Anyone who knows me knows that I love Chicago.
I was born in Chicago, lived most of my life in the city, and have never lived more than 35 miles outside the city.
I love Italian beef.
Of course, I love the Cubs.
I even love O’Hare Airport because I can use my Chase Sapphire Reserve points for free flights anywhere in the world.
Why am I talking about my love for Chicago?
Because I regularly get questions like this from newbie real estate investors:
“What markets are the best markets to invest in right now?”
Or:
“Should I invest in Chicago rental properties?”
I’ll never tell you what you should or shouldn’t do. We all need to do our homework and take responsibility for our choices.
But, I can give you some insight as to why I invest in Chicago.
Whether you have any interest in Chicago or not, you should get some ideas on how to evaluate markets for yourself.
Let’s get to it.
What real estate markets are the best markets to invest in right now?
This question comes up a lot when people start thinking about investing in real estate.
The thing is: there’s no right answer.
You might talk to 10 different investors with 10 different ideas on the best markets. No two investors evaluate a market (let alone a specific property) in exactly the same way.
Some investors rely heavily on analytics. Even amongst these investors, you’ll get a difference in opinions. One investor may prefer quickly appreciating markets. Another investor may target cash flow.
I like investing in Chicago because it’s a strong cash flow market. Cash flow is king, after all.
Other investors prefer to trust the “feel” of a neighborhood over data. These investors typically invest locally and have an intimate knowledge of each block in the area.
Through life experience, they have a good sense for what properties in their area will perform well.
Personally, I combine both approaches. I look to local data and trust my common sense and life experiences.
One of the reasons I prefer to invest in my local market of Chicago is because I’ve lived here my whole life.
Not only that, I lived for years in the primary neighborhood I invest in.
I know where the best restaurants and coffee shops are. I’ve experienced what the commute is like. There’s not a park or a playground that you could name that I haven’t been to with my kids.
I keep tabs on developments and improvements in the area. I talk to friends and other local investors.
Plus, I try to be a good steward for the buildings I own. They were built long before me and will be here long after I’m gone.
Because I am personally connected to the neighborhood, I feel a certain pride and responsibility to do my part.
Add it all up and I believe that I have a hometown advantage over outsiders who look at data but don’t know the neighborhoods and the tenant pool like I do.
The funny thing is most national investors want nothing to do with Chicago.
If you read enough blogs or listen to real estate podcasts like I do, national investors have tended to shy away from the Chicagoland area.
There has been a preference to invest in faster appreciating metros, like in the sun belt area.
By the way, I’m totally cool with national investors targeting other parts of the country. That leaves more opportunities for me.
Before you blindly follow what “everyone else” is doing, I encourage you to do your own research and trust your own instincts.
Here’s an example to illustrate what I’m getting at.
If I asked you what housing markets currently have the fastest selling homes, what would you guess?
Phoenix?
Charlotte?
Tampa?
Dallas?
Nope.
Milwaukee is first.
Chicago is second.
Be honest, did Milwaukee jump to your mind? What about Chicago?
My guess is you ignored the Midwest entirely.
If that was your initial thought, you might be surprised to learn that the Midwest has 12 of the fastest selling metros in the country.
On top of that, 6 of the 12 fastest selling metros are in the Midwest.
Here’s a breakdown from a recent report from Realtor.com on the fastest selling metros:
Even as the national housing market slowed to a crawl in August, a handful of metros, half in the Midwest, defied the trend with the fastest-selling homes in the U.S.
The typical U.S. home waited for a buyer for 60 days, a full week longer compared with a year ago, according to the August 2025 Housing Market Trends report from Realtor.com®.
Yet in Milwaukee the median for-sale property remained unsold for just 32 days—roughly half the national days-on-market figure for August, making it the fastest-selling metro among the top 50.
Notably, of the 12 metros with the lowest median days on market (below 40), six were located in the Midwest, three in the Northeast, and three in the South.
As an investor in, and resident of, the Chicagoland area, it did not surprise me that Chicago is the second fastest selling market.
Anecdotally, I have plenty of friends and family currently looking for homes. There is very little inventory and high demand.
That means quality homes sell quickly and for a premium.
If you’re not overpaying, you’re not playing.
I don’t need studies like this to convince me that the Chicago market is hot.
That’s not good news if you’re a new investor trying to break into Chicago.
However, if you already own property in Chicago and are ready to sell, you should be able to make a hefty profit.
How about another recent study highlighting why investing in Chicago may not be a bad idea?
In another recent report from GOBankingRates, Chicagoland dominated a list of the top 50 “safest, wealthiest” places to live in the country.
A Chicago suburb was the number one city on the list. Also, Chicagoland claimed 12 of the top 50 suburbs in the country. That’s just about 25% of the top spots on the entire list.
In total, 7 of the top 10 suburbs were located in the Midwest:
- Western Springs, Illinois
- Lexington, Massachusetts
- Winchester, Massachusetts
- Whitefish Bay, Wisconsin
- Huntington Woods, Michigan
- Ottawa Hills, Ohio
- Winnetka, Illinois
- Kenilworth, Illinois
- University Park, Maryland
- Upper Arlington, Ohio
So, what’s the point?
When I see data like this, it gives me confidence in my investments in the Chicagoland area.
Having 12 of the top 50 “richest and safest” suburbs in the entire country nearby reassures me that Chicago is still a major economic hub. That means lots of good paying jobs and economic diversity in the area.
That, in turn, leads to a deep tenant pool of young professionals who want a part of the action. These young professionals want to rent apartments in trendy areas, such as I where I invest.
Do reports like this mean Chicago is definitely a good market for you to invest in?
I can’t answer that for you.
What I can tell you is that I certainly plan to keep investing here.
Historically, Chicago’s real estate market is often described by experts as a “mature market.”
That means property values have steadily risen over time, but you don’t typically see major swings in value in either direction.
In other words, you may not experience 30% annual appreciation, as was experienced in places like Tampa and Phoenix during the pandemic.
At the same time, you won’t see double digit declines, like we’re currently seeing in some other cities.
This reality played out during the pandemic years. Chicago’s market did not appreciate as fast as other areas nationally. However, as those markets cooled off during the past couple of years, Chicago has stayed red hot in comparison.
In fact, for the past couple of years, Chicago has been one of, if not the, fastest growing markets in the country (alongside New York).
So, what does all this data suggest?
Should you rush off to invest in Chicago?
There’s no right or wrong answer.
I’m certainly not trying to convince you to invest in Chicago.
It would be better for me if national investors continued to shy away so I can scoop up more undervalued properties in good neighborhoods.
The bottom line is that as investors, we are all making the best decisions we can based not only on the available data, but also our own common sense.
I would certainly avoid relying on AI or a single Google search to find “the best markets.”
Keep in mind that within every major market, there are numerous submarkets. You may not realize that if you only looked at city-wide data.
As much as I love the city, I would not invest in every Chicago neighborhood. I focus on 4-5 neighborhoods that I know well.
The data didn’t lead me to that conclusion. Living in different neighborhoods and experiencing daily life convinced me where I should invest.
I support my investment choices with the available data, but I don’t ignore my common sense and personal experiences.
When you are choosing between markets, do your own research.
But, don’t ignore your common sense.
Investors, how do you balance the data with your own experiences?
What factors are the most important to you?
Let us know in the comments below.
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