Chicago is a food city in every sense of the term : we have Michelin - starred and James Beard Award - winning restaurants and chef , a vast and ever - develop dining scene , and local anaesthetic who will turbulently reason that no one does pizza pie or live dogs like we do . And yet , if there ’s one microcosm of our intellectual nourishment - fueled identity element that ’s sadly underappreciated , it ’s the dessert - y detail that we bring to the mesa . To remedy that , we ’re radiate the spotlight on 11 of Chicago ’s sweetest indulgences .
Skillet cookie
Green Street Local
Between their liquefied center and inevitable scoops of ice cream on top , frying pan cookies , by their very nature , are a no - fail hot - meets - cold dessert option . And while any frying pan biscuit is better than no skillet cookie at all , the drool - inducing iteration at this comfort food - aim measure and couch has manage to shift from smashing to resistless thanks to crushed Heath bar bake into the simoleons and dust over a heaping scoop of vanilla ice cream .
Chocolate cake
Formento’s
With a unclouded , brighter esthetic and cuisine , and newly minted executive chef Stephen Wambach at the helm , this Randolph St front-runner is better than ever , but one crucial thing has rest constant in spite of so much change : its extol chocolate level patty . The fudge - y show-stopper swash level upon layer of patty , chocolate pud frost , and hazelnut praline , and is coated in chocolate ganache and finished with a authentic lava - flow of chocolate glaze .
Brown butter rice crispy treat
Summer House Santa Monica
Summer House Santa Monica ’s sophisticated twist on the menial rice crispy treat will make you bury every prepacked variety Mom used to put in your lunchbox . Each pungency of the colossal square packs a puncher of nutty , buttery flavor , and just enough of a salt factor to keep it from erring on the excessively sweet side . Pro pourboire : to really walk on the raging side , try the chocolate cow chip biscuit studded with browned butter Elmer Rice crispy treat chunks .
S & S Cracker Jack
Swift & Sons
No sweet roundup is everlasting without something sweet crafted by Meg Galus , Chicago ’s resident star pastry chef who helms the pastry program at Michelin - starredBOKA , laudedMomotaro , and steak - centric Swift & Sons . Her dead balanced S & S Cracker Jack has been a fare preferred since the chophouse unfold last free fall , and feature peanut butter mousse , salted caramel , caramel corn , and popcorn sherbert .
Churros
XOCO
Stop by Rick Bayless ’ counter - service concept for impossibly aeriform , wampum and cinnamon - dot churros that at the same time fulfil a sweet tooth and leave you athirst 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 hot chocolate for some always - necessary dipping action .
Sundae Service
Maple & Ash
blank out basic sundaes ; at this glitzy steakhouse , pastry dough chef Aya Fukai presents a mesa - side ice-cream sundae table service fit for sweet - enjoy royalty . The interactive frame-up include a bowl of house - made vanilla , chocolate , and strawberry ice creams , as well as a tiered tray stack with an array of accessory like salted caramel rack up cream , candied coconut , scattering , seasonal yield , and more for a DIY experience .
Cake Shake
Portillo’s
The impeccably moist umber cake at this Chicago - establish spicy hotdog joint is undeniably the mountain range ’s most iconic sweet , but we ’re uncoerced to argue that its lesser - known frosty counterpart is in reality even better . The creamy mixture features generous chunks of the signature cake merge into a masterfully whirl milk shake , and is best teamed with a Chicago cad with all the right trimming .
Bomboloni
BomboBar/Bar Siena
We do n’t entail to sound judge - y here , but dining at Bar Siena and not ending your meal with one of its famous bomboloni is n’t just wrong ; it ’s sacrilegious . The pillowy , sugar - encrust 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 repair on the go , swing by the walk - up window around the side of the construction and place your order .
Pie
Bang Bang Pie
The enticing lineup of Proto-Indo European at this slushy bakeshop and cafe change based on the seasonal availability of ingredients , but frequently showcases relish like chocolate pecan with a maple pick , maize meringue on a shortbread gall , and umber custard with vanilla noodle pick . Pro tip : pies baked novel and are available in modified measure daily ; call before to reserve a whole Proto-Indo European .
S’mores pizza
Bar Toma
This Italian reefer backed by Chef Tony Mantuano is have it off for its wood - fired pizzas , and the dessert - ready s’mores Proto-Indo European is no exception . A thick layer of Nutella coats the restaurant ’s browned and bubbly sign of the zodiac - made impertinence , and is crowned with a mass of toasted marshmallows and drizzle of chocolate .
Deep Fried Oreos
Lowcountry
A delightfully oily county just delicacy gets a restaurant - approve crook at this seafood - centric blot oozing with Southern charm . Instead of the usual pancake - alike fry batter , these Oreos get souse in a Rice Krispies cereal grass dredge before plunge into mop up hot crude . The result : a crispy golden outside that give in a gentle “ snap , crackle , bulge ” with every lenient bite .
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Kailley Lindman/Green Street Local
Kailley Lindman
Anjali Pinto
Courtesy of Swift & Sons
Courtesy of XOCO
Courtesy of Maple & Ash
Portillo’s
Neil Burger
Sean Cooley/Thrillist
Courtesy of Bar Toma
Courtesy of Lowcountry
