All cities change, but for those of us who have been in Chicago real estate for a long time, the changes have been dizzying. I got into it in the early ’90s—when the South Loop was still a no-go zone, and the West Loop was all warehouses and packing plants. The idea that those markets would be for millionaires wasn’t on anyone’s horizon.

Things change fast. And if you want to run your investment business right, you have to anticipate and react to Chicagoland real estate trends. You have to know where to make a move, and you have to be ready to move when things change. You don’t want to be thinking about moving into a neighborhood after everyone else has already bought and sold. You have to stay ahead of the curve. 

Here are some of the best neighborhoods to keep your eye on this year. 

Chicago housing market

A Quick Note on Chicago Neighborhood Real Estate

I can always tell when someone is a new investor because they tell me they are looking in Logan Square or Lincoln Park for their next investment. Sure, if you can find a cheap home in those neighborhoods, you have a chance at making real bank. But you probably won’t find one. You might be able to sell a house in that area for a pretty penny, but you’ll also be paying one for it, too. 

If that’s your business model, then that’s perfectly fine. But you don’t always need the “DEAL OF A LIFETIME”. You want homes that you can get for a relatively low cost, fix up, and sell for a profit. That doesn’t always mean investing in the “hottest” neighborhood. It means investing in ones where you can succeed. 

Areas with investment potential aren’t always the “best” neighborhoods—especially in Chicago. You may find an opportunity in what may be considered one of Chicago’s worst neighborhoods. That’s the beauty of this business. 

The Best Places To Look at the Chicago Housing Market

When it comes to finding the best areas in Chicago in which to invest, I recommend looking at a variety of neighborhoods: those that are established, up-and-coming, and even the so-called “worst neighborhoods in Chicago.” If your tried-and-true business model is finding undervalued houses and making a profit, there are opportunities nearly everywhere. 

Washington Park

Washington Park is not a neighborhood that shows up on a lot of tourist guides… yet. For years, it has struggled with crime and a poverty rate below the average of even the surrounding area. And while the corner hasn’t been turned quite yet, there are a lot of signs in its real estate that things are changing. For example, it is part of a coalition of neighborhoods focused on building up transit-oriented neighborhoods, as Washington Park has access to the Green Line and proximity to the South Shore Line. 

Washington Park is anchored by the beautiful, huge, sprawling, and lively park that gives the neighborhood its name. It is always filled with families grilling and playing music. Its lagoons and fields are an anchor for people looking for a fun outdoor life. There are single-family homes with sturdy bones as well as large, stately, limestone multi-family units available.  

It also seems likely (though not guaranteed) that the opening of the Obama Presidential Center in neighboring Jackson Park is going to have a positive and radiating impact on the area. Washington Park is rarely called “up-and-coming”, but this could be a great time to get in on the action before the competition. 


In my experience, Hegewisch (Hegs-wish) might be the least-known neighborhood in Chicago. Tucked in the furthest southeast portion of the city, it shares the longest border with Indiana than any neighborhood. Indeed, people frequently cross over into Hammond to fill up their tanks. 

That’s part of its appeal, to be honest. You are in a completely different world. You’re hard up against the beauty of Wolf Lake, which is wonderful for fishers and hikers, alike. You’re also near a ton of recreation areas and forest preserves. 

The area is also very safe, with a “B” score in crime—comparable to Logan Square and Lincoln Park. Hegewisch is currently a hidden gem. But as more people want to get away from the crowds of the city, this is an area that might be hidden no longer. 

Irving Park 

I’ll be honest: for a long time, Irving Park was one of those neighborhoods that seemed stagnant. I’ve never thought it would be “hot”. But that doesn’t mean it is a bad investment. In fact, it may be just the opposite. 

The areas around Irving Park, especially the Square and Albany Park are either saturated or becoming saturated. So while Irving Park might not be the hippest area, it is a great place for families looking for a home with good schools and near public transit. There are nice, comfortable houses with surprisingly large backyards on pleasant leafy streets. 

Remember, you don’t need the next Wicker Park. You need an area that, for reasons of proximity and history, has a lot of potential. 

The Best Way To Get Houses in Chicago

A wide range of opportunities awaits buyers in the Chicago market but I’ve found that it’s best to find a niche and run with it. The properties that pack the most promise for me sit on the low end of the spectrum. I enlisted some help at the start of my real estate investing career by becoming an independently owned and operated HomeVestors® franchisee. The nationally recognized “We Buy Ugly Houses®” marketing campaign turns up quality leads on distressed properties that I can buy, renovate, and sell with reasonable confidence about returns. With so many Chicago neighborhoods to choose from, I’ve been able to uncover gold among the ruins.

If you’re considering investing in the Chicago housing market, request information about becoming a franchisee today

Each franchise office is independently owned and operated.


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