Desserts to Die For

Having a sweet tooth is so underrated. Pizza–delicious. Cheeseburgers and fries–yes, please. But if you really want to indulge, nothing beats a flourless chocolate cake, bread pudding with extra caramel sauce or a slice of pecan pie with vanilla ice cream. Why not do as writer Ernestine Ulmer once said, “Life is uncertain. Eat dessert first”? After all, ’tis the season for keeping warm via comfort food. There are many hidden treasures, along with restaurants already known for their sweets, and they are all right in your backyard. Here are some great desserts to live, or perhaps die, for.

Hot Chocolate

1747 N. Damen, 773-489-1747

Although the name suggests otherwise, there’s something for chocolate and non-chocolate lovers alike at this sleek and hip, Bucktown hotspot. Mindy Segal, MK alumna and acclaimed pastry chef, centers the menu around fabulous desserts, but there are also solid brunch and dinner options, such as a hamburger made with farm-raised beef and aged cheddar, a tuna melt and entrees including free-range chicken and fresh fish. Chocolate lovers won’t have a hard time ordering dessert here, as there are several cocoa-heavy treats like the “percentages.” The Chocolate 72% is a chocolate fudge mint cake that tastes like a rich brownie made of Girl Scout Thin Mints, accompanied by more fudge mint in the form of a small, shooter-sized shake. Another winner is the Chocolate 35%, a rich, Valrhona milk chocolate and peanut mousse terrine that has a caramel center and sides of peanut brittle and malted milk foam. Too much? How about just a cup of the famous house hot chocolate made with real cocoa and marshmallows. Or opt for one of the fruity desserts, such as the Black and Blue, a sandwich made with citrus shortbread and lemon curd, served with sour cream sorbet and poached, organic blueberries and blackberries.

Osteria di Tramonto

601 N. Milwaukee, Wheeling, 847-777-6570

There comes a time in everyone’s life when they must try something sweet made by Gale Gand, pastry queen of Chicago–and the country, for that matter. Gand’s stellar reputation and award-winning prowess comes from her success as executive pastry chef at Tru, the legendary, four-star downtown restaurant she runs with longtime culinary partner and acclaimed chef Rick Tramonto. Gand also hosts “Sweet Dreams” on the Food Network. Now, she and Tramonto have teamed up to open this lively Italian restaurant tucked in the Westin Chicago North Shore hotel. Ordering at least two of Gand’s ethereal desserts here are a must. If in a bind over which to pick, try this: close your eyes and point to anything on the menu–you’re guaranteed to wind up with something extraordinary. The profiteroles, four pastry shells filled with unique flavors of gelato, such as caramel, hazelnut or espresso, are all doused in a rich, warm chocolate sauce. Or try the orange ricotta cannoli–deep-fried wonton shells filled with citrusy ricotta, atop a dusting of pistachios and white and dark chocolate shavings for dipping. With a buttery crust, seasonal apples, a silky-rich caramel sauce and vanilla gelato, the apple crostata is another crowd favorite.

Sweets and Savories

1534 W. Fullerton, 773-281-6778

At this cozy, intimate spot in Lincoln Park, the menu lives up to the restaurant’s name. Sweet chocolate finds its way into a savory beef tenderloin dish, mashed potatoes mix with mascarpone and a fig “ketchup” accompanies duck fat fries. And the sweet stuff doesn’t stop there–David Richards, executive chef, is also known for his scrumptious desserts. A bestseller is the chocolate fondant cake–a warm, molten chocolate cake baked to order and accompanied by a scoop of chocolate sorbet and generous drizzling of rich chocolate ganache sauce. Another favorite is the milk chocolate, warm pecan pie with a burnt caramel- and brandy-accented soft center, marbled with melted chocolate and large pecan chunks and enveloped by a flaky butter crust. That alone would be superb, but the pie is then topped with a scoop of cocoa-dusted, Tahitian vanilla bean ice cream, which balances the sweetness of the caramel sauce on the plate.

Angelina Restaurante

3561 N. Broadway, 773-935-5933

You truly have not lived or you haven’t lived well until you’ve had the bread pudding at this romantic, hidden gem in East Lakeview, which serves homemade and authentic Italian fare. Their traditional Italian bread pudding has a milk chocolate twist. Many bread puddings can be soggy and too wet, but this pudding stays semi-firm, yet moist and rich, studded with the chocolate chunks, which, having only slightly melted, maintain their shape and add a surprise factor to every bite.


18 E. Bellevue, 312-642-3400

If you’re going to order dessert, you might as well go all out. The Snickers pie at this Gibsons-owned hotspot in the heart of the Gold Coast will knock your socks off–in terms of both its size and taste. The massive heap of ice cream embedded with layers of Snickers bits, chocolate, caramel and peanuts, serves at least eight people. Although the pie sounds like it would be too sweet, lovers of the treat swear by the stuff because of the good balance of ice cream to candy bits.

Dunlay’s on the Square

3137 W. Logan, 773-227-2400

Remember those chocolate chip cookies your mom or perhaps grandma used to bake that you’d eat right out of the oven with a glass of milk? The giant cookie at this Lincoln Square, friendly neighborhood restaurant is the same idea, except the milk is replaced with a generous scoop of rich vanilla ice cream. Crispy on the bottom and warm and oozing velvety chocolate on the inside, this giant cookie bakes in a cast-iron skillet, gets a drizzling of caramel sauce and then goes directly to your table. You will think you have died and gone to heaven. custom dress socks

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