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8 great ice cream sandwiches in Chicago

Ice cream shops are taking the humble ice cream sandwich to new heights by using waffles, macarons, doughnuts and more

Photograph: Martha Williams
Bobtail serves one of the best ice cream sandwiches in Chicago.

Ice cream sandwiches have come a long way from the neatly folded rectangles of wax paper from your childhood. These days, anything goes—sandwiches are being made with everything from gigantic cookies to doughnuts, waffles and even macarons. All those options can be overwhelming, so we’ve compiled our favorite ice cream shops and other places to get these grab-and-go treats.

Black Dog Gelato

Glazed and Infused’s doughnuts and Black Dog’s gelato have become Chicago’s hottest power couple. This summer, their ice cream sandwiches are available on Mondays at both Black Dog Gelato locations until they sell out. Two doughnuts are available each week, and can be filled with your choice of gelato.

With doughnut options ranging from Blueberry Lemon and Maple Bacon Long-Johns, and gelato flavors like Goat Cheese Cashew Caramel, Mexican Hot Chocolate and Blueberry French Toast, the possible flavor combinations are endless. We opted for a simple vanilla bean gelato in the Red Velvet doughnut, but it was the giant apple fritter, split open and filled with three generous scoops of milk stout gelato that will haunt our summer daydreams.

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East Village

Bobtail Ice Cream Company

With its look of an old-fashioned soda fountain, it’s easy to see why Lakeview’s Bobtail Ice Cream is so popular. Here it features Chicago-inspired flavors like Cubby Crunch (vanilla ice cream with sprinkles, crushed cookies and toffee) and Daley Addiction (vanilla ice cream with a butter fudge swirl). While you can get a traditional sandwich, you can also get an open-faced ice cream sandwich. Served on a warm chocolate chip cookie, you can choose your flavor of ice cream (we recommend the classic vanilla) before your dish is drenched in hot fudge and whipped cream. We promise that you won’t mind having to eat it with a spoon.

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Lake View

Cookies & Carnitas


This cozy BYOB in Edgewater specializes in plate-sized cookies, which greet you in a glass case at the front of the restaurant. The cookies come in a variety of flavors, but standouts include the Peanut Butter, a chewy peanut butter cookie topped with a glob of jam, and the Kitchen Floor, filled with chocolate chips and flakes of sea salt, then rolled in espresso grounds. The already massive cookies are dwarfed by the ice cream sandwiched between them—there’s almost an entire pint of Häagen-Dazs vanilla—and rolled in your choice of chocolate chips or crushed peanuts. Unless you have the appetite to down an entire softball-sized ice cream sandwich, ask to have it cut in half (or in quarters) to share.

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Firecakes Donuts

It’s hard to imagine something as gluttonous as a doughnut stuffed with ice cream being delicate and light, but at Firecakes Doughnuts in River North, they’ve managed to pull off a little bit of pastry magic. While it’s easy to get caught up in the stunning array of creative doughnuts (Valrhona Chocolate & Espresso Cream doughnuts or a Rhubarb & Bourbon Glaze Fritter), don’t miss out on the simplicity of their doughnut ice cream sandwich. Each ice cream sandwich is made-to-order with either vanilla or pistachio ice cream (also made in house). It’s finished with a drizzle of chocolate sauce and placed into a split open, impossibly light yeast-raised doughnut with vanilla glaze. Be careful: Since they seem as light as cotton candy, you could easily eat two (or three).

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River North

Jeni's Splendid Ice Creams

Ohio-based Jeni’s Splendid Ice Cream opened their first Chicago location last summer on Southport, and the ice cream comes in a variety of creative flavors, like Bangkok Peanut and Brambleberry Crisp. They also offers four ice cream sandwiches that are available year-round, including three flavors that use large, chewy macarons as the cookie shells. Their classic Oatmeal Cream sandwich is crisp out of the freezer, with two cinnamon oatmeal cookies stacked around a generous scoop of Jeni’s Ndali Estate Vanilla Bean. Just for the summer, their Chocolate Truffle sandwich filled with Backyard Mint is a treat—two fudgy, sticky and bittersweet chocolate chocolate-chip cookies are paired with Jeni’s fresh and simple mint ice cream.

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Bridgeport ice cream shop Scoops serves up a full menu of treats, featuring everything from shakes and elaborate sundaes to ice cream cakes. You can pick up one of their ice cream sandwiches in their freezer case, which is filled with an assortment of mix-and-match choices. Chewy, buttery peanut butter and chocolate chip cookies are sandwiched with one of the 32 different varieties of ice cream offered, then rolled in one of a variety of toppings—sprinkles, crushed peanuts, chocolate sandwich cookies and peanut butter cups, among others.

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Scooter’s Frozen Custard

You can’t top the creamy texture of dense frozen custard. Scooter’s offers classic vanilla and chocolate flavors, made fresh from scratch every day, as well as a flavor of the day (which can be viewed on their website), ranging from Pistachio to Black Raspberry Truffle. The chocolate wafer cookies used in their custard sandwiches are the classic bittersweet chocolate variety that stick to the tips of your fingers. Filled with vanilla or chocolate custard and rolled in crushed nuts or bright rainbow sprinkles, the sandwiches await in the freezer for you to stash away for a rainy day.

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Lake View


This crowded South Loop brunch spot features a menu of— you guessed it—waffles. They offer both popular varieties of Belgian and Liege waffles in savory and sweet combinations, from traditional fruit-topped waffles to waffles benedict. Recently, they’ve turned their “waffle flight” featuring flavors like chocolate, and red velvet and in the past, pumpkin and green tea into an epic assortment of waffle ice cream sandwiches. Our favorite is the red velvet, featuring two waffles around chocolate ice cream blended with discs of white chocolate then topped with a drizzle of chocolate syrup, whipped cream, cherries and rainbow sprinkles. Other variations include a play on bananas foster and a chocolate Nutella concoction. 

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Near South Side