It is a truth universally acknowledged — or at least acknowledged by this correspondent and fan of sweetened baked goods — that Chicago’s best doughnuts are south of 55th Street. A few Saturdays ago, I decided to prove that to a friend who was visiting from Wisconsin for the weekend. In his Toyota Prius — the most North Side car imaginable — we went in search of the best doughnut on the South Side.
Our first stop was Dat Donut, in Chatham, which shares a storefront with Uncle John’s, one of Chicago’s best BBQ joints. Dat’s motto is “Too Good to Dunk,” which I took as a dig at Dunkin’.
“We’re looking for the best doughnuts on the South Side,” I declared to the young lady behind the counter.
“That’s the whole case,” she said.
“What’s your specialty?”
“Pound cake. We got buttermilk and lemon. Lemon is the freshest.”
“What makes you the best?”
“We’re different from Dunkin’ and Old Fashioned. Dunkin’, they have their doughnuts shipped in. Ours are softer than Old Fashioned.”
“Better than Old Fashioned?”
She waved dismissively.
My friend and I ordered the lemon. We split the doughnut in half. We were going to be eating a lot of doughnuts that day, so we had to pace ourselves.
“It takes like cake!” my friend said, approvingly.
Next, we visited Poppin’ Dough, in Washington Park.
“You came to the right place,” said the man behind the bulletproof glass when I said we were looking for the South Side’s best doughnut. “We were on Chicago’s Best. I forget what network it was on, but it was Bernie Payton.”
Poppin’ Dough’s specialty is a maple bacon doughnut, but no one had baked one that morning, so we ordered a simple glazed. My friend thought it was “a little soft.” There must be better doughnuts on the South Side, we both thought.
There is, at Old Fashioned Donuts in Roseland. I’ve visited Old Fashioned a dozen times, but never have I ordered an apple fritter. At 810 calories, I can’t eat one by myself. (Note to doughnut shops: Don’t advertise the calories in your wares. It discourages customers.) Now, though, I had someone to share it with.
“I heard this is the best doughnut shop on the South Side,” I told the girl behind the counter.
“It’s possibly one of ’em,” she said.
Old Fashioned has been in business 52 years. Old Fashioned doesn’t need to boast. Longevity is proof of quality. Everything about Old Fashioned is old fashioned, from the wooden doors to the menu board with plastic letters embedded in grooves. The ‘L’ in ‘WHOLE’ is an upside-down 7.
The fritter in the bag felt like it weighed two pounds.
“It’s got a heft to it,” my friend said.
I pried apart the fritter, marveling at the freshness of its doughy flesh. I bit through the hard glazing and sank my teeth through the softness inside. I picked at the crust, then at the cubes of baked apple embedded therein.
“It’s got a lot of cinnamon,” my comrade observed.
“It’s got a lot of everything going on,” I said. “This is the best one so far.”
Donut Dudes, in Beverly, was opened in December 2022 by three brothers. Its menu board is a video screen displaying the specialty doughnuts of the day: Kit Kat Krumble, Oreo Krumble, Cosmic Brownie Batter, PB&J Filled. By 2 in the afternoon, there was nothing left in the display case but Strawberry Krumble and Fruity Pebbles.
“We were almost empty by 11,” said the girl behind the counter. “A lot of people ask if we have apple fritters, munchkins. We have filled. We have strawberry cheesecake.”
We ordered the Strawberry Krumble, which was $2.79, the most we’d paid for a ring doughnut. We didn’t finish it. The doughnut was cloyingly sweet.
“I think they’re trying too hard,” I told my friend. He agreed.
“Meh,” he said. “I think your analysis of them trying too hard is accurate. It isn’t for me. The ambience of Old Fashioned was great. It seemed like a real place.”
On Kedzie Avenue, in Ashburn, we passed D&D’s Place, a doughnut hut topped with a cutout of a baker lifting a chocolate frosted. A handwritten sign in the window announced, “Do To Our Daughter’s Wedding We Will Be Closed Sat. Thanks For Your Love Peace & Joy.”
“That’s too bad,” I said. “This looks like a good place. We could have made it six.”
My co-pilot seemed relieved that D&D’s was closed.
“I don’t think I could have made it. I’m stuffed.”
Our final stop was Pticek & Son Bakery, a Polish bakery in Garfield Ridge. We walked in at 3, just as the women in white smocks were about to lock the door. There were five doughnuts left, all chocolate frosted. It was a doughnut with presence and gravitas, solid but soft, sweet but not sickeningly so.
“As for a classic chocolate cake doughnut, it sets the bar pretty high,” my friend said.
A man in a pickup truck parked at the curb bellowed Pticek’s praises.
“It’s real good shit if you’ve never had it before! They make the cheesecake with sour cream.”
“This may be the best one yet,” I said.
We had a winner. Or two winners. Pticek’s had the best classic doughnut, Old Fashioned the best fritter. If we missed a good South Side doughnut, let us know.