71st bus stop. Photo by Jason Schumer

This shared introduction comes at an interesting time when both South Shore and Woodlawn residents might feel that their neighborhoods are in flux. For some, this was probably always the case, but the recent groundbreaking of the Obama Presidential Center has intensified sentiments that the conditions of these neighborhoods today might be different tomorrow. ‘For better or worse?’ remains the question, but defining either outcome would require an up-to-date understanding of both neighborhoods. For a long time, both South Shore and Woodlawn were characterized by what they lacked, like grocery stores and other neighborhood amenities. Recent developments in these neighborhoods have certain publications crowning them comeback kids. But we know that there were always assets in these neighborhoods, despite what the system deprived them of. Highlighting these assets is the objective of Best of the South Side.

These neighborhoods cradle one of the largest and most gorgeous parks in the city, Jackson Park. South Shore boasts beaches and rich architecture, Woodlawn is dotted with small parks, gardens, and historic buildings. If you step into the South Side YMCA, or the fields along the easternmost edge of Jackson Park on Stony Island, you’ll see people of all ages enjoying Woodlawn’s amenities. This is the case despite narratives that have been created to suggest the park and the neighborhood are “underused” and “under-utilized.” The narrative is a sure contradiction because, if not for the neighborhood’s involvement and strength in numbers, they wouldn’t have been able to win a significant housing preservation ordinance in the face of gentrification. In South Shore, new efforts are ramping up to build people power behind an ordinance of their own, with the same goal in mind: staying in the neighborhood they know and love. 

In 2020, BoSS highlighted the food, jazz, and activism that came out of South Shore and Woodlawn. If BoSS happened in the 1970s, it’d be the same story. Despite changes in population and housing makeup, the culture has always been rich, and that spills out of historic establishments like Daley’s, and the Jeffery Pub. And sometimes the good things don’t have to be housed in a building. Sometimes they’re a table stand on the side of the road, sometimes it’s the simple atmosphere of a park. Sometimes the sights of your morning walk are enough to keep you enamored with a neighborhood forever. These are the feelings of home that one gets when walking through Woodlawn and South Shore. (Malik Jackson)

Neighborhood captain Malik Jackson is the housing editor at the Weekly.

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Best Corner

71st and Jeffery

You know the movies where the actor is going through a crisis and they somehow find themselves in the middle of the street at some point, overwhelmed by the sounds of the city and the people, dodging oncoming traffic and covering their ears from the loud honks of car horns? 71st St. and Jeffery Ave. is that, with added color. 

Though the Jeffery Theater closed down in 1977, people still crowd the intersection of 71st and Jeffery to talk shit, trade squares, and watch the neighborhood boil into one corner. It’s the landing zone for the J14, one of the busiest routes in the city, and the 71, which can take people from the 100s on the Southeast Side to the 69th Street Red Line station. It also houses the Bryn Mawr Metra Electric stop, which gives people a quicker option to get further south or downtown. Because of this, and because 71st St. is one of the more well-resourced commercial corridors in the area, many people find themselves on this corner or at least walking along the adjacent streets on a daily basis. 

There are different scenes for every corner of the intersection. On the northwest corner, there are sometimes street pastors setting up chairs and speakers to preach the word that compels them, which tends to humor others. Ironically, Jeffery Pub is right behind it, which is one of the country’s longest running Black LGBTQ bars. On the southwest corner, people spill in and out of the 71st Street Walgreens, which locks most if not all of their products, from toothpaste to bar soap, behind plexiglass. The southeast corner has one of the most iconic gems of the neighborhood, the Currency Exchange, which has the magical ability to admit customers in a happy mood and send them out much angrier than they were before. The energies spill out onto the street and make for a better melting pot but it’s all love in the end.  (Malik Jackson)

At the intersection of 71st St. and Jeffery Ave., any time of day.

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Best Customer Service

Taco King

Always under shade, you can grab your curbside taco somewhere along 67th St. east of Jeffery Ave., depending on where the King sets up shop.

For most, the blue and yellow sign draping from the foldable table that reads “Taco King” can only be read if you bend over and lean around. Since the sign is too long for the height of the table, the bottom of it is a bit hard to make out. This won’t be a deterrent though, because the smell of shrimp and chicken and the sounds of soul music will be enough to make you stay, and the spread of sauces and lettuce, onion, and pineapple will be enough to kickstart your imagination: “How many tacos do you want?” The King of Tacos, the Taco King, decisively steps away from his grill with his own inquiry. He knows why you’re here, he just wants to know what you want from him. And his tone is almost hurried, like he wants you to get going, even though there’s no one else in line. The music is so loud behind him that he asks you to repeat everything you’re saying, at least once, maybe four times and on the third “Huh?” you can’t help but think, “Maybe that music’s too loud, man.” But it’s okay, because the shrimp is grilled and the sauce is green and from the way the Taco King lays it all on the tortilla, it doesn’t seem like he makes too many considerations for portion size. (Malik Jackson)

67th and Clyde Ave., sometimes on weekdays, often on weekends.

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Best Win

Hyde Park Academy

Schools are some of the most long-standing institutions in the city. Many public school buildings in Chicago are distinctly recognizable within their given neighborhoods. Hyde Park Academy is no exception. Its bold-bodied structure and white facade is highly anticipated when venturing down Stony Island, and the legacies that come from inside are even more treasured, as Gwendolyn Brooks, Donny Hathaway, Minnie Ripperton, and G Herbo have passed through the halls at some point.

Recently, new legacies were kickstarted at the school. As the Weekly has reported recently, Hyde Park Academy was central to the citywide push for the removal of School Resource Officers (SROs) from Chicago Public Schools. Hyde Park voted to remove one of their SROs from the school and use the new funding for a new Dean of School Climate and Culture.  (Malik Jackson)

Hyde Park Academy, 6220 S. Stony Island Ave.

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Old South Shore High School. Photo by Jason Schumer.

(Worst) Repurposing of a School

South Shore High School

South Shore High School’s old building has been standing since 1940. For decades it was an anchor in the community with a vital function: educating youth. It was a place where youth from families around the neighborhood would come to congregate, make new connections and discover their passions. The motions of the twentieth century changed the makeup of the school and the area. White flight, deindustrialization, and divestment are just a couple phenomena that caused South Shore to not only struggle with resources, but school attendance as well. After a series of experiments to keep the school going, the Board of Education voted to phase out the school in 2009, and yet another community anchor would be closed, no longer administering its once vital service. In 2020, City Council approved a plan to turn the old South Shore High School building into a police training facility. In a city where police regularly brutalize Black youth, this seems like the worst idea ever, let alone the antithesis of what the building was created for. These are the metaphors Chicago grants its citizens, with no regard for backlash. (Malik Jackson)

Old South Shore High School, 7529 S. Constance Ave.

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Comfort Station. Photo by Zakir Jamal.

Best Potential

Jackson Park Comfort Station

If you are ever driving east on Marquette to merge onto South Shore Drive, you’ve likely seen what appears to be anything between a rundown rest station to a target for Jackson Park golfers. It’s battered, to say the least. Parts of the roof are practically slipping off. The facade is cracked. Its pillars are collectively on their last leg. 

But under the sun, you can tell what it once was. The tiles that are slipping off are Spanish-style, with a warm terracotta color to them. The details of the exterior are striking. And if you step closer, you can tell that the struggling pillars once had color and structure, like the others that haven’t yet fallen into disrepair. 

The Comfort Station was built in 1912 by D.H. Burnham and Co., which was headed by Daniel Burnham, one of the first city planners in Chicago. It served as a restroom for men and women who’d golf in Jackson Park, but today, unless you’re willing to hop the gate that surrounds it—it has no current use. But that’s the beauty of the structure. It’s been standing long and stable enough for us to know what it used to be, and if the Chicago Park District’s South Lakefront Framework Plan comes to fruition, we might be able to see the building’s future. (Malik Jackson)

Jackson Park Golf Course, 6401 S. Richards Dr., by the 10th hole.

Comfort Station. Photo by Zakir Jamal.
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