This custard shop made local waves when pastry chef Jordan Rappaport told Chicago magazine he makes “the best cheesecake in the world.” Baker Boys creates nine custards and sorbets daily (flavors have included red velvet and malted milk balls), which Rappaport taste-tests before approving a full batch.
As a child, Joseph Sapp used his hard-earned pennies to buy ice cream. But the local parlor had only vanilla or chocolate, and he dreamed of more. Now 86 years after Joseph opened the Original Rainbow Cone, guests still line up for cones stacked with its signature 5-layer scoop of chocolate, strawberry, Palmer House, pistachio, and orange sherbet.
Belly Shack serves only four soft-serve dishes, but each one is quite distinct. Custom toppings from Hot Chocolate’s James Beard award-winning chef Mindy Segal transform sundaes with bacon chocolate chip, huckleberry lime, mint brownie, or Vietnamese cinnamon caramel.
Once a pastry chef under Stephanie Izard, Jessica Oloroso has since created Black Dog Gelato, where guests can try flavors crafted from Midwestern fruits. Taste quirky creations such as goat cheese cashew caramel and Mexican hot chocolate. For a boozy yet creamy treat, diner can try the whiskey gelato bar, which comes dipped in chocolate and sprinkled with bacon crumbles.
For many Chicagoans, unpacking winter coats and gloves coincides with the shelving of ice-cream cravings. That’s not the case for Bobtail and its Steamer, ice cream steamed with milk until it’s toasty enough for a blistery January day. Bobtail also brews ice-cream lattes, which layers the milk-steamed ice cream over espresso.
Native Italian Cristiana Ginatta ate her grandfather’s gelato as a child, and eventually studied the art herself at a renowned gelateria in Turin. When she and her family moved to the states, Cristiana founded Paciugo, a Dallas-based gelato chain where patrons choose from an encyclopedic list of unique flavors, ranging from orange saffron to violet chocolate chip.
Though Portillo’s nearly 50-year history has been built mainly on hot dogs and burgers, a meal inside the popular local chain isn’t complete without a milkshake. The flavors are mostly simple—shakes and malts in chocolate, vanilla, or strawberry). But try the extra-decadent chocolate cake shake, which clogs straws with chocolaty ice cream and chewy chunks of cake.
The futuristic iCream cream offers 256,000 flavor combinations of ice cream, sorbet, and frozen yogurt. Here, ice cream is created instantaneously, as every cup is made by flash-freezing fresh ingredients in a mixer infused with liquid nitrogen that’s 320 degrees below zero.
The Beatles and the Rolling Stones have one surprising thing in common: their taste in ice cream. Both bands ate at Margie’s, an ice-cream parlor that’s been open nearly 100 years. Over time, Margie’s has produced many specialties: extra-thick shakes, massive all-natural sundaes in clamshell dishes, and hot-fudge sauce so popular you can get it to-go.
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At Lickity Split, you can taste the baked goodies of several other Chicago bakeries. Delve into red-velvet cake bowls from Phoebe’s Cupcakes combined with vanilla custard, marshmallow crème sauce, and red raspberries, while Celestial Kitchens’ peanut-butter fudge compliment Lickity Split’s chocolate custard.
Grange Hall boasts its own in-house ice creamery, using seasonal ingredients harvested from local farmers to create the freshest flavors possible. The rotating menu has included everything from peanut butter and jelly to sweet corn (which can all be purchased to-go); more traditional diners can also get scoops of Homer’s ice cream in chocolate or vanilla.
Scoops is the type of place where anything is possible—ice-cream cake is portable, whole slices of pie fit into a Blizzard, and people put toppings not just on their ice cream, but also their cones. Scoops serves more traditional classics as well, including banana splits and root-beer floats.
Winner of James Beard Foundation’s award for Outstanding Pastry Chef in 2012, Mindy Segal of Mindy’s Hot Chocolate regularly creates new and exciting desserts. Here you’ll find stout-and-caramel milkshakes, apple-cider sorbet, and chocolate souffled tarts with burnt-honey ice cream.
Pastry chef Craig Harzewski incorporates NAHA’s Mediterranean influences when crafting the restaurant’s desserts, pairing strawberry-mint sorbet with goat cheese, olive-oil ice cream with custard cake, and pistachio ice cream with sweet cherries. Feel free to ask for solo scoops from the rotating selection of ice creams and sorbets made in-house.
In Nightwood’s kitchen, it takes more than a scoop of vanilla to make something à la mode. Blueberry-pancake ice cream tops the blueberry crisp, and lemongrass ice cream enhances the flavors of the blackberry yellow cake. Grab a scoop of the ice cream du jour in a vanilla cone—flavors have included honey-lavender and milk chocolate.
NoMI pastry chef Meg Galus Is serious about dessert, even saying that “pastry sustains the soul” in her bio. When it comes to ice cream, NoMI makes port-dark-chocolate and peanut-butter malt ice cream in house, as well as blueberry violet sorbet.
Scooter’s frozen custard is called “Concrete” because it’s so thick that you can actually turn it upside down, even when cookies or candy are mixed in. And though it’s thick, it’s not heavy. Scooter’s custard boasts about 40% less butterfat than some ice creams. Aside from Concretes, the menu rotates flavors of the day, which have included cinnamon and black-raspberry truffle.
After sashimi or Japanese-inspired tapas, patrons can dig into the an mitsu: green-tea ice cream layered with chilled red beans, lemongrass, ginger, and chewy cubes of agar agar. The chefs also serve sea-salt or black-sesame ice cream.
Even if you haven’t been to Snookelfritz, you may have tasted chef Nancy Silver’s desserts before—she makes the avocado ice cream for Big Star’s milkshakes and the ice-cream sandwiches for Violet Hour. A regular at the Green City Market, Nancy uses ingredients from fellow vendors to make seasonal ice-cream flavors, such as pear and brown butter.
Chi Scream’s recipe for success is simple: take delicious cookies and ice cream and put them together. If you’re lucky enough to come across one of Chi Scream’s bicycle carts, try one of its inventive sandwiches, such as peanut-butter-banana ice cream between triple chocolate cookies, or apple-pie-filling ice cream between oatmeal cookies.
Heavenly Cafe offers the trifecta of frozen desserts: ice cream, gelato, and sorbet. The café’s vegan, soy-based ice cream come in flavors such as black walnut, while the gelato selections explore quirky but popular blends, like Mexican chocolate chipotle.
At Sugar Shack, guests don’t just get to build their own custom sundae, they get to build it on top a funnel cake. Vanilla soft serve covers the carnival classic, which can then be topped with one sauce (yes, peanut butter counts as a sauce) and one topping, with choices including brownie pieces and cookie dough.
Considering they’ve been serving ice cream since 1901, it’s no wonder Gertie’s menu leans toward the nostalgic. An old-fashioned banana split comes beneath familiar layers of strawberry, pineapple, and chopped nuts. Two scoops of ice cream thicken chocolate or cherry sodas in Gertie’s floats, while whipped cream top triple-rich butterscotch or peanut-butter malts.
Deal or no deal, our editors strongly recommend these businesses based on their reputation, popularity, and quality of service.