You can't talk about the South Side without talking about 63rd Street. It’s impossible. Stretching from the lakefront all the way west past Midway, 63rd Street in Chicago acts as a sort of jagged spine for dozens of neighborhoods that couldn't be more different if they tried.
Honestly, most people who don't live here only know it from news snippets or maybe a quick drive to the airport. That’s a mistake. You’ve got the lush, academic intensity of Woodlawn on one end and the frantic, suitcase-dragging energy of West Elsdon on the other. It’s a lot.
What Most People Get Wrong About 63rd Street
If you look at the headlines, you’d think 63rd Street is just a cautionary tale. It isn't. While the street has definitely seen its share of disinvestment—especially after the 1968 riots and the subsequent "white flight" that gutted the local tax base—it’s currently a massive laboratory for urban renewal.
Take the Woodlawn section. For decades, the corner of 63rd and Cottage Grove was defined by the presence (and eventual demolition) of the Green Line "L" tracks that used to extend further south. Today, it’s the site of the Woodlawn Station development. This isn't just another boring apartment complex; it’s a $48 million mixed-use project that actually prioritized keeping long-term residents in the area.
People assume the whole stretch is a "food desert." That's a lazy trope. While access to high-end organic kale might be sparse in certain blocks, you have spots like Daley’s Restaurant. Daley’s has been around since 1892. Think about that. It’s older than the "L" itself. When you sit in a booth there, you aren't just eating breakfast; you’re sitting in the oldest restaurant in the city, surviving through the Great Depression, two World Wars, and the total transformation of the South Side.
The Transit Connection Nobody Talks About
The 63rd Street bus (the #63) is a beast. It runs 24/7.
Why does that matter? Because for thousands of Chicagoans, this street is the only way to get to work. It connects the Red Line and the Green Line, creating a transit bridge that allows someone living in Englewood to get to a job at the University of Chicago or even out toward the suburbs.
The Green Line's 63rd branch is a survivor. Back in the 90s, the CTA almost shut the whole thing down. The community fought back. Hard. Now, the stations at Halsted and Ashland are anchors. They aren't just places to wait for a train; they are literal lifelines. If those stations had vanished, the economic vacuum would have been total.
The Cultural Weight of Englewood and West Englewood
You can't mention 63rd Street Chicago without diving into Englewood. It’s complicated. It’s a place where the architecture tells a story of 1920s grandeur—think the old Southtown Theatre—hidden under layers of modern struggle.
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But look at the Go Green on 63rd initiative. This is a real, boots-on-the-ground collaboration between groups like Inner-City Muslim Action Network (IMAN) and Teamwork Englewood. They aren't waiting for a downtown savior. They’re building a fresh market, a housing project for returning citizens, and a health center right on the corridor.
It’s about "regenerative development." That’s a fancy term for making sure the people who stuck it out during the hard years actually get to enjoy the good years.
- The 63rd Street Beach: A massive, historic pavilion at the east end.
- The Midway Plaisance: Just north of the 63rd street corridor, connecting Washington and Jackson Parks.
- Marquette Park: A massive green space further west that hosted Martin Luther King Jr. during the Chicago Freedom Movement.
From the Lake to the Runways
The vibe shifts once you cross Western Avenue. Suddenly, the residential lots get tighter, the signage shifts to Spanish, and the smell of aviation fuel starts to hit.
West 63rd Street near Midway Airport is a different world. It’s blue-collar, busy, and remarkably resilient. Here, the street serves as the southern border of the airport. You’ve got plane spotters parked in gravel lots and small bungalows where the windows rattle every time a Southwest flight takes off.
It’s one of the few places in the city where industrial logistics and quiet family life live in such a weird, tight proximity. You’ll see a massive freight truck turning a corner next to a kid on a bike heading to a local panaderia.
Why the Obama Presidential Center Changes the Math
We have to talk about the "Obama Effect." With the Obama Presidential Center going up in Jackson Park, the eastern tail of 63rd Street is seeing property values skyrocket.
Is that good? It depends on who you ask.
For homeowners in Woodlawn, it’s a windfall they’ve waited fifty years for. For renters, it’s terrifying. The City of Chicago had to pass the Woodlawn Housing Preservation Ordinance specifically because of this. It’s a legal guardrail intended to prevent the 63rd Street corridor from becoming another gentrified playground that pushes out the very culture that made it famous.
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The Jazz and Blues Ghost Map
If you could see through time, 63rd Street would be glowing. In the mid-20th century, this was a rival to Bronzeville for nightlife.
The street was lined with clubs. We’re talking about the kind of places where legends would play until 4:00 AM and then go get eggs at a 24-hour diner. While most of those physical buildings are gone—replaced by vacant lots or new retail—the DNA of that era is why the South Side still feels like the cultural heart of the city.
The jazz didn't die; it just moved into the churches and the community centers.
Modern Realities: Safety and Growth
Let's be real for a second. Safety is a topic that comes up when people Google 63rd Street. It’s a valid concern in certain stretches where systemic poverty has led to high crime rates.
But treating the entire 10-mile road as a "no-go zone" is just factually wrong. It’s a patchwork. One block is a quiet, tree-lined stretch of renovated greystones. The next might be a vacant lot. The next is a thriving charter school.
The Chicago Police Department’s 7th District (Englewood) is headquartered right near 63rd and Loomis. There’s a massive push for "community policing," though the relationship between the residents and the badge remains, predictably, tense.
Actionable Insights for Navigating 63rd Street
If you’re planning to visit, invest, or just pass through, you need a strategy that goes beyond a GPS.
For the History Buff:
Start at the 63rd Street Beach House. It was built in 1919 and looks like something out of the Mediterranean. From there, head west into Woodlawn. Check out the site of the old 63rd Street "L" terminal. It’s a lesson in how cities can disappear and then rebuild.
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For the Foodie:
Skip the chains. Go to Daley’s Restaurant for the history. Then, head west to the Mexican bakeries near Midway. The contrast in flavors is the story of Chicago in a nutshell.
For the Investor:
Look at the Opportunity Zones. The city is offering massive tax incentives for businesses that move into the 63rd and Halsted area. But come with a plan that includes the community. The days of "top-down" development without local input are over in this part of town.
For the Commuter:
The #63 bus is your best friend if you want to see the city's transition in real-time. Start at the lake and ride it all the way to Midway. You will see the entire economic spectrum of the South Side in a 45-minute ride. It’s better than any museum tour.
The Future of the Corridor
63rd Street isn't going back to what it was in the 1950s. That version of Chicago is gone.
Instead, it’s becoming a "hub-and-spoke" model. The intersections of 63rd/Cottage Grove, 63rd/Halsted, and 63rd/Pulaski are the new anchors. Between those anchors, you’re seeing a mix of urban farming, tiny home experiments, and massive logistics centers.
It’s gritty. It’s loud. It’s sometimes frustratingly slow to change. But 63rd Street Chicago remains the most honest reflection of the city’s struggle and its potential.
To truly understand this street, you have to look past the empty lots and see the foundations. The infrastructure is there. The history is there. And increasingly, the capital is moving back in. Whether that capital serves the people already there or replaces them is the next great Chicago story.
Stop by the 63rd Street Beach Pavilion during a sunrise. Walk through the Woodlawn corridor on a Saturday morning when the sidewalk is busy. Drive past Midway when the planes are landing low over the rooftops. You’ll realize 63rd Street isn't just a road; it’s a cross-section of the American dream, stalled and restarted, over and over again.
Next Steps for Residents and Visitors:
- Check the Chicago Department of Planning and Development (DPD) website for updates on the Invest South/West initiative specifically targeting the 63rd Street corridor.
- Support local vendors at the 63rd Street farmers markets during the summer months to directly contribute to the local food economy.
- Use the CTA's "Train Tracker" for the Green Line if you’re exploring the Woodlawn or Englewood sections, as headways can vary during off-peak hours.