The Merriest Dishes and Drinks in Chicago

Remember: if you don't consume peppermint, eggnog, and gingerbread by the metric ton this holiday season, you will be added to the naughty list. Fortunately, meeting that merry quota is easy in Chicago, where restaurants, bars, and bakeries are chock full of jolly Christmas-y dishes and drinks. Consider this your edible bucket list for holiday dining in Chicago: 

Chop Shop
(Chop Shop)

Summer House Santa Monica: The motif may scream "California beach body!" but the food is as enriching and merry as you'll find in Chicago at Summer House Santa Monica. Try the house eggnog made with grated cinnamon and brandy, or for something to snack on, the bakery has peppermint cookies and gingersnaps in their arsenal. 

Chop Shop: From peppermint-infused cocktails to creamy-rich Tom and Jerrys, Chop Shop has your bases covered for cozy imbibing this season. Try the Saulte Nonno! made with Fernet Vittone Menta, housemade spearmint-peppermint syrup, Heering Coffee, Cardamaro Vino Amaro, Fee Bros. Aztec Chocolate Bitters, and mint; or go full-force with the house Tom and Jerry, a boozy dessert-in-a-cup of rum, Cognac, SomruS liqueur, housemade Tom and Jerry batter, winter spice syrup, cream, and nutmeg.

Trenchermen: Right next door from Chop Shop is another apt peppermint potable. Trenchermen wins the award for most adorable cocktail name this season with their St. Nick-Groni, featuring candy cane steeped in Bombay Sapphire East Gin, Campari, sweet vermouth, and a candy cane garnish. Ho ho ho! 

BOKA: Here's how it's going to go down at BOKA in your near future. You're going to gingerly sip the 90° Latitude Cocktail made with Bombay Dry, peppermint, Campari, egg white, and pink peppercorn, and you're going to chase it with the spice-tasting chocolate cake bedecked with huckleberries, gingerbread, and cardamom ice cream. 

Kama Indian Bistro: Gingerbread takes an eclectic turn at Kama Indian Bistro, not the first place you'd expect to snack on gingerbread, let alone sip it in a cocktail. Here, the bar impresses with a creamy Indian-spiced tipple outfitted with Frangelico, Laphroaig Single Malt Scotch, Domaine de Canton ginger liqueur, and Kama spiced syrup. 


Francesca's: Celebrate holiday dining the Italian way at the Francesca’s pantheon of restaurants with their Christmas-flavored Vasi Al Formaggio di Menta dessert. This thing is Santa's dream come true, containing dual flavors of gingerbread and peppermint. Presented in a cute jar, it contains layers of peppermint cheesecake, gingerbread crumble, crushed peppermint candy, whipped cream, and berries. 

Revolution Brewery: One of the best holiday traditions, even more vital than caroling and ice skating, is the release of Revolution's Fistmas Ale, a veritable can full of Christmas. The best part about this bracing quaff is the boatload of ginger in it, which snuggles up quite nicely in the brewing process with orange peel. Altogether, it makes for a nice alternative to capture those holiday flavors minus any of the treacly excess.

M Burger: People who say milkshakes and ice cream are mere warm-weather desserts not worthy of holiday cravings alongside pie and hot chocolate can go to hell. Consider this: M Burger's milkshakes of the month are currently eggnog and peppermint, two luscious desserts sure to disprove any preconceived notions that it's too cold for milkshakes. Just don't consume them in shorts while standing outside and you'll be fine. 

Siena Tavern: And while we're on the topic of shaming ice cream naysayers, let's head on over to Siena Tavern and sink our faces into a mound of peppermint bark gelato. It's the flavor of the month for December, courtesy of corporate pastry chef Amy Arnold, and it's a doozy of a dessert, made with a peppermint base, candy canes, and white chocolate pieces strewn throughout. 

Chicago q: Wouldn't you know it, there's even more milkshake goodness to be found this season, thoroughly debunking the taboo notion that the holidays are exclusively pie season. Chicago q is offering their milkshake and cookies combo dessert with an eggnog bourbon milkshake, accompanied by oatmeal-bacon cookies, chocolate chunk cookies, and white chocolate cranberry cookies. 

Siena Tavern
(Siena Tavern)

Magnolia Bakery: One of the absolute best desserts of the holidays can be found at Magnolia Bakery. A merry riff on their staple icebox layer cake, the cutesy cake shop has brought back their peppermint rendition, featuring handmade chocolate wafer cookies striated with peppermint-scented whipped cream, stacked up to the heavens.

River Roast: There's a new contender for most whimsical cocktail name this season, and it's happening at River Roast: The "Magical Elves Made This" cocktail features gingerbread cookie stock (!), El Dorado 12, Old Weller Antique, Batavia Arrak, and fresh nutmeg. 

Floriole Cafe & Bakery: If eggnog creme brûlée doesn't sound like perfection to you, check your pulse right now. It's back on the menu at Floriole Cafe & Bakery, along with housemade eggnog served virgin or spiked. Gingerbread-wise, the cafe is also baking up dark gingerbread cakes glazed with brandy caramel. 

Rustic House: When one creme brûlée just isn't enough, there's a whole trio being served together at Rustic House, one of which is peppermint-flavored. The others are nothing to scoff at themselves, made with chocolate and Bailey's. 

- Matt Kirouac