Start off with an obvious one and head to Mindy’s HotChocolate in Wicker Park. They’re open year-round but are clearly most popular when the temperature drops. Try out their namesake hot chocolate that comes in a seemingly endless amount of combinations. You can even buy giant bags to bring home and enjoy all the time. Don’t forget about their extensive food menu that changes with the seasons – enjoy it for brunch or dinner.
Mindy’s HotChocolate, 1747 N Damen Ave, Chicago, IL, USA, +1 773 489 1747
Xoco, 449 N Clark St, Chicago, IL, USA, +1 312 661 1434
Meal service:All Day
This well-known upscale coffee chain may not be the cozy local neighborhood cafe, but it makes a quality cup of cocoa. Intelligentsia started on Chicago’s North Side in 1995, and it has since expanded to New York and LA. As long as you can handle the strong scent of coffee beans and the slight air of pretension, it’s one of the best places to grab a mocha in the Loop. It has several locations dotted around the city, which means you never have to walk far for your sweet fix.
Hershey’s Chocolate World
The Hershey’s Store in any city is bound to be a tourist trap, but it’s also an unforgettable experience. Try to visit at an off-peak time to avoid the crowds, but be sure to stop in with the little ones. They can be a ‘factory worker’ who helps fill their buckets with candy before picking out their favorite sweet merchandise. Don’t leave before visiting the sweet shop in the back where you can try everything from hot chocolate to fudge brownies.
Hershey’s Chocolate, 822 N Michigan Ave, Chicago, IL, USA, +1 312 337 7711
If you’re a University of Chicago alum, you’re probably already well-acquainted with Medici. It’s an American restaurant, bakery, and delicatessen all rolled into one that serves up quality pizza, burgers, and sandwiches to students and locals alike. In the winter, they also offer hot cider, Mexican hot chocolate, and classic cocoa. Try the Medici Mocha and Mexicana shake for a twist on the sweet drinks.
Medici on 57th, 1327 E 57th St, Chicago, IL, USA, +1 773 667 7394
Katherine Anne Confections
The best hot beverage you can get in Logan Square comes from Katherine Anne Confections. The quaint shop is loaded with truffles, caramels, marshmallows, and candies of all kinds. They have 10 different flavors of hot chocolate alone, so it’s hard to run out of options here. You can even buy your own containers to enjoy at home on winter days so cold that you can’t bear to step outside.
Katherine Anne Confections, 2745 W Armitage Ave, Chicago, IL, USA, +1 773 245 1630
Millennium Park is always an extraordinary place to celebrate the winter season as it’s typically packed full of activities. You can ice skate at the seasonal rink or down the Maggie Daley ice ribbon, take pictures with a snow-capped Bean, or listen to holiday carolers in the park. You can also enjoy a tasty meal at the Park Grill and warm up after a day of fun with their rich hot chocolate.
Park Grill, 11 N Michigan Ave, Chicago, IL, USA, +1 312 521 7275
George’s Ice Cream and Sweets
George’s has been a neighborhood favorite on the main drag of cutesy Andersonville since opening in 2009. You’re bound to find this parlor full of families on the weekends, with others walking their dogs past the window. The menu is huge and typical of a sweet shop, but they offer six different specialty hot chocolates year-round. Try the pumpkin cocoa for now and work your way up to Nutella and mint.
George’s Ice Cream and Sweets, 5306 N Clark St, Chicago, IL, USA, +1 773 271 7600
After a long day of holiday shopping on Michigan Avenue, turn off on Pearson Street for a sweet treat at Ghirardelli. An employee almost always hands you a free piece of chocolate when you walk through the door that you can snack on while browsing the assortments and selection of candy they have on display. But it’s also a sit-down dessert shop where you can order specialty hot chocolates, sundaes, shakes, cakes, and more – pure decadence.
Ghirardelli, 830 N Michigan Ave, Chicago, IL, USA, +1 312 337 9330
Julius Meinl has been a Vienna-based coffee roaster since 1862 and is a well-established name in central Europe when it comes to coffee beans. Expect a long list of Austrian pastries, a warm atmosphere, and plenty of cushy chairs to sink into while you enjoy your hot drink. From hot chocolates to teas and the best coffee in Austria, there’s plenty of hot beverages from which to choose. Visit one of their three North Side locations.