Chicago's Best Places for Sweet Treats

Favorite Chicago spots to find all the sugary goodness you crave, including cookies, pies, candy and more.

Chicago has its iconic food items (deep dish and hot dogs, for example), but sweets don't quite rank at the top. Still, there are a few that come close: Frango mints of the late, great Marshall Field's department store; anything at Fannie May candy shops, which opened in Chicago in 1920; or possibly Lemonheads, which were introduced in 1962 by the Chicago-based Ferrara Candy Co.

Those certainly have their fans—and history, to boot—but we decided to pick some of our own favorite sweet spots. It was hard to choose just a few cavity-inducing cravings, so instead web rounded them up into 10 delicious categories. Whether you have an insatiable sweet tooth or just want to bring some Chicago gifts home with you, the city has an abundance of sugary goodness.

Candyality candy bins

Candies

Lucky us, we have shops in town that carry the complete candy rainbow. Dylan’s Candy Bar is the nationally recognized name. Founded by Ralph Lauren’s daughter, the store shows off her talent for design, her flare for style and her love of candy (there are 7,000 different types here). Try a candy cocktail at the café. A personality analysis is available with purchases at Candyality, an indie sweet boutique owned by native Chicagoan Terese McDonald. Windy City Sweets is a local pick, a mainstay in East Lakeview since 1983.

Pies

A passion for social justice led former Lettuce Entertain You chef Mary Ellen Diaz to open First Slice Pie Café. She created a subscription program that provides three meals a week to subscribers—pie for dessert, of course—and helps fund nearly 4,000 meals a month to Chicago’s hungry. We feel extra-good about eating some of the most memorable pies we’ve ever tasted, including the pie of our dreams, the French silk. Equaling the deliciousness is Hoosier Mama Pie Co., a charming retro café whose Friday Night Flights of three small slices is a perfect sampler of whatever’s on tap: maybe apple, chocolate chess or the ginger custard.

Katherine Anne Confections

Chocolate

Catch the scent of chocolate in the Chicago air? It’s from the Blommer Chocolate Co., founded in 1939 and selling its products at a discount in the attached retail store. Vosges Haut-Chocolat kicked off the exotic-chocolate craze in the city and has expanded astronomically. Search by preference: dark, milk and white, but also beer, salt and flowers. We adore Katherine Anne’s Confections for her in-store-made truffles like the Manhattan cocktail, goat cheese walnut and toasted coconut rum. Though a California transplant, Lolli and Pops earns a spot for its artistic edible creations, beautifully presented.

Cookies/Macarons

When it comes to cookies, we’re pretty picky. Which is why Beatrix gets top billing here. The magic cookie gets raves, as does the triple chocolate. Pair it with a local brew of the day like Nitro Coffee. At multi-award-winning Alliance Patisserie, the window display of stunningly decorated cakes will draw you in, but the exquisite French macarons will keep you coming back. 

Hot Chocolate

When the weather outside is frightful, there is nothing more delightful than a mug of hot cocoa. But store-bought packets just don’t cut it when we have Ghirardelli Chocolate. Get the classic or try the sea salt caramel. With a name like Mindy’s HotChocolate, the hot chocolate ought to be good. And celebrated chef Mindy Segal does not disappoint. There are nine types, all served with house-made marshmallows. The Black and Tan is literally a third hot fudge. For a true Mexican hot cocoa, made from cacao beans ground and roasted on site, head to Rick Bayless’s Xoxo.

Doughnuts

Real doughnut lovers know the baked goods are not just for breakfast time, and with so many creative choices, it’s easy to pack up a dozen (and eat most by yourself). Pick up the pint-sized maple-glazed pineapple & bacon at Firecakes—trust us, the flavors work perfectly together. Looking for something more traditional? Hit up the rapidly expanding Stan’s Donuts & Coffee, with locations throughout the city.

RPM Steak chocolate cake

Cupcakes/Cakes

So, cupcakes are pretty popular, to say the least. But we definitely can’t forget about the OG classic cakes either. For an individual bite, check out Molly’s Cupcakes—we’re all about the center-filled flavors, like the Cookie Monster with a cookie dough surprise or the peanut butter-y Ron Bennington. And you definitely can’t go wrong with a beautiful classic cake from New York-import Magnolia Bakery, decked in the signature pastel buttercream frosting.

Pastries

Pastries, pastries, pastries—where do we even begin? For these sweet treats, we like to take a trip around the world in our diverse city. Our itinerary consists of French petit fours from Vanille Patisserie, then a trip to Chinatown for egg tarts from the famous Chiu Quon Bakery, delightfully finished off with a true cannoli from Scafuri Bakery in (where else?) Little Italy.

Restaurant Desserts

When there are desserts this great on the menu, you better make sure to leave room to cap off your meal. It was a tough decision, but some of our favorites include the glamorous, gilded 14K chocolate cake at RPM Steak, the salted caramel and chocolate cheesecake that made our eyes roll back in our heads at The Hampton Social, any of the pieces of art that are the desserts at the impeccable North Pond, and the go-to classic 12-layer cake at Harry Caray’s Italian Steakhouse.

Ice Cream/Gelato

Everyone in Chicago screams for ice cream—and its yummy Italian cousin, gelato. We’re in love with the fresh, consistently rotating gelato at Paciugo, and with three flavors just in the smallest “piccolo” cup, it’s easy to try a bunch at once. For a big old cone of ice cream, head to city-favorite The Original Rainbow Cone, open since 1926, or for an Irish twist, check out Cone Gourmet Ice Cream for the Shamrock, a soft serve cone covered with Lucky Charms.

 

Sarah Perkins
About the author

Even though she grew up in a small suburb north of Chicago, Sarah knew she was meant for somewhere bigger, more excit...