I am just going to start with our ultimate favorite, because if you're not going to make it to the end of this post, you should just know that the best yeast doughnuts in all of Chicago comes from a little hotspot (punnnn!) called Firecakes. No one in Chicago that we talked to over the weekend seems to have heard of this place, which is a sad, crying (no - bawling!) shame.
Inside, the doughnut was filled to the brim with a caramelicious filling - surprisingly not too sweet and perfectly paired with the crunchy icing. Good start.
My boring heart always falls for the traditional glazed (call me a doughnut purist!) and this one was heaven-sent! Absolutely light, wonderfully glazed and simply melts upon the tongue. Utter perfection.
We also tried the lemon and bacon pineapple.
Completely solid little numbers also with plentiful filling, much to Diana's delight!
So we dutifully went back the next afternoon.
The ice cream sandwiches are made to order using glazed doughnut buns, a rectangular slab of ice cream that fits perfectly between the buns, and a good healthy drizzle of hand-squeezed hot fudge.
Contrary to the travesty of cookie ice cream sandwiches everywhere, this doughnut sandwich was perfectly balanced - the ice cream beautifully distributed to ensure end-to-end sandwich-eating pleasure. The sandwiches are only made with the honey glazed yeast doughnuts, but honestly, there's nothing better.
As part of our due diligence, however, we did try a few other spots in Chicago.
The motley assortment below comes from two of Chicago's finest: Do-Rite Donuts and The Doughnut Vault.
Do-Rite is adorable with lots of fun flavor options and giant doughnuts.
It's a cake-like type doughnut but with lots more crispy edges to give you a bit of crunch with every bite. Most doughnut places have only one old-fashioned doughnut option, but Do-Rite offers several types - iced, cinnamon sugar, and more. And you know what? Every one of them is amazingly delicious.
The cinnamon sugar (above) is a dynamite combo of spice and sweetness. The inside is surprisingly light and moist.
The chocolate iced actually tastes like rich cocoa, with the same light moistness apparent in the cinnamon sugar old-fashioned.
My other little favorite was the pistachio meyer lemon donut - a lemon iced cake doughnut smothered with pistachio dust.
The cake doughnut was unbelievably tender and moist and addictively spiced.
Do-Rite would be my second favorite doughnuts of Chicago - it's hard to pit old-fashioned/cake against yeast, but Do-Rites are definitely the best I've ever had to date in terms of old-fashioned doughnuts. I still don't understand how they can get the cake so tender and delicate, but I love it, and I miss it!
Doughnut Vault is the hipster child of doughnut shops in Chicago, located in a former bank vault, hence the sweet name.
They offer only a few types of doughnuts, an old-fashioned, a couple yeast flavors, and a gingerbread stack.
The chestnut glazed was a tall beauty of a doughnut, resplendent in height but had an indescribable after-taste that kept me from enjoying it fully.
The yeast doughnut itself was fine but a touch dry.
The gingerbread stack was a trio of doughnuts speckled with spice. Quickly after the first bite into the dry doughnuts did we discover that it was Indian spices, overwhelmingly cardamon, with no hint of gingerbread at all. A sad disappointment.
Later in the afternoon, we swung by ol' Dat's Donuts to finish off Diana and my epic journey to complete Bon Appetit's list of America's Top 10 Doughnut places.
It was going to all finish right here.
A doughnut spot a fair distance from downtown Chicago, tucked away in a dingy little building attached to a BBQ joint.
Oh, how true this is.
Diana and I controlled our appetites (for our imminent dinner in two hours) and ordered just a trio.
The glazed was fine and traditional with the crisp crackle of a good sugar glaze.
The maple iced was rich and an instant ache to the tooth, which Diana ate up gleefully (she's incredible!).
The artificially flavored strawberry was also pretty sweet.
Our next pitstop was not a traditional doughnut shop but a popular brunch place called Nightwood. Brunch + doughnuts are probably one of my most favorite paired words ever (besides crispy duck and, oh, pork belly).
The most popular doughnut, by and large, at Nightwood is the butterscotch bacon, but it was the sunflower streusel of their seasonal doughnut that seduced my eyes.
Served fresh from the fryer, the doughnut was warm, crisp on the outside and heaven on the inside. The blueberry glaze was slightly tart and sweet and the streusel just pure crunchy genius.
The bagel was pretty good (I fear I am slowly becoming one of those New York bagel snobs!) and the trout ultra creamy.
And while the sandwich was plenty good on its own, truth be told, I ordered this dish mainly for the homemade tator tots which turned out to be little golf-ball sized fried chunks of hash browns. So, so crisp and so, so fun!
Diana's brunchy heart is easily wooed by biscuits with sausage gravy, and the sausage gravy here is dark, flavorful and legit with tasty little bites of sagey sausage.
Our final stop was based on fate alone. As we dropped off some items at Diana's friend's house, we discovered she lived atop the Waffles Cafe who recently popped on the foodie radar after they unveiled the mysterious "wonut."
It's available in all sorts of fun flavors and colors. We learned that people are usually limited to a certain number daily, but on this special day, the sky was the limit! Diana and I patiently waited behind two women who proceeded to select 48 different wonuts. Whoa, nuts.
A painstaking ten minutes later, we were carside with two wonuts in hand - sprinkles and a red velvet.
They were okay. It tastes like how a waffle would taste if it was kind of wet (syrupy) and a bit too sweet. Diana liked it though! They are pretty cute.
This was my first fun trip to Chicago, and I found myself super surprised at how delicious all the food was. I'm not sure what I had expected, but I kind of fell in love - who knew such good (and different) doughnuts could be found in one city! Now, if only the winters weren't so brutal...
Han's Nonsensical Rating: Okay, I have to say it, the doughnuts at Firecakes are hottttt stuff !!! (nyuknyuknyukkkk) and Do-Rites can only do right. Man, I got nothing clever to say because really those doughnuts speak for themselves. Must try if you're in Chicago!
68 W Hubbard St
50 W Randolph St
401 1/2 N Franklin St
8251 S Cottage Grove Rd
2119 S Halsted St
1400 S Michigan Ave