The butterscotch old fashioned at this tiny Loop shop is the absolute best doughnut you will ever put in your mouth: crunchy raised edges, an ethereally light cake center, and a barely there butterscotch glaze. If it’s not available (doughnuts are made with such care that shelves empty more quickly than they can be refilled), the pistachio-Meyer lemon cake option and vanilla-bean yeast version rolled in cinnamon streusel are still better than 99% of doughnuts in town.
Do-Rite Donuts, 50 West Randolph St (at Dearborn); 312-488-2483.
Dinkel’s gets bragging rights to being about 90 years ahead of the doughnut trend: The Lakeview bakery has been frying up ringed beauties since 1922. There’s a $10 credit-card minimum, which is all the more reason to buy a dozen. The Boston crèmes ooze with thick, sweet custard, the sour cream old-fashioneds have just a hint of tang, and the cinnamon doughnuts — our fave! — are a glitter bomb of granulated sugar, only way less annoying to clean up.
Dinkel’s Bakery, 3329 N Lincoln Avenue (at Henderson Street); 773-281-7300.
Heralded as a doughnut visionary for his decadent bacon-butterscotch version at Pilsen’s Nightwood, Enoch Simpson finally has his own restaurant in Roscoe Village. Although it’s been three years since he left Nightwood, it looks like Simpson’s still got doughnut mojo. The bacon-butterscotch returns, along with flavors like Nutella milk stout.
Endgrain,1851 West Addison Street (at Wolcott); 773-687-8191.
The original Munchkin: bomboloni, golf-ball-sized doughnuts served as a traditional dessert or snack in Italy. Many are stuffed with fruit or custard, but this restaurant at the Radisson Blu opts for an unfilled version paired with three thick, decadent dipping sauces: salted caramel, rhubarb, and white chocolate. Cozy up to the bar for an order and a cocktail: On our calendar, every day is National Cocktail Day.
Filini, 221 North Columbus Drive (at South Water Street); 312-477-0234.
We have to thank Fête Night Market for our first taste of Firecakes, and the new doughnut mecca’s central Hubbard Street location for many more since then. Tasting notes: 1) Who knew jelly filling could be tart, tangy, and not a creepy shade of electric red? 2) THE APPLE FRITTER IS AS BIG AS A FRISBEE. We’re exaggerating. But seriously. 3) If you’re gearing up for “I can’t believe I ate the whole thing” remorse, the maple-glazed pineapple and bacon is such a cute little peanut of a doughnut that we maintain it doesn’t count.
Firecakes, 68 West Hubbard Street (at Dearborn); 312-329-6500.
Glazed & Infused
Here’s the problem with Glazed & Infused: with locations in Lincoln Park, Wicker Park, the West Loop and Streeterville, you’re always walking by one. And if you’re walking by one, you will go in. And if you go in, you will get a banana cake doughnut with cream-cheese frosting. And if you get a banana cake doughnut with cream-cheese frosting, you will spot the yeast doughnut topped with pretzels, potato chips, and caramel. And if you spot the yeast doughnut topped with pretzels, potato chips, and caramel… Suddenly, the book If You Give a Mouse a Cookie makes a lot more sense.
Glazed & Infused, multiple locations.
Even after the departure of Enoch Simpson (see: Endgrain), the bacon-butterscotch doughnut at Nightwood’s Sunday brunch gets all the love — from food writers, from enchanted patrons, from our mom (we’re not jealous or anything). But don’t overlook the second doughnut on the menu. Right now, it’s a vanilla-custard-filled vixen with a chai glaze and shortbread crumbles, and it’s so good it may just steal golden child status from its bacon-laden older sib.
Nightwood, 2119 S Halsted Street (at 21st); 312-526-3385.
Siena Tavern Bomboloni meet booze at Siena, where a paper bag of the doughnuts comes with cute miniature squeeze bottles of whiskey caramel and raspberry chianti sauces. But you could pop these warm, airy treats sans sauce and still be 100% satisfied. We think even Florence-born chef/owner Fabio Viviani’s grandmother would approve.
Siena Tavern, 51 West Kinzie Street (at Dearborn); 312-595-1322.
You can’t get a cronut in Chicago, but you can get a pronut, the name we’re giving to chef Tom Van Lente’s pretzel-doughnut hybrid. The small, fried balls of pretzel dough with a hint of chocolate in the center are tossed in cinnamon sugar and served with a coffee mug of rich drinking chocolate that poses an important question — dip or sip? We say both.
Two Restaurant,1132 West Grand Avenue (at May Street); 312-624-8363.
Photo: Courtesy of Do-Rite Donuts