Chicago's Cinnamon Roll Bucket List

Forget all about beach body season. Life’s too short not to splurge, especially at brunch, when the order of the day is hangover-healing comfort food. When it comes to sweets, cinnamon rolls are a timeworn staple, and they’re done well all over Chicago. Here are several of the best to check out during brunch. 


Cantina 1910
Cantina 1910

From the churros with roasted cinnamon sugar to the cajeta crumb cake with housemade goat’s milk cajeta, the pastry program at Cantina 1910 is seriously strong. This is especially evident during weekend brunch, when both of those aforementioned pastries shine, along with chile-spiced cinnamon rolls that get generously frosted. 

One of the newest entries to the brunch scene, Dos Urban Cantina has a delicious miscellany of sweets and savories to choose from. Courtesy of adept pastry chef Jennifer Jones, some of the former includes the likes of Mexican chocolate coffee cake, Texas sheet cake, and cinnamon rolls with cream cheese frosting. They’re splendid in their quality simplicity. 

A hybrid between a croissant and a cinnamon roll, new rooftop destination Raised features a brunch pastry called a “Frassant” on their menu. It’s made with croissant dough, cinnamon, sugar, chocolate sauce, and berry jam, and it’s the best of both worlds. 

The cinnamon roll at The Bristol has a bit of a cult following going for it. Which is really saying something, considering the Bucktown restaurant makes so many things well and features a revolving door of seasonal ingredients, house-cured meats, and beautiful preparations. But come brunch and that hulking pastry really stands out, and for good reason. It’s tender and doughy in all the right ways, oozing with cinnamon-sugar goodness and frosting melting down into all the nooks and crannies. 

One can’t talk about cinnamon rolls in Chicago without bowing down to the queen: Ann Sather. The longstanding, famed Swedish breakfast and lunch joint features some of the most renowned cinnamon rolls in the country, and all it takes is one bite to see why. First of all, an order of a single cinnamon roll is actually two conjoined rolls that take up your whole table. They’re ridiculously soft and pillowy, laden with warm royal icing. 

For those looking to up the ante on their cinnamon rolls, head to Yolk and try the unabashedly indulgent cinnamon roll French toast. It’s an enormous plate of sliced and battered cinnamon rolls, with maple syrup rendered entirely unnecessary. Warm and crispy from the griddle, these are brunch pastries on steroids. 

Inspired by everyone’s favorite aromatic mall staple, Little Goat features their own rendition of a Cinnabun on their brunch and pastry menus. True to form, these things are on another level entirely. Sure, they’re just as enormous as that food cart mainstay, but the flavors are intense, potent, and well-balanced, with just the right amount of heady spice to counter all that sweetness. 

- Matt Kirouac