I’ve said this once and I’ll say it again — Chicago is a city for food-lovers. We know good food and we aren’t pretentious about it. Our appreciation for delicious food spans all meals, all styles and all corners of the city. I could spend days and days writing about all my favorite restaurants in Chicago but today, we’re talking about dessert! 

I’m married to a man with a perpetual sweet tooth so over our last 5 years in Chicago, we have discovered some of the best spots in the city for dessert. From ice cream to cakes to doughnuts, Chicago has a delectable assortment of must-try restaurants to indulge a sweet craving. 

These are the Best Places to Satisfy Your Sweet Tooth in Chicago

Cakes, Pies & Pastries

Mindy’s Bakery — 1623 N Damen Ave

When it comes to Chicago’s dessert scene, chef Mindy’s Segal is the queen B. She has been a reigning champ of Chicago sweets for over 15 years. Her iconic Wicker Park restaurant, Hot Chocolate, was probably the most famous dessert place in the city for a decade. Mindy decided to go a new direction in 2020, closing Hot Chocolate and opening up Mindy's Bakery. There is no shortage of delightful sweet treats though! The bakery has a rustic feel with European and farm-to-table influences. There is a morning bake and an afternoon each day. The morning bake has sweets like coffee cake, danishes and chocolate croissants, while the afternoon bake includes cookies and cakes. Keep an eye on their Instagram feed to see what is on the menu, since the options change regularly.

Bang Bang Pie Shop — 2051 N California Avenue

A hole in the wall shop on California Ave, Bang Bang Pie Shop has a seasonal menu of savory and sweet pies. All made from scratch, the creative combinations of flavors range from sweet honey pie to chocolate pecan or even key lime. Get here early (or late) because there is a steady line throughout the morning, especially on the weekend. I tried the sweet honey pie, which was one of the best cheesecakes I’ve ever eaten!

Portillo’s -- 100 W Ontario St

When my cousin got married, she had Portillo’s chocolate cake for her wedding cake. That’s how delicious it is. I’m not even kidding, this chocolate cake is super good. It is rumored that the secret ingredient that makes their cake so moist is mayonnaise. Whatever it is, I love it. I randomly get cravings for Portillo’s chocolate cake and there is one dangerously close to my office. For $4, I don’t think there’s a better way to indulge a chocolate craving!

Spinning J — 100-N California 

This is a hidden gem in Humboldt Park that absolutely kills it on amazing pastry, pies and baked goods. They also happen to have an awesome selection for brunch, which is why you'll also find them on my recommended Chicago brunch guide. Their pies rotate daily, and I've had so many good ones here. The cheesecake is another excellent choice. You can also go for a frozen sweet treat here with their classic shakes and malts.

Ice Cream and Frozen Treats

The Freeze — 2815 W Armitage Ave

If you’re looking for a nostalgia-inducing spot that truly captures the history and diversity of Logan Square, you can’t beat soft-serve purveyor The Freeze. Their shop has been open since the 1950s and it cranks out three flavors of soft serve, which you can order as concretes, dipped cones, shakes or malts. Our favorite thing to order is a “Boston” which is a milkshake topped with a sundae and served with a straw and a spoon so you can simultaneously drink and eat your frozen treat. The endless customizable options are indulgent and delightful, making each visit to this neighborhood icon an adventure. Lines can get long on the weekend, but it always moves fast.

Miko’s Italian Ice — 2236 N Sacramento Ave

There aren’t many accolades or best desserts in Chicago lists where you’ll find Miko’s, but if you ask a Logan Square resident, they will know exactly what you’re talking about. This is another neighborhood favorite of mine! Miko’s offers refreshing fruit flavored Italian ice served out of a walk-up window on a quiet neighborhood corner. I’m a fan of watermelon and mango, but their seasonal flavors are also delicious! 

Pretty Cool -- 2353 N California Ave

Newly opened in Logan Square, the stylishly branded Pretty Cool shouldn’t be missed. This endlessly ‘grammable spot is the real deal! Their creative popsicles are gorgeous, but also taste AMAZING. They’ve got a big variety from creamy pops to chocolate-covered treats to vegan options, offering something for every sweet tooth. One of my favorite flavors recently has been the passionfruit hibiscus truck pop which is lip-puckering and tart.

Black Dog Gelato —859 N. Damen Ave

Inventive flavors and artisanal techniques are on display at Black Dog Gelato. The gelato is made in a classic northern Italian way, with locally produced ingredients like milk, cream, sugar and eggs. Skilled pastry chef Jessica Oloroso helms the menu here, creating truly unique flavors such as goat cheese cashew caramel and strawberry balsamic. Batches are churned each and every day, so you always know the gelato is fresh.

Jeni’s Splendid Ice Creams — 1505 N Milwaukee Street

Regularly rated some of the best ice cream in the US, Jeni’s Splendid Ice Cream uses the best ingredients to guarantee their scoops have a perfect creamy consistency and potent yet creative flavors. Signature flavors include brown butter almond brittle or sun popped corn, but seasonal flavors like brambleberry crisp or lavender blackberry are always delicious too! The sorbets may not be one of their most well-known options, but don’t overlook it. The flavors are tart and smooth offering a more refreshing and light option during warm summer months.

Doughnuts

Stan’s Doughnuts — 1560 N Damen Avenue

If you ride the Blue Line CTA train in the morning, I can almost guarantee that you have smelled the doughnuts from Stan's on your commute. Located just under the Damen CTA Stop, Stan’s Doughnuts offers Chicago's most famous fried treats to make your morning more tolerable. They’ve got a mixed selection, including traditional cake varieties, cream filled, sprinkle topped and berry stuffed. I’m a huge fan of the old fashioned doughnuts, and the lemon pistachio or blueberry are my favorites.

Doughnut Vault — 401 N Franklin St

Tucked in a tiny alley in River North is where you’ll find my favorite doughnuts in Chicago. Doughnut Vault dishes up a daily rotation of artisanal hand-crafted doughnuts in classic as well as modern flavors. I love Doughnut Vault because there is always something different, and old fashioned donuts are the specialty. They only make donuts in small batches so it is common for them to run out of the day’s popular flavor by the early afternoon. If you’re lucky, you might be able to locate their elusive doughnut food truck which occasionally appears at Chicago street festivals.

Do-Rite Donuts — 50 W Randolph 

You can find Do-Rite donuts at hipster coffee shops all around Chicago, or at one of their several locations throughout the city. Do-Rite dishes up classic flavors of various doughnuts styles, cooked to perfection. I am a huge fan of their cinnamon sugar old-fashioned donut, while Sam usually goes for their pistachio lemon cake donut.

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