The other day, I was on an informal virtual happy hour with other Chicago real estate investors when one person brought up Englewood; a sort of nervous titter went through the group. “Who invests there?” seemed to be the unspoken consensus. That’s because Englewood has a reputation for being one of the worst neighborhoods in Chicago. But that doesn’t mean there aren’t opportunities there. 

In fact, what we think of as some of the poorest and “worst” neighborhoods in the city are filled with great people looking to improve their lives and their community. You can be part of rebuilding the community by finding great investment opportunities there. 

Chicago is a city of neighborhoods, some glitzy, some more rough-hewn. But we’re all Chicagoans. And for the smart investor, some of the worst neighborhoods might be your best real estate investment move.

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Why You Could Invest in the “Worst” Neighborhoods in Chicago

To be clear, “worst” here is an economic standard, not a judgment on the people who live there. I grew up in a neighborhood that would have been, at the time, considered one of the “worst” areas. So did my parents. In fact, their neighborhoods were both destroyed by the highways. So I know what it means to have people think your neighborhood is bad. 

But there are ones that are more deficient than others. Most real estate investors don’t want to invest there. They think it is throwing good money in a bad area. But there are a few factors to take into account. 

  1. Neighborhoods don’t always remain static. What’s “bad” today could regrow tomorrow.
  2. You don’t need a neighborhood to turn into Humboldt Park and suddenly become super hot. All you need is marginal improvements in property values to occur. 
  3. There are houses for sale. Foreclosures, abandonments, pre-foreclosures: these neighborhoods have a lot of property. If you can find one that you can afford, fix it up and flip it around. 

That’s the thing about this business. You don’t need to find the one block that’s about to become the centerpiece of the Young Tech Person Who Likes Signature Cocktails archetype. You need to provide people with a good place to live. And you can do that in neighborhoods that have been deprived of investment.

So what does that look like in Chicago? Let’s take a look. 

Finding the 5 Worst Neighborhoods in Chicago 

We’re going to be using the Chicago Data Portal to look at some of the numbers here, with the key factor being houses below the poverty line. This isn’t some kind of objective “worst” but it is a way to look at some of the poorest areas in the city. 


Despite the bucolic name, Riverdale is a hard neighborhood filled with less-than-pleasant industries. It runs up against the shipping canals and is home to the largest water reclamation district in city limits. With a 56% poverty rate, it is by a good margin the poorest neighborhood in Chicago. Its land is largely industrial. 

Why it has some promise:

We’re not going to say Riverdale is poised to break out. But as long as the Port of Chicago is there, there will be jobs. It’s actually located extremely conveniently close to I-94 and the Indiana border. And with 5.8% of its housing stock crowded, there is a need for better housing to give people more room. It’s an area with such little investment that any at all might make a difference to people. 

Fuller Park

This is another neighborhood that a lot of people up north might not have heard of, but everyone has been through it. It runs along both sides of the Dan Ryan and the Red Line and was, in fact, divided in two by this massive highway project in the 1950s. Its population has declined steadily ever since, as the highway prevents a true neighborhood from forming. With a 51% poverty rate, it is not considered a very desirable place to live. 

Why it has some promise:

Fuller Park has been the beneficiary of changes in the way the city runs public housing, transforming from creaky highrises to more livable and people-oriented flats and mixed-income developments. These housing units have been going up and down Fuller Park in the last decade. As more people find out that it is a good area connected to other places, and not one neighborhood split in two, there might be an opportunity to attract a little more money. 


Englewood has a poverty rate of 46%, a per capita income of under $12,000, and a national reputation for being a violent, dangerous place. There’s a reason most investors think they should avoid Englewood. The name alone is synonymous with people’s fears about Chicago. It’s famous for being infamous. 

Why it has some promise:

For one thing, there has been a lot of investment in the area lately. New stores have broken up the food desert. 63rd Street has been transformed. And with a new public STEM academy, students from the area are getting the chances they deserve. And Englewood is a vibrant, lively, wonderful area that has created some of the city’s best artists and musicians. It’s a place where families have lived for generations. Finding a house, and selling it, is not impossible. It’s a way to be a part of a comeback. 

North Lawndale

There’s not a ton of difference between Lawndale and North Lawndale; in fact, most people refer to the two synonymously. But North Lawndale is officially the fourth poorest area in the city, with a poverty rate of 43.1%. Sprawling out on the city’s West Side, it is too far away to be buoyed by the West Loop’s development, and too far north to be impacted by a growing Chinatown. It’s nearly forgotten. 

Why it has some promise:

It’s not forgotten by the people who live there. This is a crowded area, with a 7.1% housing crowded rate, because it is full of families, people looking for a good life for themselves and their kids. The Carole Robertson Center for Learning is proof of this ambition and drive. It is filled with people who demand better housing, and real estate investors are in a good position to give it to them. 

East Garfield Park

Walk through Union Park, at the far end of the West Loop’s famous restaurant scene, away from the million-dollar condos, and you’re soon in a different world. East Garfield Park has been poor for decades, with a 42% poverty rate right now. It’s a place that seems run-down, shaken by the Green Line tracks, filled with rust and empty lots. 

Why it has some promise:

The Garfield Park Conservatory is one of the city’s absolute gems. And all of Garfield Park is home to stunning houses from when this area was vibrant and well-off. There is great property here. It’s right along public transportation. It is an area filled with people who want something better, who want to build this storied area up again. You can be a part of that. 

Finding Property in Chicago’s Poorest Neighborhoods

As we said, there will always be people looking to sell, and you have a chance to buy. But what’s the best way? For obvious reasons, looking on Instagram for real estate isn’t always your best bet. You can find abandoned property and sort through Chicago ownership records, but that is super onerous. The best way I found is to become an independently owned and operated HomeVestors® franchise.

As a franchisee, I get qualified leads from people who call HomeVestors®. Probably everyone in Chicago has seen the “We Buy Ugly Houses®” advertisements. So, when someone in these neighborhoods needs to sell quickly, chances are, you’ll get a lead. You can evaluate its potential and make a decision concerning whether or not this is a good buy for your business.

So maybe these neighborhoods aren’t on your radar. Maybe somewhere else in the city is. But you should know there is opportunity everywhere in Chicago, from the hottest neighborhoods to the ones no one is looking at. If you want a chance to build communities and your business, request information about becoming a franchisee today. It’s your best move. 


Each franchise office is independently owned and operated. 


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