Peanut Butter Shake at DMK Burger Bar: DMK is better known for its delectable burgers and fries; a shame, given that the peanut butter shake is sinfully good. Easily a dessert for two people, the shake is blended with peanut butter and layered with caramel and fudge—you will swear that you stuck a straw into the tastiest, creamiest jar of peanut butter in the world.
DMK Burger Bar
2954 North Sheffield, Chicago, IL 60657 (map) 777-360-8686; DMKburgerbar.com
Boston Shake at Scooter's Frozen Custard : Fans of Scooter's know that they have the creamiest dessert product in the entire city; in fact, some of those fans objected to my suggestion that it be blended into a shake. Enter: The Boston Shake—a full size shake (we got cookies and cream) with an entire scoop of frozen custard on top, drizzled with hot fudge. You say best of both worlds, we say tasty.
Scooter's Frozen Custard
1658 W. Belmont Avenue, Chicago, IL 60657 (map)773-244-6415; scootersfrozencustard.com
Chai Shake at Charmers Cafe: While they occasionally have some astounding specials (basil milkshake? yes please!) their chai milkshake, available every day, is enough to keep me satisfied. Its spicy flavor, combined with vanilla ice cream, tastes like the best ginger snap you've ever had.
1500 W. Jarvis Avenue, Chicago, IL 60626 (map) 773-743-2233; www.charmerscafe.com
Peanut Butter Cookie Dough Vegan Milkshake at Chicago Diner: Some carnivores will mock me for this, but possibly the best shake on this list came from a vegan restaurant. That's right, folks, no dairy at all—but I dare you to not slurp the whole thing down. With chunks of vegan cookie dough, Temptation frozen Dessert (by Chicago SoyDairy) and beet sugar, you can almost feel good about devouring the whole thing in 45 seconds.
The Chicago Diner
3411 N. Halsted, Chicago, IL 60657 (map) 773-935-6696; veggiediner.com
Strawberry Banana Milkshake at Medici on 57th: This Hyde Park classic is a great spot for a casual lunch, and its milkshakes and malts have one really distinctive factor—the huge dollop of handmade whipped cream on top. It's like a huge pat of butter on top of the milkshake. Combined with a strawberry banana milkshake, it'll satisfy your RDA for fat for a month, and it's worth every gram.
The Medici on 57th
1327 E. 57th Street, Chicago, IL 60637 (map) 773-667-7394; www.medici57.com