The best ice cream in Chicago
Inspired by the memory of standing at the end of her driveway with change in her pocket, waiting on the ice cream truck, Dana Salls Cree opened Pretty Cool Ice Cream in Logan Square. The cute-as-a-button shop slings beautiful popsicles in fascinating flavors. Lick a peanut butter-potato chip custard bar, a plant-based blue moon pop or a strawberry buttermilk bar. If you close your eyes, you can almost hear that classic ice cream truck jingle from your childhood.
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 layers of chocolate, strawberry, Palmer House (vanilla with cherries and walnuts), pistachio and orange sherbet stacked one on top of the other to form an unbeatable classic.
Walk into Scooter’s and disregard the hot dogs, Italian ice and anything else that doesn’t contain the words frozen and custard. Purists should order a cone of vanilla or chocolate and savor every last lick of the cream-laden treat. If you're hankering for something a bit more involved, opt for the banana splice: vanilla custard, banana, chocolate, strawberries, pineapple and nuts. It's big enough to split, but we won't judge if you're selfish.
It’s nostalgia that draws people in droves to this kitschy diner and ice-cream parlor. Fancy silver trays, paper doilies and saucers filled with chocolate and caramel sauces bring back fond memories for many who’ve made this place a tradition since it opened in 1921. Equally reminiscent of the good old days are the display shelves, which are crowded with memorabilia from the Beatles, who just had to have some Margie’s ice cream after they played Comiskey.
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. If you're downtown, check out her stall inside Revival Food Hall for a quick fix over the lunch hour.
When Ohio-based Jeni's moved to Chicago, it immediately upped the city's ice cream scene. Sweet corn ice cream with black raspberry swirls? Check. The richest, darkest chocolate ice cream you'll ever taste? 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.
The Freeze is a vintage time warp, and while there aren’t nearly as many locations of the fast food restaurant (formerly known as Tastee Freez) as once dotted Chicago (there were dozens), you can still find one in Logan Square. Waffle and sugar cones are filled with a high peak of soft serve and dipped in throwback flavors like butterscotch, cotton candy and peanut butter. If you're looking for cheap, no-frills thrills, the Freeze has you covered till 10pm Tuesday through Sunday.
The Edgewater shop turns out rich and creamy custard, which you can get whipped into sundaes and concretes like the aptly named OMG—chocolate or vanilla custard dotted with peanut-butter fudge brownie pieces and a shot of hot fudge. As if that weren't enough, you'll also find cookies, cupcakes and beautiful chocolates behind the counter.
This family-owned walk-up window is the stuff that dreams are made of. From funnel cake sundaes and ice cream tacos to Italian ice and banana splits, you might just experience a sugar rush while browsing the menu. Order whatever makes your heart happy and take a seat at one of the umbrella-covered tables—you're in for a treat at this Bridgeport shop.
The vibrant paleteria only opened its Pilsen location in mid-2015, but with several other area locations under its belt, it's already polished. The dozens of paletas available are among the city's best, with rich cream flavors like blackberry or fruity kiwi frozen with fresh strawberries. Or go for something more traditional with a scoop of ice cream, with flavors like bubblegum, coconut and Nutella.
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.
The list of Italian ice at this Armitage Avenue walk-up shop is ridiculously long, but so is the ice cream inventory. The patio seats are perfect for sitting out with a cake cone and a scoop of your favorite flavor (we like the raspberry with chocolate ripples and raspberry cordials).
This darling ice cream shop is the perfect stop on your way to all of those great shops along California Avenue. Hop in and grab a cone of your favorite—we're fans of the peanut butter chocolate chip and blood orange-raspberry—and take a pint home too, while you're at it.
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 of the flavors are delicious, but keep an eye out for the ones they craft using their house-made cakes—like red velvet and white cake—served in a waffle cone.
This West Loop parlor dishes out a crazy long list of scoops, but we'll make this easy for you. Pick the soft serve, whatever flavors are on (we're all about the vanilla and red velvet swirl). There's milkshakes and malts, and you can get just about any ice cream topped with Lucky Charms.
You’ll feel as though you stepped into a Sicilian gelato bar at this little spot, where everything (from the chocolate and nuts to the furniture and gelato machines) is imported from Italy. All flavors are made in fresh batches daily, including rich, creamy hazelnut, Stracciatella, peanut butter with brownie, pistachio and Bacio (a chocolate and hazelnut blend named for Baci candies). Seasonal fruit gelati and sorbets also fill the menu, as do a couple of panini and expertly made Illy coffee drinks.
The aroma of fresh waffles pervades the air of this Bridgeport parlor, evidence of the signature house-made waffle cones. Dipped in chocolate and adorned with brightly colored candies, these deep cones are indulgent carriers for both types of chocolate ice cream on offer (though our preference is for the darker variety). Should the ice cream be too rich, you’re in luck: Like all good Italians, these guys focus on espresso, the perfect antidote to your forthcoming sugar crash.