Old Fashioned Buttermilk Cruller at Doughnut Vault: To be fair, you’d be hard-pressed to find a bad donut at this Near North Side pop-up, which offers no indoor seating and has no set hours (doors close as soon as donuts sell out). But if one flavor stands out above the rest, it’s the cake-like old fashioned buttermilk cruller ($2). The buttermilk creates a nice sweet/salt contrast, while the deep-fried outer crust gives the donut a nice crunch.
The Doughnut Vault 400 North Franklin Street, Chicago, Illinois 60654 (map); thedoughnutvault.tumblr.com. Cash only.
Dinkel's Custard Bismark: This Roscoe Village icon will celebrate its 90th anniversary next year, so the bakers in residence have had some time to perfect the art of filled donut making. These bismarks ($1.19) boast cream that is fresh, sweet, and oozy, just the way it should be.
Dinkels' Bakery 3329 North Lincoln Avenue, Chicago, IL 60657 (map); 773-281-7300; dinkels.com
Glazed donut at Old Fashioned Doughnut: Buyers be warned: this place is a schlep to reach. But if you want fresh no-frills, traditional donuts at a reasonable price (most are $1 each), then Old Fashioned Donut is the place to go. Located deep in the South Side, this Roseland spot fries up every type of donut you could imagine right in front of you. The glazed donuts are their specialty, though: not too sweet, but not bland; not gummy or overly airy—just right.
Old Fashioned Doughnut 11248 S. Michigan Avenue, Chicago, IL 60628 (map); 773-995-7420; Cash only.
Chocolate covered donut at Oak Mill Bakery: Oak Mill's chocolate covered donut ($1) is crafted in true European style: made from sweet yeast dough that’s a little spongier, lightly fried, heavy on the chocolate glaze. And with six locations across the city and suburbs, Oak Mill makes accessing these tasty morsels easy.
Oak Mill Bakery For locations, numbers: see oakmillbakery.com.
Raspberry glazed donut at Letizia’s Fiore Bakery : Letizia’s prides itself on using all natural ingredients in its baked goods. Their donuts ($2.50 each) are a bit denser than your typical yeast varietals, but that works in this little Italian-style bakery’s favor. The raspberry glaze packs just enough sweetness to keep things true to form.
Letizia's Fiore 2456 N California Avenue, Chicago, IL 60647 (map); 773-342-4400; superyummy.com
Brioche Donuts at Hot Chocolate : James Beard-nominated pastry chef Mindy Segal’s take on the donut ($11) is more of a dessert than a breakfast item. The brioche makes for a denser, more buttery texture than you’d normally find in traditional donuts. The exterior has a nice crunch, and when dipped in the accompanying chocolate fudge, these already delicious goodies become even more delectable.
Hot Chocolate 1747 N. Damen Avenue, Chicago, IL 60647 (map); 773-489-1747; Hot Chocolate
Sprinkled vegan donut (and hole!) at Fritz Pastry: Fritz Pastry gives you the whole donut—hole included. For those of you with an extra sweet tooth (and vegan restrictions), we recommend the rainbow sprinkle donut ($2). The dough and frosting are made with soymilk—don't knock it 'til you've tried it.
Fritz Pastry 1408 W Diversey Parkway, Chicago, IL 60614 (map); 773-857-2989
Chocolate Bavarian cream at Rolling Donut: Nestled inside a tiny strip mall off of busy Ashland Avenue, Rolling Donut is easy to miss. All the better for those who regularly patronize this establishment. Though Rolling Donut serves more than 15 varieties of donuts, our favorite is the Chocolate Bavarian cream ($1). The donut itself is very light, allowing the cream to permeate its doughy layers, while the chocolate drizzle is laid on thick.
Rolling Donut 3170 S Ashland Avenue, Chicago, IL 60608 (map); 773-376-5757