Chicago's Coziest Hot Cocoas

The best, most delicious way to ward off frigid winter temps in Chicago is with a rich-as-cake drinkable dessert that is hot chocolate. Fortunately, Chicago is a city brimming with decadent hot chocolates in many forms, from the classic to the boozy dessert. Here are some of the best hot chocolates in Chicago you need in your lives: 


Katherine Anne Confections
Hot chocolate perfection at Katherine Anne Confections


When it comes to hot chocolate, it doesn’t get any more decadent than the incomparable drinking chocolate at Katherine Anne Confections. This stuff is intense, more akin to a melted chocolate bar than your typical cocoa. As thick and hefty as it is, you’ll have a hard time restraining yourself from gulping down an entire cup, especially when options like pumpkin hot chocolate and white chocolate-chai hot chocolate are on hand. Each one comes outfitted with a duo of pillowy housemade marshmallows in flavors like peppermint and cinnamon sugar. There’s even a slightly meta hot chocolate marshmallow made with cayenne, habanero, and cocoa powder.


Another place that should come as no surprise is the aptly dubbed HotChocolate. Bucktown's iconic, enduring dessert destination peddles an incredible roster of flavors such as chai, Mexican hot chocolate, old fashioned made with milk chocolate, a hint of caramel, and milk chocolate cocoa nib whipped ganache, and black and tan made with hot fudge. They're all served with housemade marshmallows, available for dine-in dessert or in to-go cups. I recently took one to-go and walked along the nearby 606 Trail and it was perfect. 


Speaking of Mexican hot chocolate, options abound in Pilsen. In addition to the myriad champurrado carts parked along 18th Street, one of the best versions can be sipped at La Catrina, a massive Day of the Dead-looking cafe with tons of Frida artwork and imagery scattered throughout. Needless to say, a nice setting to drink one of their signature hot chocolates, like the Dirty Abuelita, which is cayenne- and cinnamon-spiced Mexican hot chocolate with a splash of espresso. 

Cindy's cocoa goodness


For Cindy's first winter in operation, the rooftop restaurant at the Chicago Athletic Association hotel is going big. And by that I mean serving three different booze-filled hot chocolates as part of the dessert menu. And these things are huge, served in massive mugs and filled to the absolute brim with creamy goodness. The Classic contains Madagascar vanilla, Guayaquil chocolate, vanilla marshmallows, and Tuaca, a vanilla- and citrus-scented Italian liqueur; the Cinnamon Maple features Blis maple syrup, Guayaquil chocolate, cayenne, cinnamon, chicory marshmallows, and Ancho Reyes chile liqueur; and the Nutella Framboise is made with Nutella, Guayaquil chocolate, raspberry marshmallows, and St. George Raspberry liqueur. All hot chocolates can be ordered with or without the alcohol component. 


Another notable newcomer this winter is Spinning J. The adorably nostalgic Humboldt Park bakeshop has one of the best versions of hot chocolate in the city this season. The best part about it is how deliciously simple and straightforward it is, infused with housemade hot fudge for the chocolate component. This crucial element enriches and thickens the cocoa simultaneously, making for one mighty memorable cup of rejuvenation. 



For those who want to bring quality hot chocolate home, Southport Grocery & Cafe has your back. The cafe’s housemade hot chocolate mix is the perfect pantry provision for winter, featuring an aromatic mix of sugar and cocoa powder. Don't forget to grab a pack of housemade vanilla marshmallows while you’re at it. 

Using a rigorous bean-to-cup program, XOCO sets itself apart with its peerless hot chocolate menu. Using cacao beans fresh from Tabasco, they're roasted, ground into a paste, chilled, and then added to steamed milk (or water) and sugar for made-to-order creations. Try it in one of XOCO's many iterations, from the Aztec made with water, chile, and allspice to the Mexico City Thick, which is more like a champurrado in density and richness. 

- Matt Kirouac