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Amazing Chicago Desserts that You Must Try

The Windy City's sweetest treats.

Got a sweet tooth? Chicago has you covered! We have some of the best ice cream treats, cinnamon rolls, cupcakes, and donuts you've ever tried! Here's where to find the best desserts in Chicago.

an ice cream sundae with whip cream

1 - Lickity Split

This northside ice cream shop is part creamery, part candy shop, and 100% magic. Your inner child will love it! Come for the amazing sundaes and concretes, and stay for the vintage candy store aesthetic! 

They only serve three flavors of custard at a time: vanilla, chocolate, and a rotating specialty flavor. But these three flavors are all you need! You can use these flavors to build your own sundae or concrete from a properly huge selection of toppings. And if you go the sundae route, whipped cream, peanuts, and a cherry are already included in the price! And if you find yourself spoiled for choice, you can choose one of their house specialties.

For a genuine kid in a candy store experience, there’s no better place than Lickity Split.

a purple cupcake in front of the Chicago skyline

2 - Jenivee's Bakery

Cupcakes! Cupcake Glory! Filipino inspired flavors! Trans-owned! Do I really need to keep selling you on this?!?!?

Jenivees is an astounding Chicago dessert shop. You can order specialty cakes and cupcakes, or stop by and choose a treat right out of the case! The flavors they have available on a given day change depending on what they’ve been baking lately, (my personal favorite is the Pink Guava), but they nearly always have their signature Purple Velvet Cupcakes on offer. Purple Velvet is like red velvet cake’s sexy cousin, flavored with ube and stuffed with coconut!

As a heads up, the cafe itself is quite small. There’s a gorgeous patio to use when the weather cooperates, but if it’s not outdoorsy weather, plan to get your cupcakes to go! But go. These cupcakes will change your life.

ice cream scoops with a waffle wedge

3 - Jeni's Ice Creams

Full disclosure, Jeni’s is a global chain and not necessarily a Chicago specialty. But I can’t list my favorite desserts in Chicago without mentioning Jeni’s. And if you don’t have Jeni’s in your city -and they are a major metropolis centric chain- this is your chance!

For me, Jeni’s is the be-all-end-all of ice cream chains. They pride themselves on creative ingredients and unique flavors. They have a long list of amazing classics and regularly changing specialties. And best of all, their “basic” serving includes two flavors and a waffle wedge!

Sample away, but trust me on the salted peanut butter with chocolate chips. It's a shop staple for a reason.

a pastry bag from Stans Donuts

4 - Stans Donuts

This local chain is a staple of Chicago and its resident burbs. To me, they are hands down the best donuts in the city. The donuts are made fresh every day, and come in a variety of creative flavors! I personally love the coconut cake donut, or the pistachio glazed! They also have a long list of coffee drinks on the menu, and some locations also serve gelato in the summer!

Or, if this list of goodies is making your teeth ache and you need something savory, their breakfast sandwiches served on house-made pretzel bagels are a game changer!

5 - Ann Sather's

Friends. It’s time for a story.

In the small town where I grew up, there was a coffee shop. It wasn’t a particularly good coffee shop. The coffee was only ok, and it had the kind of decor that reminded even tiny Andi of their grandmother’s house. This place went out of business when I was a teen. I can’t even remember its name because in my house, we always just called it The Cinnamon Shop.

Because friends. The cinnamon rolls. 

They were huge. Fluffy but not dry. Gooey but not underdone. Perfectly spiced and drenched in frosting that wasn’t sickeningly sweet. There was absolutely no way to eat one without making a huge mess, and that was part of the charm.

I have been searching my entire adult life for a cinnamon roll that comes close to these childhood treats.

The only place that comes close is Ann Sather's.

There are two Ann Sather's locations in Chicago, and both serve their exceptional cinnamon rolls. Truthfully, they serve much more than that. Ann Sather's is a pretty solid Chicago locale for a classic diner breakfast. But the cinnamon rolls are the stars of the show. Try one for tiny Andi. Thanks in advance.

Sample all these Amazing Chicago Desserts!

Whatever your tastes, you can find something to savor in Chicago!

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Love and Shenanigans,


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