Matt Kirouac

Judging by the chill in the air and the inescapable onset of the impending holiday brouhaha, it's clear we are deep in the throes of fall. For better or worse. Mostly for the better when you consider the dining and drinking options the season entails, and nothing quite captures the essence of fall dining quite like apples and pumpkins.

Toni Patisserie & Cafe (65 E. Washington St.)

Matt Kirouac

Pumpkins and apples take the stage for two glorious, illustrious desserts at Toni Patisserie & Cafe in the Loop. Thinking well outside the bounds of typical fall pies, the fall menu now includes pumpkin mascarpone roulade with cinnamon glaze and candied pumpkin seeds. Apple-wise, there's apple-cinnamon bread pudding, apple slices royale, and taffy apple macarons.

Additionally, the patisserie is running a month-long Halloween-themed macaron special inspired by "Trick or Treat" candy. These fun little morsels include candy corn, Almond Joy, Red Hots, Heath Bar, and Grape Pop Rocks.


Girl & the Goat (809 W. Randolph St.)

Considering Girl & the Goat's proclivity for shareable plates, it's easy to make a full-fledged meal out of apple and pumpkin creations this season. And true to form, chef Stephanie Izard dazzles with her innate knack for innovation. Think celery root and cheddar dumplings with apples, maitake, and miso-mushroom broth; pan-seared diver sea scallops with Cubano pork, apple mojo, and pepper-raisin relish; and Mt. Lasen trout with pumpkin brandade, fried Brussels sprouts, candied pecans, and pomegranate.


Perennial Virant (1800 N. Lincoln Ave.)

Two words for you: pumpkin beignets. Now allow me to elucidate a bit. Find them at Perennial Virant this season, where chef de cuisine Ed Sura handily displays the restaurant's penchant for seasonality and preserves via preserved pumpkin beignets with Concord grape, maple-sherry aioli, arugula, and Little Darling cheese.


TWO (1132 W. Grand Ave.)

Matt Kirouac

So many apples are pouring off the menu at TWO, the only thing missing is Sir Isaac Newton's head. Chef Tom Van Lente is currently serving up a mixed greens salad with housemade ricotta fritters, house-smoked Hampshire bacon, Honeycrisp apples, cucumbers, watermelon radishes, and black pepper-herb vinaigrette; smoked Berkshire pork shoulder on sweet potato puree with apple-radish-arugula salad; and smoked pork loin carpaccio with pork demi-glace, bacon-apple-radish salad and flaked sea salt. And for dessert, chef de cuisine Kevin Cuddihee takes the lead on a Honeycrisp apple pie with bourbon-caramel glazed apples in a bacon fat pie crust topped with housemade cinnamon ice cream.


LUXBAR (18 E. Bellevue Pl.)

The new seasonal cocktail list at LUXBAR has "fall" drizzled all over it. Inspired by fall's most prominent spices, consider double-fisting the Allspice cocktail and the Nutmeg to maximize your seasonal buzz. The former is made with Old Forester bourbon, Bitter Truth Pimento Dram, pumpkin puree, fresh lime, simple syrup, and angostura bitters; while the latter contains Castrede Armagnac, Lazzaroni Amaretto, apple juice, egg white, simple syrup, and angostura bitters.


More (1 E. Delaware Pl.)

Fall takes cupcake form at More, one of the city's most deliciously envelope-pushing boutique cupcake shops. Start with the pumpkin cinnamon cream cheese cupcake made with pumpkin cake, cinnamon cream cheese frosting and pepita brittle, then chase it with a pumpkin cheesecake cupcake made with a ginger crust and pumpkin cheesecake swirled with pecan praline buttercream. Don't forget about apples, either. The apple caramel cream cheese cupcake takes a back seat to no pumpkin, featuring an apple cake with caramel cream cheese frosting and walnut brittle.


Gemini Bistro (2075 N. Lincoln Ave.)

Fall desserts are the best desserts; supremely comforting and heartwarming to the core. Case in point, the latest dessert roster at Gemini Bistro, where caramel apple crisp is adjoined by cinnamon streusel and praline gelato, and pumpkin crème brûlée comes outfitted with spiced custard and cranberry hazelnut biscotti.


Travelle (330 N. Wabash Ave.)

Matt Kirouac

The perfect dinner pairing this season may very well be found at Travelle. Here, the slick Mediterranean-inspired restaurant is serving pumpkin seed-crusted striped bass for dinner, along with Pumpkin Mules to drink, made with pumpkin syrup, bourbon, lemon juice, cinnamon, and sage.


Blackbird (619 W. Randolph St.)

Another killer pairing skews sweet at Blackbird. The Lake Effect cocktail is an apple brandy libation filled out with orgeat and Luxardo Amaro Abano, rinsed with smokey laphroaig. Then for dessert, there's a gooey brown butter cake served with liquid pumpkin pie, bourbon barrel ice cream, smoked pecans, and Steen's cane syrup.


Nana (3267 S. Halsted St.)

Pumpkins and apples are all over the menus at Nana, from breakfast and dessert to cocktails galore. In the a.m., get your fill of pumpkin cheesecake-stuffed French toast with bourbon syrup. Then at night, finish your dinner with pumpkin bread pudding for dessert.

To drink, try the pumpkin butter rum made with fresh pumpkin butter, dark rum, allspice liqueur, fresh whipped cream, and nutmeg. And Nana's signature Appleseed Contract cocktail is always a good bet, featuring housemade apple butter, Old Overholt Rye whiskey, lemon juice, angostura bitters, and ginger beer.


Mindy's Hot Chocolate (1747 N. Damen Ave.)

When hankering for a seasonal dessert finale, look no further than Hot Chocolate, Chicago's quintessential dessert destination. James Beard award-winner Mindy Segal continues to wow with her latest crop of creations, an apple dessert made with warm apple chess tart, Calvados ice cream, sour cream, caramel tuile, and caramel cream; and a pumpkin layer cake comprised of pumpkin cheesecake buttercream, cranberry sorbet, pecan candy, spiced pepitas, butter rum, and cranberry jam.

Photos: Toni Patisserie & Cafe, TWO, Travelle