A's List: These local sweet retreats bring on cheer, atmosphere

By Audarshia Townsend

When it comes to indulging in great desserts, there’s certainly no shortage in Chicago. We’ve got award-winning pastry chefs crafting their art at some of the city’s hottest restaurants. Of course, there are the old-school neighborhood favorites, ranging from vintage bakeries and ice-cream parlors to classic doughnut shops.

And then there are the specialty dessert cafés and lounges. Cool, trendy and catering to families as well as to late-night crowds, these decadent destinations push the boundaries with unique offerings. Our favorites include over-the-top milkshakes at various venues to bubble waffle sundaes in Chinatown.

BomboBar (1529 N. Wells St., Old Town)

If you’ve ever rolled through the West Loop, surely you’ve seen the line over at Bar Siena. Well, technically that line is adjacent to the restaurant, and it’s leading toward BomboBar, which consists of a walk-up window and patio seating. Through the window, customers may order chocolate milkshakes heaving with toppings like Oreo cookie crumbles, blue stardust glitter and whipped cream; hole-less Italian doughnuts called Bomboloni—injected with Nutella or vanilla bean custard; and gelato sandwiches decorated with chocolate pretzels, gummy bears or caramel drizzle. There is always a line, whether it’s during the day or later at night, which is why the owners decided to open this larger BomboBar in Old Town. Here, you’ll find the same sweets, plus booze on tap, a signature burger and pizza by the square. At this location, there are also sugary snacks for pups, including dairy-free gelato, doggie doughnuts and woof cream.

JoJo’s Milk Bar (23 W. Hubbard St., River North)

Inspired by Momofuku restaurant group's Milk Bar concept, a dessert-focused cocktail lounge in Manhattan, JoJo's features offbeat pastries, ice-cream treats and more. The atmosphere is colorful and playful, with over-sized illustrations of Bill Murray, Queen Elizabeth and Notorious B.I.G. sporting milk mustaches. During the day, JoJo's is family friendly, and at night (guests must be at least 21 after 9pm), they're cranking hardcore hip-hop music in a clubby setting. The menu offers savory dishes as well with classics like baked macaroni and cheese, a honey fried chicken sandwich and signature burger. But let's be real. Customers come for the desserts, which are Executive Chef Christine McCabe's specialty. There are artisan frozen milk bars in fun flavors (cherry chocolate, blueberry lavender, Snickerdoodle, Chai-town), a milk-and-cookies flight with infused milks, hot chocolate, and boozy shakes topped with doughnuts, waffle cones and whipped cream.

Joy Yee Plus (2159 S. China Pl., Chinatown)

What sets Joy Yee Plus apart from other Pan Asian eateries in the city is that it's the only place serving Taiwanese-inspired bubble waffle sundaes. Theirs are made to order—with freshly made bubble waffles—as well as freshly cut fruit and other toppings to create outrageous, eye-catching delights. Favorites include Strawberry Paradise (strawberry ice cream, strawberry sauce, whipped cream, fresh strawberries and kiwi) and S'Mores (chocolate ice cream, chocolate sauce, miniature graham crackers, miniature Oreos, torched marshmallows, whipped cream). Those wanting something not as decadent should opt for bubble teas filled with fresh fruit as well as Joy Yee Plus’ take on shakes and smoothies.     

Pretty Cool Ice Cream (2353 N. California Ave., Logan Square)

Celebrated pastry chef Dana Cree—who was the former executive pastry chef for Blackbird and Publican—teams up with the proprietor of Bang Bang Pie Co. for this artisan frozen milk bar shop. It’s all they sell, so you just know they do it well. The original recipes, mostly based on her first book, "Hello, My Name Is Ice Cream: The Art and Science of the Scoop," are well represented behind Pretty Cool Ice Cream's counter. They range from chocolate peanut butter brownie crunch and Ricky's pretzel coffee toffee to strawberry sherbet and grasshopper. The venue is bright and cheery, family friendly and interactive. Guests may be seated on elevated blocks or hang out near the Instagrammable wall with magnetized letters.

Twisted Cookie (7401 Madison Street, Forest Park)

This charming little dessert café is situated in the heart of downtown Forest Park. Twisted Cookie's signature item is the cupcake cookie, which consists of two butter cookies topped with frosting and decorated like cupcakes. Favorites range from red velvet and triple chocolate to key lime and PB&J. There are also cheesecake cookies, cookie pies and cookie bark. Non-cookie items include dipped-and-stuffed fudge brownies (salted caramel, turtle and peanut butter are options), soft-serve ice cream and sundaes.

See previous A's List columns right here.