What’s Right With Chicago: A Black Man’s Guide to America’s Greatest City

Recently, the President of the United States decided to declare war on Chicago. Now, it’s been a minute since I took 8th-grade civics, but I don’t know if presidents declaring war on things has worked out for them. I mean, we had a war on drugs and a war on poverty, and if we’re being honest, drugs and poverty won. So if this guy wants to declare war on Chicago, y’all probably need to learn the “Super Bowl Shuffle” as the new national anthem because Chicago is gonna win. 

While this is ostensibly about crime and a cover for draconian immigration enforcement efforts, it’s really an attempt to malign a multi-racial, multi-ethnic, and multi-cultural city by insinuating that those things create dangerous living conditions. In the shorthand of political language, “crime” has always been a proxy for “Black people,” and thus saying you’re going to be “tough on crime” is code for making sure you keep “the Blacks” in their place. 

Nosey folks in Ohio with nothing to do but use their Skyline Chili-stained fingers to type out invectives about my neighbors. People in Florida dodging hurricanes and meth addled alligators with equal urgency, who somehow deputized themselves as freelance criminal profilers. Out-of-towners who think that, because they went to a Giordano’s once in 2004, they’re suddenly urban policy experts whenever “Chicago” hits the chyron on cable news. They’ve never ridden (or bought socks on) the Red Line, never drove down Lakeshore Drive at sunrise after being out all night chatting up someone special at Slick’s Lounge, never been cussed out at a Harold’s for not knowing how to order when they got to the window, but somehow they’re qualified to tell me what it’s like to live here.

So let me go ahead and set the record straight: I’m from Newport News, Virginia, but Chicago is home. I’ve been here almost two and a half decades now, and in that time, I’ve built a career, a family, and a life that I sometimes pinch myself over because I can’t believe I’ve been so blessed. Does it have problems? Of course. Name me a city of three million people that doesn’t. If you cram all these souls into one place, make them share a finite set of resources, and ask everyone to get along, issues will naturally arise. Nowhere is perfect. But are the cons so heavy that they outweigh the pros? Absolutely not.

To borrow from Common, “At times I contemplate moving to a warmer place, then the lake and skyline give me a warm embrace.” That’s it right there. Instead of listening to talking heads who wouldn’t survive a cookout on the West Side, I’m going to tell you, as a Black man, what’s right with Chicago. Not the touristy stuff they put in the brochures or the human interest stories you see on WGN.  But the things that make this city feel so unapologetically Black, real, and give it its unmistakable vibrance.

So, next time one of the people around you shapes their face to talk sporty about my city or gets behind a keyboard to besmirch DuSable’s jewel on the lake, here are ten things you can tell them about that make this place the kinda town that’ll never ever let you down.

1. Promontory Point

Tourists get shuffled off to Navy Pier to buy overpriced popcorn, eat Bubba Gump shrimp, and snap selfies with the Ferris wheel. But if you live here, you know better. If you want the most breathtaking view of the skyline, where the city seems to rise up like it was a Hebru Brantley mural commissioned just for you, you go to Promontory Point. “The Point” is a Chicago rite of passage: a barbecue, a bike ride, a late-night stroll along the lake. It’s where you see the diversity of your neighbors up close, families laid out on blankets, joggers striding by, uncles with the folding chairs and coolers full of the yes-yes-y’all, young lovers figuring it out with the city lights as their backdrop. 

You don’t need to RSVP. You don’t need to be on a boat tour. You just show up, and it’s yours.

2. Midway Airport

This one might surprise people. O’Hare is the international hub that hogs the spotlight, but ask anyone who flies regularly, and they’ll tell you, Midway is the move. But Midway is also, quite unofficially, the Black airport (say I’m lyin’).

No 45-minute hikes to your gate. No endless supply of fast casual chain restaurants that serve adults chicken fingers. Just a quick in-and-out with a straight shot to or from downtown, TSA lines that move faster than the Costco checkout, and gates that don’t require you to pass through four different zip codes to find your flight. Midway is where you bump into at least three exes, a former coworker, and that dude you bought socks from on the Red Line that one time, all before you grab your Home Run Inn pizza by B17. It’s chaos, but it’s our chaos, and it works.

3. George Daniels

The elected mayor changes every few years and, no matter who they are, they stink. But the real mayor of this city is George Daniels. His face is a coupon, and if you’re Black in Chicago and you love music, you’ve either met George or you’ve felt his influence. George’s Music Room, his West Side record store, was more than a shop; it was a temple. Everybody passed through: DJs, producers, church kids buying their first gospel record and their first Twista record, crate diggers searching for the perfect sample. Daniels is the living archive of Chicago’s musical soul and history. Real spit, did you know he took Minnie Riperton to prom back in the day? That’s not folklore, that’s fact. He showed me the picture one night at 16th Street Lounge. Every great city needs a constant elder, someone who carries the cultural memory, and George Daniels is ours.

4. People That Went to Whitney Young

Chicago has its own caste system, and it starts with high school. The first thing people will ask you is, “Where’d you go?” And the second thing they’ll do is judge you based on your answer. Whitney Young people, though? They’ll save you the trouble. You don’t need to ask them. They will tell you, unsolicited, that they went to Whitney Young. They’ll tell you you should’ve been a Dolphin. And then they’ll remind you of everybody else who graduated from Whitney Young.

But it’s not just about Whitney Young. It’s Kenwood. It’s Lane Tech. It’s Simeon. It’s Morgan Park. It doesn’t matter because they all say it with their chests. Each high school is its own little universe, and people’s pride in their alma mater is unmatched. It’s not shade, it’s culture. It’s how Chicagoans know where you fit in the story.

5. The Food at Home Depot

Yes, you read that correctly. The Home Depot. In Chicago, you can go to pick up a hammer drill, some lightbulbs, and a Polish sausage with grilled onions and extra peppers all in the same trip. Some Home Depots have taco stands. Others have ribs. Don’t question it, just accept it. Quality Chicago food is everywhere. It’s not limited to restaurants with tablecloths. It’s not confined to “foodie” neighborhoods like Fulton Market. You can step into a Home Depot and have a meal that could stand up to any street food culture in the world (New Yorkers, your halal carts are on notice). The city turns mundane errands into accessible culinary adventures. That’s the magic.

6. The Silver Room

The Silver Room is more than a store; it’s a movement. Eric Williams built more than a retail space; he built a cultural anchor. It’s where you go for jewelry, clothes, art, but more importantly, it’s where you go for community. If you ever went to The Silver Room Block Party, you already know: it was the Black summer festival. A Chicago Coachella where the spirit of Afro-liberation found itself combined with an eclectic sense of belonging that lacked all pretense. It was a gift to be there and just be. The Block Party might be gone, but the energy lives on. Anytime you see a flyer that says “The Silver Room Presents,” you know you’re in the right place. Even if you don’t know nobody else in the room, those are your people.

7. The Gym Shoe Sub

Why does this sandwich exist? Nobody knows. Why is it called a “gym shoe”? Nobody can explain. What’s in it? Steak, gyro meat, corned beef, lettuce, tomato, cheese, onions, Tzatziki sauce, basically everything the guy at the counter could think to throw on a bun. And yet, somehow, like the diversity of the neighborhoods in this city, it just works. It’s messy, it’s overstuffed, it’s unapologetic. It is woefully inappropriate, but entirely necessary. In other words, it’s Chicago if Chicago were a hood sandwich. It’s the kind of food that shouldn’t exist, but because it does, you realize no other city would’ve been gully enough to invent it.

8. The Blues

Every genre of popular music owes a debt to its progenitor, the Blues, and the Blues owes its second life to Chicago. When Black people fled the deep South in droves during the Great Migration, they brought the Delta with them, and Chicago electrified it then turned it up to eleven. Muddy Waters, Howlin’ Wolf, Willie Dixon, Buddy Guy, they turned the city into the epicenter of American music. Rock, soul, R&B, hip hop, they all carry Chicago Blues in their DNA. The Blues here isn’t just about heartbreak; it’s about survival, testimony, and turning struggle into sound. It’s also a reminder that we live in a place that loves Black things but doesn’t always love Black people. That’s Chicago in a riff.

9. The Winter

I said it. Winter is what makes Chicago Chicago. Yeah, it’s colder than a pimp’s heart on Madison. Yeah, the sun sets at 3:15 in the afternoon. Yeah, you’ll feel a gust of wind cut through every layer of your clothing like a hot knife through Crisco. But here’s the secret: winter is when locals thrive. Tourists are gone. Traffic is lighter. It’s house party season, spades-in-the-basement season, karaoke night season. It’s when you kick it with the people you actually want to kick it with, not just folks you find yourself outside with. It’s when the food tastes even better because calories don’t count in negative windchill. Shark’s chicken, Italian Fiesta pizza, JJ Fish; winter gives you permission to lean all the way in. The city’s stripped down to its essentials, it’s too cold to be pretentious, and what’s left is real community.

10. The West Side

Only because I feel like if I don’t talk nice about them, they might come after me. 

Now That You Know…

Chicago ain’t perfect, but perfection is overrated. What we have is authenticity. What we have is resilience. What we have is a city that doesn’t need your approval because it’s too busy living. And it’s Black AF.

Outsiders love to harp on the violence, the politics, the weather, but they’ve never held hands on the lakefront path on a summer night. They don’t know about watching a White Sox game sitting between a Nobel Prize-winning economist and a truck driver at Jimmy’s Woodlawn Tap. They don’t know the taste of a sweet steak from Home of the Hoagy or the sound of Deep House and Disco cutting through the air at the Chosen Few Picnic. They don’t know about bid whist in the basement when the Bulls game is on in the background. They’re stuck in traffic coming from O’Hare, shook because they’re worried that their Airbnb in Lakeview might be dangerous, like a goofy.

That’s Chicago. Messy, magnificent, maddening, magnetic. And it’s ours. So, to everyone in Dayton, Orlando, or wherever else who wants to make Chicago your boogeyman for clout: respectfully, STFU. Unless you’ve lived it, loved it, and frozen your eyelashes off walking to catch the J14 bus in February, you don’t get a say.

Chicago is America’s greatest city. And if you don’t believe me, that’s fine. More Polishes at Home Depot for me.

Corey Richardson is originally from Newport News, Va., and currently lives in Chicago, Ill. Ad guy by trade, Dad guy in life, and grilled meat enthusiast, Corey spends his time crafting words, cheering on beleaguered Washington DC sports franchises, and yelling obscenities at himself on golf courses. As the founder of The Instigation Department, you can follow him on Substack to keep up with his work.

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