Slideshow: Staff Picks: The Best Dessert in Chicago

Brioche Doughnuts with Hot Fudge at Mindy's Hot Chocolate
Brioche Doughnuts with Hot Fudge at Mindy's Hot Chocolate

"I've only ever had dessert at Hot Chocolate, and I don't care if I ever try their regular food (which I've heard is also great). That's because these donuts have spoiled me. I had them on my first visit, and dipping the fluffy doughnuts covered in sugar into that hot fudge, and then chasing it with a shot of the heavily coated caramel corn, shows you in one bite why Hot Chocolate is known for its desserts. Molly Durham

Drunkin' Donuts with Jamo Soft Serve at Boiler Room
Drunkin' Donuts with Jamo Soft Serve at Boiler Room

"Dessert seems like a splurge to me. Unless my wife and I are on a date or I'm checking out a spot for SE, I'm unlikely to order it. But I'll gladly make an exception for the Drunkin' Donuts with Jamo Soft Serve at Boiler Room. It's a throwback to the childhood cones that ended most meals at my hometown Pizza Hut. Plus, it's either legitimately boozy, or I'm just good at fooling myself into having a buzz." Joe Roy

Pie at Hoosier Mama Pie Co.
Pie at Hoosier Mama Pie Co.

"Doesn't matter what kind, I love all the pies at Hoosier Mama Pie Co. But since I have to make a choice, perhaps I'll give the edge to the fruit pies, because the fillings manage to hover in that magic realm, where they are neither overly sloppy or so loaded with cornstarch they won't budge at all. Oh, but the Hoosier cream pie (pictured above) is kind of flawless—light and yet with a satisfyingly caramelized profile. Of course, just about any filling would be good on Hoosier Mama's flaky and buttery crust. So yeah... all the pies.Nick Kindelsperger

Homemade Banana Pudding at BJ's Market
Homemade Banana Pudding at BJ's Market

"My sweet tooth seems to come with warm weather. I grew up on Italian Ice, not ice cream, and will always have a special place for that. But when I want something hearty when the cool air rolls around it's BJ's Market on Stoney Island for some of their signature homemade banana pudding that comes to my mind. It's rich, it's creamy, and it sings inside your mouth. Plus, it's the perfect dessert after chowing down some mustard fried catfish. Titus Ruscitti

Pumpkin Napoleon at Mindy's Hot Chocolate
Pumpkin Napoleon at Mindy's Hot Chocolate

"Mindy's Hot Chocolate offers some of the best desserts I've ever tasted. It's a cozy, candlelit place that offers lunch and dinner, but also boasts award-winning desserts. Since the autumn chill has finally arrived, the best way to celebrate the season is with their pumpkin napoleon ($12). It's not the kind of napoleon you're probably thinking of, with layers of wafers and custard, but their spin makes it all the more special. You're given a decent portion of their local spiced pumpkin cheesecake that sits on top of a graham cracker. They add toasted marshmallows on top of the cheesecake that have that crispy burnt shell on the outside (the way I like mine done). Hot buttered rum is brûléed on top, and candied cranberry and rum raisin ice cream comes on the side. This combination of spiced pumpkin, warm rum, ice cream, and gooey marshmallows makes this dessert a treat to ring in the fall. Chelsea Ross

The Chocolate Peanut Butter Vegan Shake at the Chicago Diner
The Chocolate Peanut Butter Vegan Shake at the Chicago Diner

[Photograph: Lindsey Howald Patton]

"This is one of those rare desserts that makes even those who roll their eyes at the word 'vegan' wonder why we bother with dairy. Most folks—including me—claim it's better than a 'real' shake. The strawberry flavor is perfection and people rave about the cookie dough, but I'm a fan of this one, which tastes like a dressed-up Reese's Cup. The base is a small-batch organic soy ice cream called Temptation, made here in Chicago. It's loosened up with soy milk and given a big spoonful of peanut butter for that classic sweet n' salty combination of flavors, and then topped with vegan whipped cream and a sprinkling of peanuts. Stick a straw in it and welcome: you have officially arrived in vegan heaven. Lindsey Howald Patton

Drinking Chocolate at Katherine Anne Confections
Drinking Chocolate at Katherine Anne Confections

"There is a void deep within me that only deep, rich chocolate can fill. Preferably the kind of chocolate found at Katherine Anne Confections, the closest thing Chicago has to a Willy Wonka-type wonderland. Katherine Duncan's cozy cafe is a playground for my chocoholic senses, and each trip has me salivating like Augustus Gloop by the chocolate river. Along with her exotic truffle flavors (ginger-passion fruit was a recent standout as it singed my tongue in the most pleasant way), I obsess over the warm drinking chocolates. Decadent and thick and poured in hearty portions with a couple housemade marshmallows melting on top, each serving is comparable to drinking a cake. And it hurts so good. The shop sports a whole menu of drinking chocolates, but my favorites are always her seasonal specials. Pumpkin drinking chocolate is the single greatest thing about cold weather in Chicago.Matt Kirouac

Cupcake at Sweet Mandy B's
Cupcake at Sweet Mandy B's

"The frosting is the best I've ever had in the city and I've never been disappointed in any cupcake flavor, though I'm partial to the classic yellow cake with vanilla frosting. The cupcake itself is moist, yet light. They stick to classic cupcakes flavors and always deliver." Tessa McLean

Festa di Santa Lucia Crema at The Purple Pig
Festa di Santa Lucia Crema at The Purple Pig

A picture of the dessert was hard to track down, but here's a reminder that you should have a few glasses of wine before the final course comes around. [Photograph: Nick Kindelsperger]

"I've never cared for sweetness alone—even as a kid my favorite Baskin-Robbins flavor was tart Daiquiri Ice, which always got a raised eyebrow as an 8-year-old ordered Hemingway's favorite cocktail. So I'm happy with desserts that just skirt the edge of sweetness, the way many European pastries do. I think the one dessert that came closest to my ideal was at The Purple Pig, something called Festa di Santa Lucia Crema, ricotta creamy like yogurt, dotted with chewy little nubbins of farro and with chocolate sauce to be poured over. Even with the rich dark chocolate, the farro and ricotta seem as plain and working-class as a peasant in his only suit, giving this dessert a proletarian heartiness far removed from effete French pastries. It's off the menu right now, but something called Santa Lucia has to come back by Christmas, right? Mike Gebert