at All Seasons Orchard 

fall treats chicago
Photo credit: All Seasons Orchard

Apple cider donuts are the best-selling treat at All Seasons Orchard in Woodstock. As much as I love a fresh donut, it can be hard to pass up ice cream whenever it’s on the menu. Luckily, you can have a donut and ice cream (and even more sugary goodness) when you order the Cider Cyclone. This apple cider slushie is topped with ice cream and one of the orchard’s signature apple cider donuts, making it a delicious way to sample a variety of the orchard’s sweet treats. 

There are plenty more fall treats on the menu, too, including decadent handmade caramel apples, fresh-baked pies and sweet breads, donut sundaes and ice cream sandwiches. 

Colossal Fall Milkshakes At Creamery

Fall treats chicago
Photo credit: Creamery

Creamery is scooping up all of your favorite fall flavors this season. For an over-the-top dessert, you need to try the ice cream shop’s colossal fall milkshakes, available exclusively at the Lemont, Lombard and Sandwich locations. 

Pumpkin pie and PSL lovers will be head over heels for The Pumpkin Patch — a spiced pumpkin shake with a caramel swirl and buttercreme rim rolled in peanuts, all topped with whipped cream, candy corn and a cinnamon bun. Chocolate lovers can dig into the Cookie Graveyard, a cookies ‘n’ cream shake with nutella, Oreo crumbles, gummy worms and spooky Halloween sprinkles. And for the All-American ice cream fans, the Deep Dish Apple Pie is the treat for you — an apple pie shake with a caramel swirl, buttercreme rim, candy corn, pie pieces and a full slice of apple pie. 

We Fell in Love in October Coffee Flight at October Cafe 

Fall treats chicago
Photo credit: A’s Perfect Blend Photography

Fall fanatics will fit right in at this year-round, fall-themed cafe. Enjoy pumpkin-flavored everything, cute fall decor, and craft beverages paired with scrumptious coffee shop snacks. 

The We Fell in Love in October Fall Flight is the perfect sampling of all the shop’s fall flavors, The flight features four mini craft beverages: October Cafe’s PSL, a Maple Forest latte, a Cozy VP chai tea latte and Cuddle Weather hot cocoa.  Each flight is offered caffeinated or decaf, hot or iced, and with your choice of milk, so it’s completely customizable to your tastes and dietary restrictions. 

For the perfect pairing, try the new pumpkin toast made with local pumpkin butter, pumpkin seeds, vegan chocolate chips and sun butter. 

Fall Donuts and Drinks at Stan’s Donuts 

Fall treats chicago
Photo credit: Stan’s Donuts

  • Address: Locations throughout Chicagoland

From fresh donuts to craft beverages, Stan’s Donuts is offering all the best autumn flavors this season. Beginning Sept. 4, 2024, enjoy pumpkin old fashioneds (gluten-free options available!)  and classic or mini apple cider cake donuts

Pair your favorite specialty donut with one of Stan’s fall drinks: a pumpkin spice latte, pumpkin spice matcha or a (kid-approved!) caramel apple almond milk.


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Nikki Roberts
Nikki Roberts
Nikki Roberts is the assistant editor on the Chicago Parent team. She is always on the lookout for the coolest and trendiest new attractions, restaurants and events for Chicagoland families. Her newsletters, online family guides and exciting digital content keep families informed on all the latest happenings around town.

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