24/7: The best of the South Side’s all-night dining destinations

Kevin\'s Hamburger Heaven, photo by Ellis Calvin

There are any number of guides to Chicago’s culinary wonders. From the North Side’s Alinea to the North Side’s Charlie Trotter’s, Chicago is littered with four-star wonderlands. But these gourmet eateries share one weakness: they all close. And once they do, the South Side may have the upper hand. Some of the city’s tastiest–and greasiest–food can be found at its 24-hour cult spots, where night owls and frazzled waitstaffs burn the midnight oil in sleepless solidarity. To help wake you up to the nocturnal bounty around you, the Weekly presents our guide to food after dark on the South Side.

Dox Grill
600 W. Pershing Rd.
A strip of little but empty lots and warehouses, Pershing Avenue at the southern end of Bridgeport is home to three old, dark, and dingy 24-hour grills. Driving past at night, one might be understandably shocked to see open businesses and, were they raised on suburban Olive Gardens and Buffalo Wild Wings, further shocked that anyone might actually patronize them. Dox Grill, the westernmost of the grills, claims to specialize in “homestyle breakfast anytime.” Homestyle is right–Dox is barely better equipped than your own kitchen. A tiny room whose furnishings and off-white surfaces suggest the 1970s or earlier, it contains little more than a dozen stools around a counter, two employees, a soda fountain, a coffee maker, and a deep fryer and a griddle where the magic happens. The menu, written on the wall behind the counter in a wide variety of media in various states of legibility, is made up exclusively of the kind of greasy, triple-fried fare that hurts so good on the way down and takes years off of your life. My Polish sausage was gigantic, deep fried, and delicious. The coffee is no-bullshit, hard-as-nails. It’s a real Chicago kind of place. Avoid the bathroom if you can, unless you are going in there for a heroin overdose. (Dave McQuown)

New Archview
3480 S. Archer Ave.
The queen mother of diners, New Archview should be your home. Boasting three large parking lots, New Archview is hopping at all hours of the night with a colorful cross section of humanity. Whites, blacks, Asians, yuppies, truckers, potheads, and lots and lots of cops put aside their differences to partake in diner food of the finest quality. New Archview’s Greek-style menu is the size of a small magazine and covers a wide range of foods, from stir fry to pot roast–anything so long as there’s meat in it. Food and booze are both fairly inexpensive, though the menu does contain a few more upscale items like roast lamb for the sophisticates. Whatever you get, it is going to be way, way too much food. The veal cutlet gravy sandwich is highly recommended. Come during the holiday season to see some seriously wicked window decorations. (Dave McQuown)

Kevin\'s Hamburger Heaven, photo by Ellis Calvin

Kevin’s Hamburger Heaven
554 W. Pershing Rd.
“NO OUTSIDE FOOD, WATER, ALCOHOL, RED BULL, ETC.”: these words in somber Sharpie I beheld, Scotch taped to the entrance of Kevin’s Hamburger Heaven. From the barstool, my bloodshot eyes weave between the virtuoso at the griddle and the menu’s many riddles: typos more remarkable for their systematicity than their excess–”special Seasoning” in the singular must always be capitalized s/S, while “Special seasonings” must invert the fraction; peremptory disclaimers that introduce objections only to dismiss them–”Tenderness NOT guaranteed on ‘Medium Well or Well Done’ Steaks Positively NO Refunds”; fare so American that I’ve never seen it before. The griddle is an apparatus of capture. It exercises a pornographic fascination, laying bare exotic tools and movements I’d never dreamt of. A lure, a sinister dance; under its spell I forget my appetite. The sudden arrival of my vanilla malt ($3.99) breaks my trance. Not malty enough but substantial; I double-fist the two Styrofoam cups. The patty melt ($3.99) and “The One and Only” ($3.69) are recommended; these patties are not the kind that queue up in plastic bags, kept at polite distance by wax-paper, marching forth frozen and Spartan. No, these came to be through the griddler’s wizardry. Although, intensively and extensively, the pickles overwhelm, the grilled onions are hot and sweet. Upon payment, the waitress counts my change twice, muttering, “What the fuck am I doing?”, and promptly undercharges me $1. Kevin’s no longer offers karaoke. (Austin Gross)

Harold Washington\'s reassuring gaze at Izola\'s, photo by Ellis Calvin

Izola’s
522 E. 79th St.
Legend has it that, back in the early ’80s, Harold Washington made his decision to run for mayor right here in Izola’s. Today a friendly portrait of the late and much beloved politician beams down from the wall of the dining room, which bustles with laughter and conversation late into the night. The soul food restaurant, open 24 hours every day but Wednesday, feels comfortable with a touch of faded class. The walls are lined with numerous other photos in addition to Washington’s, as well as paintings, plants, trophies, and a jukebox. The menu has a few unusual items, like a “Head lettuce” ($2) and a surprisingly good Denver sandwich ($4), which proved to be an omelet hidden in bread. The real treat, though, is the crisp, juicy fried chicken, accompanied by toasted white bread and exquisite French fries. It’s not exactly a typical late-night joint–be prepared to wait for your food for upwards of fifteen minutes–but for a sit-down good time, head to 79th Street. Cash only. (Sam Feldman)

Huck Finn Donuts & Snack Shop
3414 S. Archer Ave.
The website for the three Huck Finn locations announces that “the Huck Finn operation consists of three basic groups of products: Food, Donuts and Ice Cream.” Finally, a nutritional pyramid America can get behind. I can’t speak for the Food or Ice Cream groups, but Huck Finn’s donuts are really something. If donuts big enough to swallow your arm ($2 each) sound intimidating, never fear; normal-sized fried toroids ($1) are also available, as well as muffins and other pastries. The fried glazed crullers are particularly good, but everything’s a number of steps up from Dunkin’ Donuts’ stale fare. The atmosphere is also a lot more welcoming, not to mention amusing. “Restaurant,” declares the awning out front. “Donuts.” Just inside the door, a vending machine promises “Huge sticky stuff.” “Other items included,” it clarifies. Another vending machine offers alien projector rings (as well as the elusive “other items”). Festive pumpkin paper cutouts complete the mood inside, while a “Carry Outs” sign spins slowly in the wind out front. (Sam Feldman)

Huck Finn Donuts, photo by Ellis Calvin

Express Grill/Jim’s Original Hot Dogs
1250 and 1260 S. Union Ave.
Luxurious they’re not, but the two hot dog stands in the shadow of the Dan Ryan Expressway are pieces of history. In 1939, Jimmy Stefanovic combined an all-beef sausage with mountains of grilled onions, mustard, and peppers, put it on a bun, and served it with fries. Thus was created the original Maxwell Street Polish, a tradition that has been passed down in the family. Jim’s Original Hot Dogs is still owned by Stefanovices, while next door the Express Grill is owned by descendants of Tom Lazarevski, Jimmy’s cousin, who quit Jim’s to try and make it on his own. At all hours of the day and night, those in the know can be seen exiting the highway at Roosevelt Road and circling back for a steaming hot no-frills Polish. Be warned, though: “no-frills” means no chairs, no tables, and no inside, just a slim counter on the outside wall to rest your sausage on between gulps. (Sam Feldman)

Maxwell Street Depot
411 W. 31st St.
No piece on 24-hour joints could omit Depot. The legendary Polish place where even the fries come with fries is never empty. Whether it be tipsy Illinois Institute of Technology students, Bridgeport artists, or just sausage connoisseurs from anywhere within driving distance, there’s always someone waiting in line for simple but filling fare at highly reasonable prices. The pork chop sandwich, a specialty, often comes with bones inside; careful not to choke on the authenticity. (Sam Feldman)

Photos by Ellis Calvin

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