The best ice cream shops in Chicago

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 for 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. 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.

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? It's got that. 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.

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 three other locations. 

It’s nostalgia that draws people in droves to this kitschy diner/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.

What would a soda fountain be without an outdoor spot from which to watch the world go by? Late-night hours (till 10pm weekdays, 11pm 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.

This family-owned walk-up window is the stuff 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.

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.

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 craft using their house-made cakes—like red velvet and white cake—served in a waffle cone.

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.