Food & Drink

The Best Desserts in Chicago

Published On 07/21/2016 Published On 07/21/2016
Green Street Local
Kailley Lindman/Green Street Local

Skillet cookie

Green Street Local

Address and Info

West Loop

Between their molten centers and inevitable scoops of ice cream on top, skillet cookies, by their very nature, are a no-fail hot-meets-cold dessert option. And while any skillet cookie is better than no skillet cookie at all, the drool-inducing iteration at this comfort food-driven bar and lounge has managed to shift from great to irresistible thanks to crushed Heath bar baked into the dough and dusted over a heaping scoop of vanilla ice cream.

Kailley Lindman

Chocolate cake


Address and Info

West Loop

With a lighter, brighter aesthetic and cuisine, and newly minted executive chef Stephen Wambach at the helm, this Randolph St favorite is better than ever, but one important thing has remained constant in spite of so much change: its lauded chocolate layer cake. The fudge-y showstopper boasts layer upon layer of cake, chocolate pudding frosting, and hazelnut praline, and is coated in chocolate ganache and finished with a veritable lava-flow of chocolate glaze.

Anjali Pinto

Brown butter rice crispy treat

Summer House Santa Monica

Address and Info

Lincoln Park

Summer House Santa Monica’s sophisticated twist on the humble rice crispy treat will make you forget every prepackaged variety Mom used to put in your lunchbox. Each bite of the colossal square packs a punch of nutty, buttery flavor, and just enough of a salt factor to keep it from erring on the overly sweet side. Pro tip: to really walk on the wild side, try the chocolate chip cookie studded with brown butter rice crispy treat chunks.

Courtesy of Swift & Sons

S & S Cracker Jack

Swift & Sons

Address and Info

West Loop

No dessert roundup is complete without something sweet crafted by Meg Galus, Chicago’s resident star pastry chef who helms the pastry programs at Michelin-starred BOKA, lauded Momotaro, and steak-centric Swift & Sons. Her perfectly balanced S & S Cracker Jack has been a menu favorite since the steakhouse opened last fall, and features peanut butter mousse, salted caramel, caramel corn, and popcorn sherbet.

Courtesy of XOCO



Address and Info

River North, Wicker Park

Stop by Rick Bayless’ counter-service concept for impossibly airy, sugar and cinnamon-dusted churros that simultaneously satisfy a sweet tooth and leave you hungry for more. Fortunately, three of these bad boys will run you less than $5; for the proper experience, splurge on an optional shot of bean-to-cup chocolate for some always-necessary dipping action.

Courtesy of Maple & Ash

Sundae Service

Maple & Ash

Address and Info

Gold Coast

Forget basic sundaes; at this glitzy steakhouse, pastry chef Aya Fukai presents a table-side sundae service fit for dessert-loving royalty. The interactive setup includes a bowl of house-made vanilla, chocolate, and strawberry ice creams, as well as a tiered tray stacked with an array of accoutrements like salted caramel whipped cream, candied coconut, sprinkles, seasonal fruit, and more for a DIY experience.


Cake Shake


Address and Info

River North, South Loop

The impeccably moist chocolate cake at this Chicago-based hot dog joint is undeniably the chain’s most iconic dessert, but we’re willing to argue that its lesser-known frozen counterpart is actually even better. The creamy concoction features generous chunks of the signature cake blended into a masterfully spun milkshake, and is best teamed with a Chicago dog with all the proper trimmings.

Neil Burger


BomboBar/Bar Siena

Address and Info

West Loop

We don't mean to sound judge-y here, but dining at Bar Siena and not ending your meal with one of its famous bomboloni isn't just wrong; it's sacrilegious. The pillowy, sugar-encrusted Italian doughnuts are stuffed with everything from chocolate to maple buttercream, and are a can't-miss part of dining here. Pro tip: for a bombo fix on the go, swing by the walk-up window around the side of the building and place your order.

Sean Cooley/Thrillist


Bang Bang Pie

Address and Info

Logan Square, Ravenswood

The enticing lineup of pies at this kitschy bakeshop and cafe changes based on the seasonal availability of ingredients, but frequently showcases flavors like chocolate pecan with a maple filling, lemon meringue on a shortbread crust, and coffee custard with vanilla bean cream. Pro tip: pies baked fresh and are available in limited quantities daily; call ahead to reserve a whole pie.

Courtesy of Bar Toma

S’mores pizza

Bar Toma

Address and Info

Gold Coast

This Italian joint backed by Chef Tony Mantuano is known for its wood-fired pizzas, and the dessert-ready s’mores pie is no exception. A thick layer of Nutella coats the restaurant’s browned and bubbly house-made crust, and is crowned with a mass of toasted marshmallows and drizzle of chocolate.

Courtesy of Lowcountry

Deep Fried Oreos


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A delightfully greasy county fair delicacy gets a restaurant-approved twist at this seafood-centric spot oozing with Southern charm. Instead of the usual pancake-like fry batter, these Oreos get dunked in a Rice Krispies cereal dredge before plunging into piping hot oil. The result: a crispy golden exterior that yields a gentle “snap, crackle, pop” with every indulgent bite.

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1. Green Street Local 130 S Green St, Chicago, IL 60607

Watching the big game and stuffing your face full of above-average bar fare need not be mutually exclusive. This sleek sports lounge is equipped with a multitude of TV screens (including a massive projection screen for special events), comfy booth seating, and equally comfy eats ranging from pizzas and a brick of baked pasta aptly named "Carbelicious" to calamari fried in a Captain Crunch cereal batter and an out-of-this-world skillet cookie.

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2. Formento's 925 W Randolph St, Chicago, IL 60607

Executive Chef Stephen Wambach heads up this bright and expansive Italian restaurant. His menu keeps things classic, offering quality dishes like a four-cheese tortellini and a prosciutto-wrapped veal filet. The white tablecloths add to the traditional feel of the space, and collect crumbs from Formento's must-try chocolate layer cake. No, really, try it -- it comes with chocolate pudding frosting and hazelnut praline.

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3. Summer House Santa Monica 1954 N Halsted St, Chicago, IL 60614

From Lettuce Entertain You, Summer House Santa Monica brings Chicago a much-needed dose of SoCal flavor. The restaurant goes full force with its Angeleno theme, from the beach house-meets-garden party decor to the expansive list of California wines. Seafood and vegetable plates shine on the menu -- which also includes tacos, sushi, and burgers -- but the most notable dishes, like wild mushroom enchiladas and king crab orecchiette, are found under the speciality "Things We Love" section. Pro tip: top off your meal with a bacon chocolate chip cookie from the bakery counter at Summer House's sister restaurant, Stella Barra Pizzeria, which is right next door.

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4. Swift & Sons 1000 W. Fulton, Chicago, IL 60607

From Boka Restaurant Group and B. Hospitality, this massive and chic steakhouse in West Loop features a seafood restaurant within the restaurant, stylish design with Midwestern touches, and a menu that includes classic steaks, chilled king crab legs, gold leaf-flecked sundaes. How regal.

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5. XOCO 449 N Clark, Chicago, IL 60654

Conveniently next door to Top Chef master Rick Bayless' upscale Mexican joints Frontera Grill and Topolobampo, XOCO (derived from Mexican slang for "little sister") is a quick-service cafe with communal tables and a central wood burning oven. The aromas of Bayless' take on classic made-to-order south of the border street fare is sure to draw crowds from all over.

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6. Maple & Ash 8 W Maple Street, Chicago, IL 60610

Glitz and glamour come in equal measure at this Gold Coast steakhouse, where heavy fabric is draped from the wooden ceiling and candles rest atop dark tablecloths. The menu here centers around items grilled on a wood-burning hearth, such as a 40oz porterhouse and a 28-day dry-aged strip. Not sure which cut to choose? Tell the waitstaff, "I don't give a f*@ck" -- an actual menu item that results in the chef's choice. And when you're finished, be sure to have Pastry Chef Aya Fukai present you with table-side sundae service.

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7. Portillo's Hot Dogs 100 W Ontario St, Chicago, IL 60654

Local favorite Portillo's specializes in classic Chicago-style hot dogs and an otherworldly chocolate cake that keeps fans coming back for more. They know what they're doing when it comes to hot dogs: the first Portillo's hot dog stand opened in 1963. They also know what they're doing when it comes to chocolate cake: they put it in milkshakes. That's right -- their chocolate cake shake comes blended with generous chunks of the lauded dessert. It's truly a masterpiece.

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8. BomboBar 832 W Randolph St, Chicago, IL 60607

This cute little walk-up window on the side of Bar Siena specializes in plump bombolini and house-made gelato. The cream-filled, hole-less Italian donuts come in flavors ranging from vanilla bean custard and salted caramel to peanut butter and jelly and nutella cream, and luckily, they're served in portions of three, so you don't have to choose just one. The move is to order a few bombolini and a waffle cone filled with two scoops of gelato, but then again, there are gelato cookie sandwiches and insane specials like a Nutella calzone too. Sugar high starts now.

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9. Bang Bang Pie Shop 2051 N California Ave, Chicago, IL 60647

Logan Square's Bang Bang Pie Shop is a reminder of a simpler time, when everyone's favorite neighbor Ethel would let her pies cool on the windowsill. The pies at this bright and buzzy corner bake shop are handmade daily using the freshest seasonal ingredients, and their comforting scent alone will have you floating through the entrance. There are classics like key lime and apple, plus unique recipes like butterscotch meringue and maple bourbon pecan. You won't want to miss the small-batch sour cream biscuits either, which are served with ginger-sage sausage, gravy, a poached egg, and a side of seasonal jam.

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10. Bar Toma 110 E Pearson St, Chicago, IL 60611

James Beard Award-winning Chef Tony Mantuano's Bar Toma in Near North Side is an Italian neighborhood restaurant with open brick walls covered in chalk murals and big leather booths that provide a familial feeling, just like it's classic fare. The mozzarella bar, espresso bar, and gelato are all merely a backdrop to the wood-fired pizzas, the recipe for which Mantuano crafted himself from imported Italian ingredients and are topped with basil, prosciutto, Calabrian chiles, and truffle oil.

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11. Lowcountry 3343 N Clark St, Chicago, IL 60657

Lowcountry in Lakeview serves customizable seafood boils in a Southern and nautical atmosphere with a backyard feel. Buckets of beer are a cheap solution for a big group, and the short-and-sweet roster of specialty cocktails (margaritas and daiquiris), classics and house wine still offer plenty of other options. At 10pm, picnic tables start getting cleared off for beer pong and “bro country.” Downstairs, there are several private karaoke rooms that are available for rent. Experience all of this, but not without ordering a bag -- yes, a bag -- of shrimp, corn, potatoes, and sausage boiled with Cajun spices.