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9 Chicago Eateries with Delicious Desserts You Need to Try

Written by Dave Odegard

This blog post was updated on December 24, 2019.

When it comes to cuisine, Chicago doesn’t really have the reputation of a food scene featuring desirable desserts. Thick pizza you need a knife and fork to eat? Oh, yeah. A hot dog style PACKED with toppings? Yep. Popcorn? Of course. But sweet treats? Eh….

However, just because a city isn’t well known for something, doesn’t mean the place is devoid of it or doesn’t do it well. Case in point: the Windy City and its desserts. Because while they may not be famous outside of Illinois, Chicago has plenty of eateries with delicious desserts that you need to try.

Here are just 9 places in Chicago with the divine treats and dishes you should order:


Chocolate Doughnuts

A walk-up window on the West Loop neighborhood Bar Siena, Bombo Bar is perfect for a late-night treat. And although they serve gelato, Italian ice, and coffee, the must-order that every visitor has to get is the bomboloni — essentially an Italian donut covered in sugar and stuffed with the customer’s choice of delicious filling.

The Original Rainbow Cone


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A Chicago summer icon, the Original Rainbow Cone was started by Joseph Sapp in 1926 and soon became famous throughout the city for its signature ice cream cone stacked with different flavors. Today, the business is still owned by members of the Sapp family and you can order a cone piled with chocolate, strawberry, Palmer House (vanilla with cherries and walnuts), pistachio, and orange sherbet ice cream at the original Southside location. But visitors should be aware that the Original Rainbow Cone is only open seasonally. So if you’re looking for some rainbow cone goodness, you’ll want to book flights to Chicago between March and November.

Maple & Ash

Vanilla Ice Cream

The Gold Coast area steakhouse Maple & Ash is often described as “elegant” and “glamorous” and it’s known for not taking itself too seriously (the chefs-choice option is listed on the menu as “I don’t give a f*@k”). So it makes sense that their must-order dessert would be an almost sarcastic royal-take on an ice cream sundae via a bowl of house-made ice creams served with a tiered tray of toppings for customers to put on themselves.


Strawberry Dessert

A gastropub with a coveted Michelin star, Dusek’s is part of the recent revitalization of Thalia Hall, a Pilsen landmark that was built in 1892 by local businessman John Dusek (hence the bar’s name) and served as a multi-purpose performance, bar/restaurant, and retail space until it was shuttered in the 1960s. Two go-to desserts on the menu include the chocolate pecan tart and the tres leches panna cotta.

You may also enjoy: 10 Unique Chicago Spots You Have to Visit

Cone Gourmet

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Opened by Irish immigrant Sean McGuire in 2013, Cone Gourmet in West Loop is considered by many to be the best ice cream shop in the city. And a lot of those same people consider the blue Cookie Monster, which includes Oreo and cookie dough, to be their signature ice cream.



Inspired by, and taking its name from, the “backwaters take on the modern-day donut” that founder Karen Fox’s grandfather made for loggers in northern Wisconsin during the 1930s, Firecakes is pretty much a Chicago institution with four locations throughout the city and a food truck. If you find yourself near a Firecakes, be sure to try to their ice cream doughnut sandwich, which is exactly what it sounds like: a donut cut in half with ice cream in between. You just have to choose between the featured sandwich of the month (which changes each month) and the Classic (made with a honey glazed donut, vanilla ice cream, and a chocolate sauce). Although no one will judge you for ordering both.


Chocolate Cake

Although it’s only a couple of years old, Formento’s in West Loop has already become famous throughout the Chicago foodie scene for its modern take on the classic Italian restaurant. It’s also famous for its chocolate cake, so be sure to order a slice at the end of your meal.

Mindy’s HotChocolate

Hot Cocoa

Founded by the award-winning (and famously tough) pastry chef Mindy Segal, Mindy’s HotChocolate in Bucktown is the perfect place to warm up during the cold Chicago winter with a mug of (you guessed it) hot chocolate, of which there are nine flavors to choose from (but marshmallows come with all of them). And it’s best to pair that hot chocolate goodness with an order of donuts.



Celebrity chef Rick Bayless’s Xoco in River North is known for two things: offering his famously delicious take on Mexican food in a laid-back atmosphere and having the best churros in Chicago. Don’t listen to anyone else claiming another Chi-town establishment does the traditional crispy fried Mexican treat any better!

Know of any other Chicago dessert spots? Let us know about it in the comments below! 

About the author

Dave Odegard

Dave Odegard is an ex-army brat turned internet word person, whose work has been published on Maxim Online, USAToday, Buzzfeed, and more. He is currently the Senior Content Writer at Fareportal (CheapOair's parent company) and spends his free time exploring the wilds of Brooklyn, New Jersey, and Sweden.

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