Think Outside the Pie With This Pumpkin Bucket List at Local Restaurants

Everyone loves a good pumpkin pie. It's quintessential fall comfort at its best, and rightfully so. The period of October into November is the acme of Dining Chicago's pumpkin season, with a pumpkin version of seemingly every food and drink on a menu somewhere. Pumpkin-flavored fatigue, anyone? Keep things fresh with this guide to some of Chicago's most crafty pumpkin creations, from a pumpkin tiramisu to pumpkin spice milk, pumpkin cocktails, pumpkin sticky buns, and lots more.

"Pumpkin spice" are the buzz words of all. Whisper them softly and you'll be met with a horde of hungry/thirsty pumpkin fiends looking to satiate their rampant addiction. Usually this entails a latte, but Three Aces restaurant is doing something special with pumpkin spice. Check out their pumpkin spice tiramisu. The ideal blend of Three Aces' Italian roots with contemporary verve, the dessert features ladyfingers soaked in a blend of Rumchata and Dark Matter coffee, layered with pumpkin mascarone, and adorned with crumbled amaretti and cocoa nibs. Check your lattes at the door.

Pumpkin spice tiramisu at Three Aces
(Pumpkin spice tiramisu at Three Aces)

If you're still thirsty for pumpkin you can drink, look no further than Katherine Anne Confections bakery. The triumphant seasonal return of the pumpkin drinking chocolate is upon us, and it is other-worldly. The hearty beverage is two-tone, with one flavor for each side of the hefty mug. On one side you've got white pumpkin hot chocolate with cayenne, ginger, and balsamic, while the other boasts dark pumpkin hot chocolate with bourbon, brown sugar, and maple. This stuff is insanely rich, so proceed with caution, share with a friend, or fill out a waiver. Consuming the whole thing feels like drinking an entire pumpkin pie, but it's worth it. Drinking chocolate comes topped with two pillowy, saccharine marshmallows in the flavor of your choice. If they're available, I'd recommend cranberry.

Another great pumpkin quaff this season is the invigorating pumpkin spice milk at Doc B's Fresh Kitchen, the Gold Coast newbie with a wholesome heart. The restaurant is the only brick-and-mortar spot to offer juices and juice-adjacent beverages from JuiceRx, a company specializing in fresh, locally sourced ingredients that are unpasteurized, vegan, and organic. There are interesting drinks like the Liquid Lipo, said to cleanse fat cells and boost the immune system, but the one that really stands out this time of year is the pumpkin spice milk. The fall-centric drink features filtered water, carrot, sprouted pumpkin seeds, dates, pumpkin spices, Tahitian vanilla bean, Himalayan sea salt, and Stevia. Its nourishing benefits include the ability to flush toxins, sharpen eyesight, and "make taste buds happy," which is a given.

Pumpkin sticky bun at Floriole
(Pumpkin sticky bun at Floriole Cafe & Bakery)

Contender for pumpkin pie's greatest competition is the pumpkin sticky bun at Floriole Cafe & Bakery. The gooey, doughy goodness of a classic sticky bun gets dolled up for fall with the inclusion of pumpkin puree. The sticky pastry is topped off with a schmear of cream cheese frosting, making it impossible to resist its allure. And you shouldn't try.

Who says ice cream is just for the warmer months? Unfriend that person and get thee to Scooter's Frozen Custard for their seasonal standby, the pumpkin pie concrete. This adorable shop in West Lakeview treads in decadent frozen custard, thicker and creamier than ice cream, and handily mixed with add-ons to create intense desserts called concretes. Why is that? Because it's so thick you can practically construct a house with it. Forget about conquering this thing with a straw. It's mighty indulgent, made by blending frozen custard with a slice of pumpkin pie, capped with a corona of whipped cream, and a sprinkling of graham cracker crumbs. Oof.

The Horseman at Rebar
(The Horseman at Rebar)

At this point you're probably all sugared out. Here to prove that pumpkin isn't all pie and pastries, Takashi is serving up pumpkin risotto with chanterelle mushrooms, roasted pumpkin seeds, and pumpkin oil. It's pumpkin-tastic! At mk The Restaurant, cumin-scented pumpkin and toasted pumpkin seeds bolster a dish of pan-seared Maine diver scallops with braised Napa cabbage. And at The Gage, roasted pumpkin soup comes with smoked duck, toasted pumpkin seeds, housemade crème fraîche, and basil oil.

Pumpkin potables get intoxicating at places like The Boarding House restaurant. The River North restaurant is a veritable wine temple, but its cocktails should not be overlooked. Such as The Great Pumpkin, a medley of rye whiskey, Grand Marnier, lime juice, star anise, and pumpkin puree. The Pumpkin Splash at Lush Wine and Spirits is not your average vodka martini, accented with pumpkin puree, Koval Ginger Liqueur, and Fentimans ginger beer. Pumpkin ice cubes are a thing, and they're on the menu at Rebar. The decadent cocktail bar uses pumpkin cubes to spice up and cool down The Horseman, featuring house-aged cinnamon apple Irish whiskey and hand-crafted bitters.