The Big Dat at Dat Donut
Before there were out-the-door queues for white chocolate brownie doughnuts at Doughnut Vault and espresso-cream brioche doughnuts at Do-Rite, there was Dat Donut. Since 1994, owners Darryl and Andrea Townson have been baking deep on the South Side in Chatham. Dat's confections whirl out on a lazy Susan from behind bulletproof glass. You point to what you want, and whoever’s at the window loads it onto the tray and spins it around. The device is hardly big enough to contain the shop's pièce de résistance—the Big Dat, a pumped-up glazed doughnut that’s a full seven inches in diameter. Even behind thick glass, under fluorescent light, its icing glimmers and dazzles. Bite into one and your mouth gets hit with the perfect amount of sweet before the glaze gives way to the fresh, spongy dough, which is remarkably light—less greasy than yeasty. Dat's thick, tangy, and doughy custard doughnut ranks a close second, with its eggy filling and powdered-sugar exterior. Then there are the chocolate long johns, apple fritters, Boston creams—the shelves hold at least 25 more types, too. Dat makes them 24 hours a day, six days a week, taking a break only on Sunday nights (and since the staff replenishes the racks frequently, you’re bound to get a fresh doughnut every time). The shop itself is small, though you can linger and watch the bakers kneading, hand-cutting, and frying the dough behind the big glass window in back. The Townsons do a powerful thing here: They make kick-ass doughnuts, while also providing jobs and a little extra sweetness to a community that truly appreciates their presence.
A Sundae at Margie's Candies
It's easy to imagine this frozen-in-time ice cream parlor scooping up something sweet for Al Capone and the Beatles (which it has). The red-neon-lit shop has been around since 1921, and it looks the part. Kitschy knickknacks clutter the shelves, and mini jukeboxes charm on the tables. Sweet tooths of all ages scooch into the tight vinyl booths, panting for one thing: Margie's sundaes. They arrive on a silver platter, in a white clamshell bowl, alongside a silver gravy boat of hot fudge. The latter is key. You see, Margie's also makes chocolate, so the shop’s not messing around when it comes to its rich, thick fudge. At Margie’s, they make their own 18% butterfat ice cream, too. Regular sundaes are two or three mighty scoops, plus whipped cream, nuts, and a cherry. Add the hot-fudge gravy boat and you're pretty much guaranteed to fail at eating the whole thing. Not that you shouldn't try. Margie herself ran the shop until she passed away in 1995. But her spirit, and her bloodline, remain. Relatives of Margie still run the timeless parlor. And here’s hoping they always will.
A Tex-Mex Plate at Dove's Luncheonette
Walking into Dove's Luncheonette, in Wicker Park, I grab a stool at the stainless steel counter, and a waitress with jangly hoop earrings and bright red lipstick plunks down a steaming mug of coffee before I can even get my coat off. Soul music drifts from the jukebox, and rows of tequila bottles rattle behind the bar. The wood-paneled diner time-warps me back a half century to a dusty Rio Grande town, a place where drifters might stop in for a quick sandwich and shot under the lazily spinning ceiling fans. It's like being in a Nelson Algren novel—which is smack where Dove's draws its inspiration from: It’s named after A Walk on the Wild Side hustler Dove Linkhorn and modeled after the joints of his era.
Here, though, the customers aren't down-and-out types, but rather tattooed and beanie-clad neighborhood folks. And Chef Paul Kahan's Tex-Mex menu isn't typical diner fare, but a hot-spiced step up. Don’t miss the tamal de cochinillo, a pork-stuffed sweet corn tamale topped with andouille gumbo, giant Gulf shrimp, and spears of crunchy fried okra (it’s served up sizzling in a cast iron skillet). Chicken-fried chicken can be had all day long, doused with spicy chorizo gravy and sweet peas. Alas, you’ll need to be an early riser to experience the pancakes topped with ambrosial hibiscus-poached apples. Not so with Dove’s 70 tequilas and mezcals—they flow any time of day. As with any proper diner, most meals here are punctuated with pie, maybe cinnamon-tinged horchata cream or tart lemon meringue. Put your order in before you finish your main course, though. Those pies can disappear from the menu board lickety-split.
A Stuffed Pizza at Giordano's on Rush Street
You've heard of Chicago deep-dish pizza: loved by some, mocked by others. (Yes, I’m talking to you, Jon "tomato soup in a bread bowl" Stewart.) What you might not know is that there's something deeper than deep-dish—a bigger, doughier version known as stuffed pizza. It stacks up like this: a layer of dough, followed by mozzarella cheese, another layer of dough, then sauce and toppings. Did you catch that? Cheese is packed between two crusts, not laid on top of one, as with traditional deep-dish.
Giordano's bakes the mightiest version, an insanely hulking pie whose slices weigh more than a half pound each and whose crust rises two inches off the plate to cradle the mound of tangy sauce. It’s comfort food supreme—soft, warm, and so, so filling. These pizzas thud onto tables around the city (Giordano's has 50 or so restaurants in the metro area, plus a few beyond Illinois). But my favorite location is downtown, on Rush Street—the one where all the tourists go. I love to look around the clamorous room and watch everything, from families with fidgety toddlers to spiky-haired Japanese couples to Urdu-speaking university students: everyone trying to decide whether to eat their enormous, gooey slice with a fork or by hand. A nifty bonus is the view into the open kitchen, where large-forearmed workers stretch and toss dough to each other, then pile the ingredients into vast iron pans and heft them into the oven. One glance, and it's clear why it takes 45 minutes to cook each double-crusted whopper.
The CB&J Sandwich at Hopleaf
Hopleaf has been pouring suds in the groovy Far North neighborhood of Andersonville since 1992. It was one of the city's first beer bars, and it's still among the best. Beer-a-philes get slack-jawed eyeballing the 60 taps and 200-deep bottle list, and are giddy carrying burbling goblets back to their seats. The cozy room has a European-café vibe, with close-set tables, the low din of conversation, jazz records playing, and glasses clinking as bartenders wash them as fast as patrons can polish off their pints. While this might all sound like pure perfection, it’s the Belgian-style food served here that takes Hopleaf to the next level. Ale-soaked mussels and thin-cut frites are the house specialty, but my money goes to the CB&J sandwich. That's house-made cashew butter, fig jam, and raclette cheese, amassed on sourdough bread and pan-fried until crisp and oozing. You couldn't ask for a better beer absorber. The side of black-peppery Stilton mac and cheese is just a happy bonus. It'll take a while to clear the crumbs off your face and wipe the grease from your fingers, but once finished, you're good for another beer or three.
A Martini at the Green Mill
Want to get a glimpse of where Al Capone once hid his bootlegged booze? The Green Mill was Capone's favorite hangout back in the day, when he’d swirl a cocktail and listen to live jazz. His pal, Machine Gun McGurn, part-owned the club, which was central to their bootlegging operation. If it’s not too busy, ask the bartender to show you the trapdoor behind the bar that leads down to tunnels where they hid the hooch. The art deco décor hasn't changed much since the 1920s. Velvet-cushioned booths curve under paintings in florid scrolled frames. Green candles flicker on white-clothed tables, while scalloped ceiling lights add a low yellow glow. A couple of seasoned bartenders patrol the glossy wood bar that swoops halfway through the room. They'll shake up a Sidecar or Manhattan or pop open a Pabst for you. But they're best known for their Martini: a crystal-clear, up-with-two-olives, non-fancy-pants gin bracer.
Order that Martini in the afternoon and it'll be you and a handful of grizzled regulars minding their own business in the dim light. At night, the crowd sharpens, and you'll be drinking alongside serious jazz-heads who will shush you for talking during the sets. Imbibe on a Sunday and poets will be your companions. The Green Mill is the birthplace of the poetry slam, still held each Sunday evening, which explains why much of the bathroom graffiti is written in verse.
As for sitting where Capone sat, you really can do that, too. His booth is the one at the end of the bar, on the north side—the only seat in the house that has a view of both doors.
A Jibarito at Cafe Central
Chicago has given the world many great creations: brownies, the zipper, skyscrapers, deep-dish pizza. Yet people forget about the jibarito. Local restaurant owner Juan "Pete" Figueroa invented the sandwich in the mid-1990s. His big idea? Take two flattened, crisp-fried plantains and use them as "bread" for a Puerto Rican steak, cheese, and garlic-mayo sandwich. The concept spread fast, and soon chicken jibaritos, shrimp jibaritos, curry-mayo jibaritos, and more riffs on the original emerged from neighborhood kitchens.
I like to stay traditional with my jibarito, and Cafe Central makes a steak version that's as classic as it gets. It's a mom-and-pop spot, in business since 1952, where teapot-print drapes hang in the window and mosaics made of multicolored beans adorn the walls. Older Puerto Rican couples slurp pigeon-pea soup in the front booths, while extended families gab over platters of rotisserie chicken and yellow rice at the tables in back.
Regarding the jibarito: It arrives by its lonesome on a white plate. There are jibaritos in this world piled so high your jaw unhinges to take a bite, and jibaritos so greasy a river runs down your hand, and jibaritos so garlicky you can't speak to anyone for three days after eating. Cafe Central's sandwich is none of those things. Compact and subtle in sauces, it's easy to devour. Each bite crunches through the plantain and into melted American cheese, two thin slices of steak, and cool tomato and lettuce. The meat is tender and juicy, the ingredients balanced so they don’t slop all over the place. Other cities have discovered the allure, but the jibarito remains best munched here, in a humble hometown restaurante.
Breakfast at Lou Mitchell's
The waitresses at Lou Mitchell's are for real. They're worldly and wise and wear sensible, thick-soled shoes. They have names like Kathy and Dot and Virginia that are sewn in big letters on their aprons. It's hard to tell their age, but they're not young. Dot once told me she was 80. They're strong as Hercules, lining heavy plates up their arms and then dealing them on the table like cards: fluffy, feta-packed omelettes; thick-cut Greek toast (made with a dense, rustic sourdough Greek bread); fruit cups; and stacks of airy silver dollar pancakes. They know their regulars ("Hi, Charles. How are the kids?") and call everyone "sweetie."
Lou's is an old-school Greek diner. It opened in 1923 and, three years later, found itself near the start of a new road called Route 66. Hungry travelers fueled up at the counter and in the little booths before setting off on their journeys. Today, locals and tourists still crowd in for the Main Street vibe and jumbo breakfast dishes. People chat, newspapers rustle, silverware clatters—close your eyes and you could be in Winslow, Catoosa, or some other small town instead of downtown Chicago.
Goodness prevails here. If there's a line to get in, the hostess hands out free doughnut holes sprinkled with powdered sugar to ease the wait. Then come the mini boxes of Milk Duds. Once you're at the table, further freebies arrive: dishes of stewed prunes (tastier than they sound) and soft-serve ice cream. By the time I leave—after Audrey calls out, "Enjoy your day, dear!"—all is right in the world again.
A Brew at Di's Den
Di's is my neighborhood bar, a few blocks from where I live on Chicago's Northwest side. It's not famous or glamorous or a dive turned hip hot spot. It doesn't even have beer on tap. What it does have is true local character.
There really is a Di. She's a sprightly septuagenarian who's often around, sometimes tending bar, sometimes just chatting with customers. Regulars fill the stools, longtime Chicagoans who work as garbage collectors, nurses, and construction workers. These folks take a pull on their Buds and give you an earful about the mayor, taxes, and potholes. They also throw darts. Di's entire back room is devoted to the pursuit.
That all goes by the wayside, though, if there's a big game on TV. The Blackhawks have a rapt audience, the Bears a grousing one, but the Cubs are the end-all and be-all. Di is a rabid fan, and she has been waiting a long damn time for a World Series win. She makes sloppy joes or buys pizza or has other free food during critical games. Wins might mean a round of apple pie shots on the house.
Flashy cocktails and slick décor? Not at Di's. An authentic patch of Chicago? Bull's-eye.
A Pastoral Picnic to Go
It's a summertime ritual to picnic in Millennium Park during the free concerts that happen most evenings. Some folks sit on the grass and bust open a bag of Doritos. Others bring lawn chairs, small tables, and full-on Bordeaux, Brie, and saucisson feasts. For people who fall between these extremes, there are Pastoral's sandwiches. The wee deli heaps quality fixings onto crusty baguettes three blocks from the park. Which means, as the sun drops and music rises from Frank Gehry's swooping silver bandshell, you're ready and chomping on the Blue Pig N' Fig (serrano ham, blue cheese, fig preserves), Sinfully Healthy (roasted turkey, mango chutney), or San Daniele (prosciutto, mozzarella, pesto). The creative flavor mashups and ingredients from distinctive small-batch producers set these sandwiches way above the norm. Pastoral sells bottles of wine and beer to boot. Call in your order a few hours in advance to avoid a lengthy wait.