13 Mouthwatering Chicago Desserts to Satisfy Your Sweet Tooth

Whether it’s the middle of winter and you’re in need of some inventive hot cocoa, or you’re sweating it out in the midst of summer, just dying for a rainbow ice cream cone, here are all of the best desserts you can find in and around Chicago.

Photo Credit: Firecakes Donuts Facebook

Cake Donuts @ Firecake Donuts

205 W Wacker Dr, Chicago, IL 60606 | 68 W Hubbard St, Chicago, IL 60654 | 2453 N Clark St, Chicago, IL 60614


Firecakes offers by far one of the best desserts in Chicago. It’s exactly what it sounds like: a deliciously massive pile of double-stacked dough, shaped like a birthday cake and smothered in sprinkles and frosting. Yum. Don’t feel like getting off the couch? We feel you. Order their donuts for delivery and skip changing out of your pajamas.

Bang Bang Pie & Biscuits
Photo Credit: Bang Bang Pie Facebook

Key Lime Pie @ Bang Bang Pie & Biscuits 

2051 N California Ave, Chicago, IL 60647 | 4947 N Damen Ave, Chicago, IL 60625


Skip to Bang Bang Pie & Biscuits and enjoy their all-time classic Key Lime Pie, which is a key lime custard with lime zest, whipped cream, and yummy graham crust. Classics never let anyone down… that’s why they’re classics. Right now their physical locations are closed, but check their website tomorrow to order pickup from their pantry.

Garrett's Popcorn
Photo Credit: Garret Popcorn Shops Facebook

Chicago-Style Popcorn @ Garret Popcorn

Multiple Locations


Not only can we lay claim to the sweet, delectable mix of caramel and cheese popcorn that comes in the Garret Mix as Chicagoans, but we also don’t hesitate to indulge in our original dessert, no matter what season we’re in.

Read More: The Best Fast Food Desserts: Root Beer Floats, Cookies, & Cakes

Rainbow Cone
Photo Credit: Original Rainbow Cone Facebook

Rainbow Cone @ Original Rainbow Cone

9233 S. Western Avenue, Chicago, Illinois 60643

Yes, indeed, Chicago was the very first to pile Orange Sherbert, Pistachio, Palmer House, Strawberry, and Chocolate ice cream onto a waffle cone for the world to enjoy. And boy, are we grateful. Rainbow Cone is one of the most interesting and best dessert places in Chicago. As the heat picks up, we’re grateful that they’re open for pick-up and carry-out!


Photo Credit: Old Town School of Folk Music

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Photo Credit: BomboBar

Cooler Chocolates @ BomboBar

832 W Randolph, Chicago IL, 60607

These hot chocolate concoctions from BomboBar are one of the best desserts in ChicagoChoose between S’mores and Party Monster (if you can) and you’ll be sippin’ on dessert heaven before you know it. While the Old Town location is currently closed, the West Loop location’s walk-up window is ready for your order!

Sugar Bliss Cake Boutique
Photo Credit: Sugar Bliss Cake Boutique

Frosting Shot @ Sugar Bliss

115 N. Wabash, Chicago, IL 60602

For just a dollar, you can get a shot-sized portion of frosting to give your taste buds that extra kick. This fancy dessert destination in Chicago offers an extensive list of deliciousness to fill your cup and down that baby like a champ. 

Read More: 5 Popular Chicago Architects to Be Familiar With

Photo Credit: Portillo’s Hot Dogs Instagram

Chocolate Cake Shake @ Portillo’s

100 W. Ontario, Chicago IL 60610 | 520 W. Taylor St, Chicago IL 60607

The Chocolate Cake Shake from Portillo’s is one of our favorite desserts in Chicago, and this couldn’t be a list of Windy City desserts without it. It’s a classic. Don’t you forget your roots.

Churro Factory
Photo Credit: Churro Factory

Churro Fiesta @ Xurro Factory

Multiple Locations

The Xurro Factory offers one of the best desserts in Chicago. A foot-long churro doused in whipped cream, chocolate syrup, and sprinkles await your taste buds. Gonna be honest, I’m not sure why churro is spelled with an “x” on their website, but that’s okay. We love these desserts anyway! And with Navy Pier reopened, you can grab one of their amazing churros from their Navy Pier location.

The Little Goat Diner
Photo Credit: Little Goat Diner Instagram

Choco Taco Sundae @ Little Goat Diner

820 W Randolph St, Chicago, IL 60607

Those little choco tacos you had from an ice cream truck at camp all those years ago got an upgrade at the Little Goat. This massive dessert boat is enough to serve you and all your friends, but we won’t judge you if you just want to eat it all yourself.


Photo Credit: Floriole Facebook

Pineapple Upside-Down Cake @ Floriole

1220 W Webster Ave, Chicago, IL 60614

Okay, so I know upside-down cake is like a classic fav and not original at all but just wait until you taste Floriole’s version. Now both aesthetically pleasing and absolutely delicious, Floriole managed to completely upgrade an age-old recipe. Currently, they’re publishing menus on their online store while the physical location remains closed. The drop happens on Friday evenings, so check it out tonight!

Gyu Kaku
Photo Credit: Gyu-Kaku Japanese BBQ Facebook

Lady M Crepes @ Gyu-Kaku Japanese

Multiple Locations

A delicious scoop of green tea ice cream next to a towering stack green tea-flavored crepes…. what more could you want? While dine-in isn’t being offered at their Chicago locations, take-out and delivery are both available. What are you waiting for?

Read More: 7 Best Wine Stores in Chicago

Insomnia Cookies
Photo Credit: Insomnia Cookies Facebook

Cookiewich @ Insomnia Cookies

Multiple Locations

Cookie fiends rejoice. Insomnia Cookies offers fancy dessert options for cookie fanatics. Insomnia puts a spin on the classic ice cream sandwich by letting you choose which cookies serve as the buns and which flavor will fill the middle. Contrary to popular belief, this dessert place in Chicago doesn’t cure insomnia… it induces it with all that sugar.

Nothing Bundt Cakes
Photo Credit: Nothing Bundt Cakes

Bundtinis @ Nothing Bundt Cakes

Multiple Locations

These fun bite-sized bundtinis are deliciously grand in flavor. A great treat for gatherings, or you know, just for yourself. Online orders are now available!

Restaurant Closures Chicago

Restaurant Closures to Increase During the Winter Season

The COVID-19 health crisis may force restaurants in the city to shut down for the winter season.

Restaurant Closures Set to Increase

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Featured Image Credit: BomboBar