Chicago's Best Dessert Cocktails

Dessert cocktails used to be a complete afterthought on beverage menus; a treacly cavity-waiting-to-happen made with things like Godiva liqueur and other eye-roll ingredients. If that’s your thing, there are still plenty of options out there, but it’s refreshing to see dessert drinks get the craft treatment that other intricate cocktails receive. Here are several spots in Chicago stepping up their dessert cocktail game: 


The California Clipper
The California Clipper, photo by Kari Skaflen

The California Clipper: Humboldt Park’s famed California Clipper is the type of bar that offers something for everyone. With a menu the size of the Bible, cocktails are divvied into categories ranging from sparkling to stirred. One thing the venerable Clipper does particularly well is dessert mixology. With its shaved ice cocktails and ice cream drinks, the bar really set the pace for drinkable boozy desserts in Chicago. Try the tiki-inspired Pago Pago, a shaved ice cocktail splashed with rum, creme de cacao, Chartreuse and pineapple juice. Of the enriching ice cream cocktails, the Brandi Alexander is particularly delightful, made with Cognac, walnut liqueur, egg white, creme di cacao, ice cream and grated nutmeg. 

The Heavy Feather: Borrowing a page from Americana Fern Bars of ’70’s yore, Logan Square’s The Heavy Feather dives into sweet nostalgia with updated versions of dessert drinks like Brandy Alexanders, Mudslides and Grasshoppers. The key difference between The Heavy Feather and the kind of cloying milkshake-type stuff you’d find at a generic chain restaurant is that this bar pays special mind to quality ingredients and balance in flavor. 

mfk.: Some of the most astonishing dessert drinks in Chicago are found at a restaurant you probably wouldn’t expect to serve liquified Basque cake. Spanish-accented seafood Mecca mfk. works wonders with Basque cake for the dessert menu, available both in traditional solid form or blended into a boozy milkshake. Courtesy of Roger Landes, the special shake gets a splash of brandy, though even the regular cake form contains a dash of booze in the form of rhum agricole-laced pastry cream.

Another interesting dessert cocktail mfk. offers is the deceptively dubbed Coffee Cocktail. There’s actually no coffee in this one; it’s named more so for the fact that it replaces coffee as an after-dinner digestif of sorts. Inspired by a recipe from The Savoy Cocktail Book, Landes makes his with port, brandy, simple syrup, Pierre Ferrand’s dry curaçao, a whole egg and grated nutmeg. “With the meringue from the egg on top and the delightfully rich hue, the taste is just icing on the cake,” Landes says. 


Cherry Circle Room
Cherry Circle Room, photo by Clayton Hauck

Cherry Circle Room: When in Rome, do as the Romans do. Or in the case of Cherry Circle Room, when dining in an opulent restaurant reminiscent of a set piece from Mad Men, drink lavish ice cream cocktails. The restaurant tucked inside the Chicago Athletic Association hotel boasts several drinkable desserts for the adult set, including classics like a Grasshopper made with creme de menthe, cacao and vanilla ice cream. There’s also a Pink Squirrel with creme de noyaux and vanilla ice cream, and an Awful Awful, which is anything but, featuring rum, cold-brewed coffee, cacao and vanilla ice cream. 

Balena: If the classic childhood PB&J were to grow up and develop a penchant for mixology, it would be the Lambrusco Float at Balena. The Italian restaurant works wonders with nostalgia flavors in this quirky tipple, comprised of hazelnut gelato, Lambrusco and Valrhona dolce pearls. By swapping hazelnut gelato for peanut butter and sweet red wine for grape jelly, it’s a notable upgrade of a lunchbox fixture. 

Dolce Italian: Another creative spin on the PB&J-for-adults idea can be found at Dolce Italian. There must be something about chic Italian restaurants and PB&J novelties that just plays well together. Here, the PB&J Time cocktail contains whiskey, rye, peanut butter syrup and a beautiful blueberry ice cube. 

CH Distillery: The name says it all. The aptly dubbed Happy Ending at CH Distillery is a surefire way to cap off a night of dining and drinking in style. The booze-packed cocktail features both condensed and evaporated milk for sweetness and silky texture, along with vanilla beans, shaved chocolate and a trifecta of house-distilled spirits: CH Rum, CH Amaro and CH/Dark Matter coffee liqueur. 

Rockit Bar & Grill: Borrowing a page from one of the most beloved after-school snacks of all time, Rockit Bar & Grill has given milk and cookies an intoxicating makeover. Not only does the presentation of this cocktail look adorable, but it tastes just as precious, thanks to a medley of Aylesbury Duck vodka, almond milk, white chocolate, lemon, vanilla syrup and egg white. It’s served with a little cookie on the side for dunking as you please. 

Cafe des Architectes: Cocktails served with cookies is a trend we can get on board with. At Cafe des Architectes, they take it up a notch by not only serving their Bellini Float with almond cookies, but with a spoonful of Pop Rocks as well. The drink itself is pretty sweet too, made with Champagne, peach sorbet and raspberry pearls. 



Presidio: Fernet is king at this Bucktown cocktail bar. Not only does the bar serve its own custom Fernet, made at local CH Distillery, but the menu boasts an entire array of Fernets across a wide spectrum of flavors. Presidio even offers a dessert-y interpretation in the form of a Fernet milkshake, outfitted with rum, mint and chocolate chip ice cream. The whole thing makes for a refreshing, herbaceous finale. 

The Signature Room: Oatmeal cookies are a lot more intriguing when they’re not tricking you into thinking they’re actually chocolate chip cookies. And when they’re actually a cocktail infused with whiskey. The Signature Room features a fun riff on this cookie classic in martini form. At once sweet and spicy, it’s made with Fireball whiskey, Buttershots and Bailey’s Irish cream. 

Community Tavern: Coffee and rum come together in perfect harmony at Community Tavern, where Jose Cordon works wonders with after-dinner drinks. The Direct Trade cocktail eschews overt sweetness for something in between bitter espresso and mildly saccharine coffee. The house coffee liqueur for the drink is a blend of espresso, sugar, chocolate bitters and angostura, which gets stirred with rum, Ancho Reyes chile liqueur and coffee beans. 

Cafe Spiaggia: Courtesy of bartender Lov Carpenter, Cafe Spiaggia proves its mettle as a worthy cocktail contender in addition to its venerable wine program. This particular dessert drink is a smooth mix of Maker’s Mark, ruby port, Amaro Nonino, Grand Marnier, chocolate bitters and one egg. It’s all garnished with coffee beans and served up. 

GreenRiver: Mascarpone cheese isn’t typically something you’d expect to find in a dessert cocktail, but if anyone is going to debunk pre-conceived notions, it’s Julia Momose at GreenRiver. The crafty mix-master is behind the MacSwiney, a unique blend of Pierre Ferrand 1840 Cognac, creme de noyaux, kirsch, vanilla, lemon, mascarpone cheese and burlesque bitters. That cheese adds a welcome dessert-y richness and smoothness to the cocktail, with an added nutty component via the creme de noyaux. Altogether, the whole thing is almost like an after-dinner cheese plate. 

Carnivale: The quintessential carnival snack takes the cocktail stage at Carnivale, where the Cotton Candy Martini is equally fun and luscious. The playful cocktail features a base of Purity vodka, lime and grapefruit, with a puff of cotton candy nestled on top. As it dissolves into the cocktail, it adds some additional fruity sweetness.

The Purple Pig: One particular dessert drink at The Purple Pig captures the essence of a creamsicle, and then elevates it. The Orange Sherry Cream begins with a scoop of vanilla bean gelato, a couple shakes of orange flower and some orange zest. This is all poured with Nardini Bassano Amaro and some Pedro Ximenez sherry. 


The Windsor
The Windsor, photo by Monica Kass Rogers

The Windsor: At The Windsor, they keep it simple and indulgent with their adult milkshake. Because when you’re combining caramel, vanilla and Maker’s Mark, there’s no need to over-complicate something so simply satisfying. 

Allium: In regards to boozy milkshakes, Allium is one place that helped pave the way for the trend. The restaurant inside the Four Seasons Hotel Chicago has amassed a veritable fanbase for its miso butterscotch milkshake, which is all well and good on its own, but especially splendid when splashed with Fantasia Liqueur

Sink|Swim: The Italian affogato is sort of like the progenitor to American ice cream floats, and Sink|Swim serves a mean one for brunch or dessert. It’s cold-brew coffee with a dollop of maple ice cream and a dash of Fernet for some welcome herbaceous notes.  

Bernard’s Bar: When a cocktail bar borrows inspiration from Nutella, you know the results are going to be good. The Noce Dolce at Bernard’s Bar does just that, designed to emulate the habit-forming flavors of the chocolate-hazelnut spread. The drink is made with bourbon, Cocchi Americano, Frangelico, demerara syrup and chocolate bitters. 

- Matt Kirouac