When I recently told somebody I lived in Chicago’s Logan Square in 1999, they told me I was a pioneer. There were a few liquor stores that didn’t even bother to check my fake ID, a Gap I never went to, and a Dunkin’ Donuts. Yet somehow, between 2002 and 2016, Chicago ended up becoming the doughnut capital of the country. Now there are people in yoga clothes walking around, boutiques, and the Michelin-starred Longman and Eagle, a place commonly mentioned among the best restaurants in the entire country. It’s a place where you can sample any of the 300 whiskeys from all over, eat the duck hash (you must eat the duck hash), and if you can nab one, go upstairs to one of the couple of hotel rooms on the premises. It’s really a perfect place any time of the week, but it’s even a little bit better on the weekend when the Off Site Bar (OSB) transforms into the OSB Donut Shop, a Chicago doughnut mecca headed up by pastry chef Jeremy Brutzkus each Saturday and Sunday. 

On the day I showed up, an Earl Grey old-fashioned honey-glazed, lemon curd-filled, rhubarb-glazed, and a chocolate-chip fritter all showed up at my table on a wooden board like a flight of beer or whiskey. Since I read in high school that Dante saw a circle of hell reserved for the wasteful, I felt it my duty to eat each one. The Earl Grey tasted almost like a high-class Cinnabon (seriously the highest compliment I can give something) and didn’t fall apart in my coffee, and the fritter was almost like a babka. The only disappointment was that the next morning I checked the Longman and Eagle Instagram and they were serving up bourbon doughnut holes. Why did I pick Saturday instead of Sunday? Will I live with that shame forever?

This is the thing about going on a doughnut tour of any city, but is especially true of Chicago doughnut shops: You are killing yourself. I can’t go to Chicago and not get a hot dog or an Italian beef or both. I eat a ton of meat, and I drink a lot of beer and whiskey. Then, to top it off, on this trip I digested a ton of doughnuts. Thankfully I know enough people in the city to help me out, but the combined total of doughnuts I ate is pretty staggering. 

Even just including the ones I ate at the small River North Glazed and Infused—a mini-chain with five locations scattered throughout the city, mostly for take-out—probably put me over my average yearly doughnut consumption. I considered walking up to the take-out window, hopping in a cab, and going on my way, but figured I’d check out the store itself, which was packed with Chicago doughnut aficionados. Glazed and Infused focuses on just doughnuts, and there is no such thing as a tiny doughnut there. (That’s not including the Homer Simpson dream jumbo doughnut you can get customized for $35.) The Pilsen doughnut, which is firm but not too dense, knocked me and my friends on our asses, with the little hints of spice provided by the mango-pineapple glaze topped with chili pepper that’s cut into by the lime zest, but it was the Maple Bacon Long John that put the fear of the lord into me. All my Hebrew school teaching couldn’t keep me from taking a bite of that monster, which I swear is the size of a human femur bone and topped with a crispy strip of bacon. “Why would anybody do something like this?” I asked as I took another bite, then another. 

Right up the road, also in the River North neighborhood, is the Doughnut Vault. I think about what a classy name it is, and like to imagine the backstory of the place starts with a few old-timey gangsters breaking into a vault with the ideas they were going to find millions of dollars, only they found a ton of delicious doughnuts filled with seasonal fruits. Of course, that didn’t happen, but the priceless pastries you can pick up there are world-class, and the coffee, served up by local roaster Metropolis, makes Doughnut Vault possibly the best place to go in if you want to consider doughnuts and coffee a full breakfast. The buttermilk old-fashioned and glazed chestnut are the big winners, but the trick is to try and get that combo for just two bucks (cash only). Even the plain old cake doughnuts are better than anything you’ve had anywhere else, fluffy and perfect.

This is the thing about going on a doughnut tour of any city, but is especially true of Chicago doughnut shops: You are killing yourself.

I probably should mention that Do-Rite Donuts in the Loop has a fried-chicken sandwich called the Sweet Heat that they served on a sliced glazed doughnut. I’m sure if you get there at just the right time you can get one and consider it breakfast. With wood paneling on the walls and a black changeable letter board with white Helvetica letters that tells you the daily specials, Do-Rite pays tribute to old-school coffee-and-doughnut spots, but is totally modern. The vanilla bean and cinnamon crunch-glazed is pretty hard to beat, but the pistachio and lemon is also unbelievably great. “I think the real reason for the amount of great doughnut places in Chicago was [that] a cumulation of a lot of talented people started to create golden circles of goodness around the same time,” owner Jeff Mahin tells me. “The city all of a sudden had a variety of great doughnut options and it sparked a giant match.”

 

Dat Donut is the king of Chicago doughnuts on the South Side. Open 24-7, the thing about Dat Donut is you don’t really need to do a lot of thinking; you just get a dozen for under $10. You get a couple of glazed bowties, a few caramels, maybe some chocolate, and about five or six of the buttermilk cake doughnuts, because good lord are those delicious. Why don’t more people offer up buttermilk doughnuts?, I wondered to myself as I pulled out and headed to Valois for a plate of steak and eggs. By the time I made my way back to my hotel in the Loop, filled with my breakfast and about four doughnuts, I saw something that I was dreading: Beaver’s.

A mad doughnut scientist on wheels, Beaver’s is a food truck that rolls across the city offering up fried-to-order doughnuts with toppings like marshmallows with Rice Krispies, banana, and Nutella, and the one I got: chocolate sauce and peanut butter. I got into my car, took a bite, and put my head back like in that picture of Ben Affleck vaping alone in his car. A moment of calm with a hint of underlying sadness, me wondering what the hell was I doing with my life, remembering that my family history makes me at risk for diabetes, but still so damn happy that I’d had so many doughnuts in such a short period of time. I can’t quite say I understand what competitive eaters feel like when they win a contest, but after downing so many doughnuts in the name of trying to better understand why Chicago, the city of my birth, does them better than anywhere else. Here’s what I could come up with, and it’s something I came up with in the unlikeliest of places: a Dunkin’ Donuts parking lot in the suburbs.

The doughnut (or donut, if you want to spell it that way) is a far more versatile food than we give it credit for. Think about the times of the day you’ve had one, and you could probably point to any hour on the clock, a.m. or p.m. Some places bring them to your table as a complimentary dessert after dinner. But most likely you find yourself ordering one early in the morning when you don’t have time for pancakes, but also would rather add on the calories than get the supposed “low fat” blueberry muffin that looks suspiciously like the regular one. Yet doughnuts have been taken for granted for far too long. 

Places think they can top them with whatever kind of sugary frosting they want and that’s it, that’s all they need to do. The thing you get that ties all the doughnuts I had over a weekend in Chicago was nuance—that, and the good old Midwestern taking pride in your work thing that people love to talk about. You can tell that the doughnuts at every place I went to took time to make, and, unlike the Dunkin’ I visited for coffee and to use the bathroom (the former a means to get to the latter since I always worry about using a bathroom without buying anything), there’s a connection to the doughnuts. The doughnuts come first. While Dunkin’ and Krispy Kreme (all due respect to my favorite southern doughnut chain) have come up with new sugar-loaded coffee drinks to boost sales, doughnuts were the number-one priority at every single place I visited in my hometown. And that’s why Chicago, a town that tends to look over the first meal of the day, and where an egg-and-cheese bagel is scarce on the ground, does doughnuts better than anywhere else.