Whether it's ice cream, gelato or frozen yogurt that strikes your fancy, Chicago has great ice cream shops serving up a perfect version of the icy dessert. We're crazy about the custard from Scooter's, the towering, colorful cone from Original Rainbow Cone and the inventive flavors served up at Jeni's. And that doesn't even count the best ice cream sandwiches, including versions made from doughnuts.
Chicago's best ice cream shops
Walk into Scooter’s and disregard the hot dogs, Italian ice and anything else that doesn’t contain the words frozen and custard. Order a Boston shake, and quiver in awe as the towering milkshake topped with hot fudge and whipped cream is handed over. As you taste how dense, thick, buttery and rich the custard is, you’ll soon be on your way to a full stomach and an ice-cream headache. And it’ll be worth it.
For more than 80 years, the awning-covered picnic tables of this Far South Side ice-cream shop have been packed with locals indulging their sweet tooth. The signature five-flavor Rainbow Cone features scoops of chocolate, strawberry, Palmer House (vanilla with cherries and walnuts), pistachio and orange sherbet stacked one on top of the other for an unbeatable classic.
When Ohio-based Jeni's moved into Southport Corridor it immediately upped Chicago's ice cream scene. Sweet corn ice cream with black raspberry swirls? It's got that. The richest, darkest chocolate ice cream you'll ever have? It's got that, too. When you factor in toppings like salted caramel sauce, the decision about what to order is that much harder. Luckily, Jeni's workers will provide you with as many samples as you want.
After peddling her gelato all over town to the city's best chefs and markets, Jessica Oloroso found a fitting home for her first storefront in Ukrainian Village. There, she lures folks with boundary-pushing scoops of gelato such as avocado-cinnamon and sesame-fig-chocolate chip. The mish-mash of tattooed bike-peddlers and stroller-pushing locals tends to sample plenty before settling, giving you more time to decide between a simple cup or a cone with a refreshing iced Turkish coffee on the side. Also check out Black Dog's Roscoe Village location.
What would a soda fountain be without an outdoor spot from which to watch the world go by? Late-night hours (till 11pm weekdays, midnight weekends) mean you can take in nocturnal antics while sipping a caffeinated “cream express” milkshake (vanilla and espresso). Or go earlier in the evening, grab a scoop of the Lakeview Barhopper (chocolate ice cream with Jack Daniel’s), and get a jump on the night’s festivities.
When you walk into SmallCakes, you're immediately surrounded by cupcakes, but ignore that (or maybe don't, they're quite delicious too). To the left, there's a small ice cream freezer that you'll want to focus on. All the ice creams are delicious, but keep an eye out for the ones they make with their house-made cakes, like red velvet and white cake, served in a waffle cone.
Sweet Occasions fans can stop their mourning: The ice-cream slinger that took over this space is practically identical to the previous tenant—only upgraded. The walls are decked out in grays and dark blues, and the food menu now includes hot panini, crêpes and waffles. Most important, the ice cream is the same (Chocolate Shoppe from Madison, Wisconsin). The scoops are now offered in over-the-top sundaes, but save the cash and the sugar overload—this ice cream holds up well enough on its own.
This West Loop ice cream parlor dishes out a crazy long list of scoops, but we'll make this simple for you. Pick the soft serve, whatever flavors are on. We're a big fan of the vanilla and red velvet swirl. There's milkshakes and malts, and you can get just about any ice cream topped with Lucky Charms (this place does have an Irish theme, after all).
This tiny Lakeview shop shares a space with Ms. T's Southern Fried Chicken, specializing in a la mode pies. You can also get regular scoops with funky flavors like honey graham cracker and whiskey chocolate. Seats are limited, but that's alright—we're perfectly okay with grabbing a cup to go.
This darling little ice cream shop is the perfect stop on your way to all of those great shops along California Avenue. Stop in and grab a cone of your favorite—we're fans of the peanut butter chocolate chip and the blood orange raspberry—and take a pint home too, while you're at it.