I used to do this once a week, but with two young sons and a full-time non-food job, it doesn’t happen as much anymore. Doing this kind of shoe-leather reporting is generally not that big of a deal when covering North Side restaurants, as so many of those spots are covered ad nauseam and sometimes even reviewed on Yelp even before they opened.
The South Side, however, is different. Restaurants can be open for a year sometimes before they’re discovered. Driving around the South Side looking for chow, I find, still yields discoveries and delightful surprises. Having a rare free day, I recently hopped in my Porsche (OK, truthfully, my trusty Ford Flex dad-friendly SUV) with a laptop, a box of baby wipes and bottles of Gatorade in tow and just drove for six hours. I found spots I’d somehow missed in the past that have been around forever—like Haire’s, which definitively serves Chicago’s best fried shrimp—and newer places like Nita’s, which brews one of Chicago’s best gumbos.
I augmented the discoveries of this recent trip with the places I’ve found on past drives to bring you what I hope is one of the more comprehensive eating guides to Chicago’s South Side.
Note: I’ve deliberately not covered Little Italy, Pilsen and Chinatown spots here, which though technically on the South Side, could be eating guides on their own. I have of course probably missed your favorite secret spot. If I have, please share. We are always looking for the good food here at RedEye.
Old Fashioned Donuts
11248 S. Michigan Ave. 773-995-7420
Like Bigfoot or the Loch Ness monster, the apple fritter ($4) from Old Fashioned is legendary. Unlike those two, it actually exists. The size of at least four regular apple fritters with a fried mahogany-and-marble sugar glazed crust, this is the singular item that made me become a food writer. I couldn’t believe something so iconoclastic and delicious existed for maybe decades and I never knew about it. Once I discovered it, I reasoned there must be hundreds of buried edible treasures all over Chicagoland to discover. Since then, I have not stopped looking for them.
1235 W 95th St. 773-366-3110
Like Old Fashioned, Poppin has a huge apple fritter. It’s decent, but what you really want is the basic glazed ($1), which features an airy layered interior that reminds you of a sweet croissant. Which is to say, it’s basically a cronut, but no one here would ever say that. What they will say as they hand over your bag of fried dough goodies is “Have a poptastic day!”
8251 S. Cottage Grove 773-723-1002
You want the giant Texas-sized chocolate glazed ($3.35). Or if you’re not into desserts the size of life preservers, check the blueberry cake doughnuts ($1.05), featuring a buttery crumb flecked with juicy berries.
2907 S. Archer Ave. 773-523-1121
On paczki day, the lines outside this Bridgeport stalwart look like queues outside an Ed Sheeran concert. Most other times of the year, you can just pop in for maple bacon donuts and fluted crullers. You want the savory bacon bun ($1)—a yeasty roll stuffed with bacon and pork—so you might want to come early as they often sell out.
8125 S. Halsted St. 773-483-8111
Featuring an oil slick dark roux (a cooked mix of fat and flour that thickens gumbo), fat pink shrimp, slivers of spicy caramelized chicken sausage, sweet pepper and cayenne, this bowl is a heartwarmer ($10.99/small, $16.99/large). The smothered catfish, scratch biscuits and sweet potato pancakes ($10.25) are also pretty fine.
8100 S. Stony Island Ave. 773-734-2788
Until recently, Three Chef’s was the best gumbo bowl I’d had in Chicago, but there’s a case that Nita’s bowl, which is stuffed with silky crab and scallops, thick shrimp, and zesty chicken andouille sausage curls is even better. The gumbo ($10/16 oz. half order) is a recipe passed down from Irving Sheldon Jones to his daughter, the restaurant’s namesake, Anita. For 25 years, Anita cooked a huge annual New Year’s Louisiana-focused feast that her family refers to as “the chase,” where her gumbo was prominent. No longer confined to Anita’s family, now all Chicago citizens can taste the chase!
Haire’s Gulf Shrimp
7448 S. Vincennes Ave. 773-783-1818
This fried shrimp is the bomb, literally, which is to say it comes in two sizes: “the small bomb” ($11.66) or “large bomb” ($15.88) bag. The small bomb is akin to most local shrimp shacks half-pound portions. Unlike most shrimp shacks, the shrimp is butterflied, flaky-crusted, dusted with a sprinkle of salt and flecked with surprising treasures of black pepper. Fatso’s Last Stand has been my standard bearer for Chicago fried shrimp, but after dusting off a small bomb here, I’m convinced this is Chicago’s greatest crispy crustacean. Also, Chance the Rapper has been here at least once, as evidenced by the photo of him and the Haire’s crew that hangs below the counter.
3259 E. 95th St. 773-933-9855
Today it’s pretty common to compare addictive food to rock cocaine, but back before casual drug references in food writing were de rigueur, the smoked shrimp ($22.99/lb) served here were one of the first foods I ever saw referenced as “crack.” Years later, the shrimp and the peppery smoked salmon ($16.69/lb) are still as enticing as any street drug in existence or yet to be invented.
CHICKEN AND OTHER FRIED GOODIES
6659 W. Archer Ave. 773-586-2115
These are not heavy flour-dusted franchise fare. Rather, the golden crisp-skinned poultry ($8.70/4-pc. dinner) shatters to the bite and is more reminiscent of the supper club or homestyle Sunday dinner fried chicken. Once you stop in, you will make it a mission to return before every flight out of Midway.
Hienie’s Shrimp House
10359 S. Torrence Ave. 773-734-8400
The crinkle-cut fries are garden variety frozen Simplot. The shrimp ($10.30) is decent, but no match for the tender butterfly-cut stuff served at Haire’s. The chicken ($5.40/2 pc. dark) is only about 75 percent as good as the Mini Hut chicken. However, neither of those spots serves their wares with Hienie’s neon-orange mustard-spiked tangy hot sauce that is revered so deeply by locals that they walk out with bottles of the stuff.
Chicago Wingz Around the World
700 E. 47th St. 872-818-5260
Any corner shack does Buffalo flavor. But, how many chicken wing spots sling 30-plus sauces, including gems like honey lemon pepper, Parmesan garlic, sweet ginger barbecue and bangin’ ranch ($6.49/6 piece)?
Chicago’s Home of Chicken and Waffles
3947 S. King Dr. 773-536-3300
The chicken is crispy and the thick waffles ($10-$20) waft a haunting yeasty perfume, but it’s the chicken livers ($13-$14), pudding-like rich in the middle and enrobed in a crust that flakes like fine mica, that keep me coming back.
5055 S. Prairie Ave. 773-548-5375
Most jerk chicken in Chicago is some kind of arms race to burn the first layer off your tongue with a bucket of scotch bonnet peppers. Bronzeville’s juicy-to-the-bone bird ($7.50/lunch portion) has a slow burn which allows you to appreciate the balance of pepper, allspice and salt that also coats the crisp blackened skin.
LAMB AND GOAT
4852 S. Pulaski Road 773-523-3700
Every culture has a restorative broth, the kind of bowl that fuels you for a day of work or brings you back from the infirmities of a terrible cold. Americans have chicken noodle soup. The Vietnamese have pho. And the Mexicans have birria. Birria is a funky deeply-rich goat bone broth stuffed with tender shredded meat spiked with fiery arbol chilis, a shower of cilantro and a tangy spritz of lime. The bowls served here ($12.25/small bowl) will make your nose run and your heart beat quicker.
3139 S. Halsted St. 312-326-6898
You’d think a place named after one of the most famous pieces of dim sum would make killer dumplings. And they are decent, but the dish here that’ll blow your mind is the awkwardly named “cumin flavor lamb with bone.” The lamb ($16.95) melts in your mouth but leaves behind a grassy fragrant cumin perfume that makes you feel like you chased the meat with a world class shot of chili.
605 W. 31st St. 312-949-1314
There may be no such thing as a free lunch, but there is such a thing as a cheap (usually the domain of fussy cheffy $100-and-up meals) prix-fixe meal. Don’t let the price full you; chef Guan Chen is a top toque with a talent for melding odd ingredient combos like strawberry, beef and lemongrass to upscale Chinese dishes way before Stephanie Izard, Won Fun or Imperial Lamian ever did. Here, $35 gets you four courses. You’re not locked in to the chef’s whim either, as most courses offer a plethora of options like rack of lamb with bonito plum sauce or crispy quail with fresh lemon.
PIE AND ICE CREAM
1844 W. 95th St. 773-779-9105
You probably remember that scene from Forrest Gump where Bubba talks about all the ways to cook shrimp. It’s kinda like that at Jimmy Jam’s, but instead of shrimp, you get to explore all the ways to use a sweet potato. There’s sweet potato pie, cupcakes, bread, sundaes, sandwiches and baked potatoes stuffed with cheese, peppers and chicken ($2.75-$8.75).
9233 S. Western Ave. 773-238-7075
Joseph Sapp opened the Original Rainbow Cone in 1926 near the corner of 92nd Place and Western Avenue, serving five flat slices—not scoops—of chocolate, strawberry, Palmer House (vanilla studded with walnuts and cherries) and pistachio ice cream and orange cream sherbet combined into a rainbow of layers packed atop a wafer-style ice cream cone ($4.29/small cone). Today, his granddaughter Lynn runs the place, which is now as iconic as places like Gibsons, Al’s Beef or Mario’s Italian Lemonade.
10337 S. Kedzie Ave. 773-239-1243
The wafer-thin green peppers in the giardiniera create a snappy spicy contrast to the juicy paper-thin rolls of beef sandwiched between the gravy-soaked bun ($5.09). If the fries here remind of you a certain potato product served by a fast food joint known for their golden arches, you’re not hallucinating. Pop’s fries are factory seconds that McD’s rejects for minor visual imperfections.
311 E. 75th St. 773-994-2428
If you’re really trying to understand the origins of Chicago-style barbecue—that particular brand of smoked meat featuring rib tips ($12.25) soaked in sauce and topped with white bread—Lem’s is ground zero.
Honey 1 BBQ
746 E. 43rd St. 773-285-9455
Robert Adam’s Sr. is the modern generation of Chicago-style smoke-masters. He works his smoker like Jimi Hendrix picked a Fender Stratocaster, turning out firm juicy ribs ($12.99/half slab) with a thick cracklin’ bark and juicy hot links ($3.99).
2518 W. 63rd St. 773-776-7440
Let’s say it’s one of those Chicago winters when cars get frozen on Lake Shore Drive and you’re suffering from major seasonal affective disorder (SAD) and you don’t know how to escape the doldrums. One surefire way is to hop over to this bastion of Caribbean cuisine for a taste of the islands or, in the case of the juicy Belizean chicken, a taste of Central America. Don’t miss the panades ($5.95), which are basically fried empanada-like dumplings that come with fizzy pickled cabbage that offsets their carb-tastic richness.
954-960 W 31st St. 773-823-7336
Feast on Kopo Wangs ($8), which are smoked, roasted and deep-fried, producing a chicharron-like crispy skin. The interior flesh oozes with “AP” sauce with sweet and fizzy gochujang, a red chili paste. Also, don’t miss the Ko-Po beef ($13), a Philly cheesesteak run through the Korean larder, featuring marinated grilled bulgogi, golden caramelized onions, grassy ribbons of shishito pepper and gochujang red chili butter.
1462 E. 53rd St. 773-288-1010
With his Logan Square spots Billy Sunday and Yusho, Matthias Merges has proven himself a solid curator of cool. At A10, he’s a bit more classic, with his crew turning out nonna-worthy pastas and airy focaccia. Though his wares here aren’t as hipster-baity as they are up north, they’re so impeccable, you’ll still fall hard for toothsome bucatini carbonara ($19) dripping with egg and cured pig jowl, aka guanciale.
3267 S. Halsted St. 312-929-2486
Nana is the epitome of great brunch, which is to say it offers excellent super-savory hangover helpers like huevos rancheros ($13), but also dessert-worthy breakfast like strawberry rhubarb French toast dripping in vanilla cream ($13). Dinner and lunch—which skew local, sustainable and organic—are also pretty top notch.
BLUE COLLAR GOURMET
2701 S. Eleanor St. 312-724-8811
Not only does he have maybe the greatest head of hair amongst Chicago chefs, chef/partner Kevin Hickey has a way with duck. His rotisserie duck ($65) is lip smacking complemented by crispy duck fat roasted potatoes and a lightening assortment of baby kale, citrus and radishes. If you still need calories after consuming this baby, I suggest the fried cheese curds ($8), served with bloody mary ketchup and hop-infused mayo.
COLLEGE HANG AND CAFE
1100 55th St. 773-256-0702
Medici on 57th has been the de facto lunch spot for UChicago kids and professors for generations. It’s still pretty good, and I find myself craving their garbage salad a few times a year, but these days, all the UC faithful are now heading over to this spot for blackened catfish, puerco pibil tacos and old school reubens. It’s kind of like an eclectic dorm cafeteria headed by good cook (menu and prices subject to change).
3901 S. Michigan Ave. 877-275-5852
Before all the cool restaurant groups started pimping “meat and three” cafeteria-style restaurants serving soul food classics, there was Pearl’s, where you will gorge yourself on fried tomatoes ($6), creamy grits and shrimp ($9), and short ribs ($24) smothered in gravy, peppers and onions.
10426 S. Western Ave. 773-779-2739
Score World Beer Cup medal-winning brews and juicy grass-fed burgers ($10.99).
Michael Nagrant is a RedEye special contributor.
This article first appeared in Redeye Chicago in a different form.