In Midwest

If you’re from Chicago you know that when telling a fellow Chicagoan where you grew up, you have to specify which parish you lived by. It’s not enough to say you were born in Bridgeport, for example. 

Chicago has so much to offer. It’s a city of diverse neighborhoods (technically “community areas”) and sub-neighborhoods. It’s an exciting city and offers up a lot of opportunities for real estate investors. And while Chicago may be in a market high, you should know that thereis isn’t just one real estate market in Chicago. There are many markets, and always an area that is hot or up-and-coming. Finding the right one is how you can set yourself up for success. 

Here are some of the best places to buy investment property in Chicago in 2022. 

best places to buy investment property in Chicago

The Best Places to Buy Investment Property in Chicago

I’ve compiled this list using the Chicago community area map. These 77 areas are sometimes interchangeable with neighborhoods, but the “neighborhood” designation isn’t official. For example, there is no official “Ravenswood neighborhood”, but it is an unofficial subset of the Lincoln Square community area. 

More importantly, it’s good to remember that “best” doesn’t always mean hottest or most up-and-coming. It’s where you can find a cheap lead in Chicago, buy a house, and potentially see a return on your investment. It’s best to look at places where you have the most chance of success. 

Humboldt Park

In the public imagination, Humboldt Park is teetering on the line between “don’t go there” and “buy now!” There are still a lot of people who only think of Humboldt Park in terms of its heyday of gang violence in the late 90s and early 2000s. But in my opinion, Humboldt Park is an up-and-coming neighborhood with a ton of real estate potential. 

Right now, prices are slightly higher than the average in Chicago, but nowhere near as high as in neighboring Logan, which is well past up-and-coming and firmly into established and ultra-expensive. That means the boom has to spread, and Humboldt is poised to take advantage of that. There are already new breweries, restaurants, and stores, while still maintaining the vibrant flavor of the neighborhood. 

And, of course, there is the park, a 207-acre lagoon-filled gem. The sheer beauty of this neighborhood, its relative inexpensiveness, and its shared border with Logan Square make this a must-buy neighborhood in 2022. 


If you balked at hearing “Humboldt Park” then you probably spit out your coffee at Englewood. It will never be on a Chicago “hot list”, and is more likely to make a list of “worst neighborhoods in Chicago.” But that’s just looking at the current economics. Englewood offers the smart investor a lot of opportunity. 

The median home value in Englewood is about $79,671—practically a steal. But what might surprise you is that there are some listed at $600,000 and higher. This is because Englewood is a neighborhood that is slowly changing. The “L” stations are being revamped. The food desert is drying up. A new STEM school is helping children reach their potential. 

In Englewood, you can find cheap homes and potentially turn a profit. You don’t have to be in the hottest neighborhood. You just want a situation that is better tomorrow than it is today. Englewood could be just that. 


Avondale is one of those neighborhoods that people don’t really know about. Sandwiched between the river and I-90 and I-94, it’s not really “north side” and not really “west side” either. It’s residential and also kind of a throughway. Though, one would say that it’s conveniently located. 

Because it borders Logan to the north, it’s poised for more spillover. It also touches on Roscoe Village, Lakeview, and North Center. As those areas get more developed, one can expect spillover. 

Houses here are sneakily going for high prices, but there are still deals to be found. This is one of those areas that magazines don’t talk about right now, but those in the know are eager to find properties here. 

The Best Way To Find Leads in Chicago’s Best Places To Buy

So now that you know the best places to buy investment property in Chicago, you need to know how to find quality leads and motivated sellers. In my more than two decades as a real estate investor, I’ve probably tried every way imaginable to find that perfect lead—one that’s low priced, in a great area, and has little competition. I’ve tried everything from going door-to-door to skimming Craigslist. It wasn’t until I invested in an independently owned and operated HomeVestors® franchise that I found the perfect way to get quality leads. 

As a HomeVestors franchisee, I am able to tap into their powerful marketing network—the We Buy Ugly Houses® campaign. It works because everyone in Chicago—from Hegewisch to Rogers Park—knows it. When they have to sell a house fast, for cash, they call HomeVestors and I can get the lead. 

With their proprietary tools, training, and marketing, they help me take out the hardest part of investing in Chicago real estate. I just have to make the right decisions. That’s true no matter what neighborhood—or ward or parish—you’re buying in. 

If you’re considering buying investment property in Chicago, request information about becoming a franchisee today


Each franchise office is independently owned and operated.

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