A few years ago, the area within walking distance of the Red Line's 69th street station was a mass of storefronts: beauty salons, barber shops, urban boutiques. Now, head east past King Drive, from 69th to 75th, and it's impossible to miss the change in the air. Innovative eateries are popping up, florists are moving in and decorating the neighborhood...it seems these folks aren't waiting to be told what the "hot" new area is: they're creating it themselves. Old standbys do remain, a good thing, as they give the neighborhood character, preventing an unwelcome homogenous spirit from settling in. In its place is an eclectic, fashionable mix of downtown and uptown, with plenty of room to grow.
Good for groups
Daddy O's Jerk Pit
This Chatham-based chicken shack has been cooking up some of the best Caribbean-style food on the South Side for over twelve years. Although the majority of its business is take-out, this ramshackle storefront does have some seating for folks who've come out of the way in order to sample Daddy O's wares. It's a comfortable atmosphere, with reggae, ska and other lilting Caribbean music styles playing in the background.
The standout meal at Daddy O's is jerk chicken, and it's prepared with lots of effort and care. Every inch of the butterflied whole chickens is coated in allspice, thyme, scallions and five-alarm Jamaican scotch bonnet peppers, then the birds are slow-grilled over hot charcoal for two hours. Finally, they are carved to order and served with a heaping portion of fresh plantains, salad, beans, rice and Caribbean hard dough bread. You'll need every bit of those sides to blanch the fire that will inevitably rage in your mouth, too. Daddy O's chicken is not for the faint of heart.
Cheap eats
Harold's Chicken Shack #24
A South Side staple since 1950, Harold's Chicken Shack now has locations across Chicagoland. It's known for impressively tender fried chicken (by the breast, gizzard, giblet, thigh or your favorite combination) that comes smothered with fries and vinegary hot or mild sauce that you'll be glad to sop up with the slices of white bread tucked underneath. Other specialties include fried catfish and perch, and sides like pizza puffs and bags of bite-size fried okra or jalapenos eliminate the possibility of leaving hungry. A full meal will likely run you $8 or less.
Where to chill
Lee's Unleaded Blues
You're just as likely to see men topping off their suspender-and-fur-coat regalia with Fedoras as you are to spot clubgoers sporting White Sox caps at this South Side blues club. Ranging from R&B to reggae to pure blues, the sounds get bigger throughout the night as unexpected guest musicians are invited to "sit in" for a few numbers.
A real live juke joint, Lee's Unleaded Blues resides near virtually nothing, and for those who rarely tread on South Side territory, it's a trek and then some just getting there. But slide into the free parking lot directly behind the club, roll your fine self in by 8:30 p.m., and you're assured cushy seating and a good view of the stage with no cover charge to speak of (though there's an easy-to-fulfill two-drink minimum). While there's a good amount of swank and sass ricocheting between the black-painted and mirror-adorned walls and deep red carpeting, there's a sense of down-home familiarity wafting in the air.
The crowd, which ranges from University of Chicago students to retired folk, shows its appreciation with hip shaking and shimmying, especially when the singers mingle on the floor mid-performance. Lee's Unleaded is no secret to well-informed international travelers and music-loving Chicagoans; the entryway boasts a showcase of framed articles that feature Lee's, including "National Geographic" and "Men's Journal."
In the know-spot
Black Wok
Like many of the newer eateries on East 75th Street, Black Wok brings new flavor to the neighborhood. Specializing in freshness and quality, this establishment lets customers create their own entrees. First, you choose your meat: beef, chicken, fish of the day, shrimp, veggie or a combo. Next, you select your style. Some of the tastier options include black bean and garlic, tomato pepper and kow (broccoli, bok choy, water chestnut and peapods). Then you choose your "base," a grain like brown or white rice, noodles, udon or low mein. Still one final decision awaits: the addition of up to four vegetables.
It's a very Flat Top Grill experience, and one that's certainly delicious. Overwhelmed at all the choices? Order straight from the menu, with picks like fried rice, egg foo young and other standard Asian fare. The portions are hearty, the food lacks the extra grease that seems to plague some stir-fry restaurants and the staff remains friendly and speedy. Best of all, the price is right: Nothing on the menu is more than $9, making it a perfect place to dine with friends on the cheap.