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Author: Mark Ainely | Partner GC Realty & Development & Co-Host Straight Up Chicago Investor Podcast
Do you ever feel stuck when trying to pick where to buy rental property around Chicago?
You see one suburb with cheap homes. Another with high rents. Some with confusing rules.
It can feel like throwing darts blindfolded.
You are not alone. Every week I get calls from investors asking the same thing:
“Where is the best place to buy in the Chicago market?”
Today, I’ll give you the answer. And I’ll show you why most people fail, while our clients win.
In this article I will break down more around the Chicago suburbs and we will get into the 77 Chicago neighborhoods in a future article.
The Big Problem
Most investors think buying in Chicago’s suburbs is easy but that can be a wide variety of investments. Just find a cheap house, fix it up, and rent it out.
But here’s the truth:
Some towns drain you with rental license fees.
Some suburbs bury you with high property taxes.
Some counties (like Cook) have strict rules (RTLO) that trip up landlords.
Some school districts keep good tenants long-term, while others send them running.
One wrong move, and your “great deal” turns into a money pit or becomes an investment that is not in any way passive.
Why Other Advice Fails
You may have heard “buy cheap in Harvey” or “look in Country Club Hills, it cash flows great.”
Bad advice.
Sure, the homes look cheap. But the hidden costs, licenses, inspections, high taxes, Section 8 headaches, eat your profits.
Many towns even change rules mid-game, leaving you with new costs you didn’t plan for.
Most so-called “gurus” don’t warn you about this. Why? Because they don’t manage properties here. They don’t see the pain investors face every day.
We do.
In addition to being a Property Manager, I have been an investor for 23 years as well and i have bought right but also bought wrong!
Check out the 1000, $1000 mistakes i made doing 482 BRRRR Properties in Chicago where I share all the mistakes I made. Watch Now!
Our Proven Answer
At GC Realty & Development, we manage over 1,400 rental homes across Chicagoland.
We’ve seen every market. Every suburb. Every tenant problem.
We know which areas help you build wealth, and which ones wreck your returns.
We also run Chicago’s #1 real estate investment podcast, Straight Up Chicago Investor. Every week we share deep insights on neighborhoods, laws, and deals.
And we know rental license programs, Evanston’s requirements, and Cook County RTLO rules better than anyone. Because we deal with them daily.
That’s why investors trust us to guide them.
Where Investors Win
Let’s talk suburbs. Some shine. Some sink.
DuPage County – Safe and Steady
I can group this in a pretty general way. It is tough to lose in DuPage but also tough to find a deal at times where the numbers makes sense.
But that is what makes it that much better of an investment.
Why it wins: Great schools. High incomes. Stable tenants. Easier evictions than Cook County.
No rental license in most towns. (Naperville, Wheaton, Glen Ellyn, Lombard, Elmhurst, etc.)
Investor bonus: Low rental supply means less competition.
- Example: Buy a house in Naperville. Families stay for years. You avoid costly turnover.
Hanover Park – A Mixed Bag
In Carol Stream or Roselle school districts (DuPage side), tenants stay longer.
In Schaumburg school district, values are higher but still solid.
- Lesson: School districts matter. The same town can give you very different results.
Glendale Heights – High Fees, But Strong Renters
Yes, licenses cost more here.
But many renters move in because nearby towns are too pricey.
Bonus: South side of town closer to North Ave ties into Glen Ellyn schools, which boost long-term demand.
Northwest Cook County – Strong and Growing
Think Arlington Heights, Schaumburg, Hoffman Estates, Elk Grove, Des Plaines, Rolling Meadows, Des Plaines, Palatine.
Why it wins: High incomes. Strong retail. Ongoing development.
Downside: Rental licenses + Cook County RTLO. But if you manage well, still great long-term plays.
- These towns are our second most conservative pick, right behind DuPage.
Near West Suburbs – Close to the City, Big Potential
Berwyn: No rental license. Great deals. Tops our list.
Brookfield: No license. Great schools. Close to the zoo and Metra.
Oak Park & Forest Park: Medical students and city commuters rent here nonstop.
Cicero: Solid rents but messy city hall at times especially if you are doing larger rehabs.
- Buy in the right pocket here and you’ll always find tenants.
South Suburbs – Mostly Stay Away
High taxes. Tough rules. Too many headaches.
But there are pockets of gold:
Flossmoor & Homewood: No rental license. High rents. Families pay a premium for great schools.
Olympia Fields: Rare rentals but strong if you find one.
Glenwood: Lower taxes than neighbors, easy to work with.
- Compare this to Harvey, Ford Heights, and Country Club Hills, where investors drown in fees, crime, and Section 8 red tape.
Southwest Suburbs – Good If You Follow Rules
Alsip, Oak Lawn, Orland Park, Tinley Park.
Strong rents, good tenants.
But heavy on rental license programs.
Example: Oak Lawn requires quarterly pest control, unique and costly if you don’t know upfront.
Will County – Investor Friendly
Frankfort, Mokena, New Lenox, Bolingbrook, Romeoville.
Lower property taxes than Cook.
Easier landlord rules.
Tenants stay longer.
- Romeoville and Bolingbrook have rental licenses, but they’re fair and easy to handle.
Kane County – North vs. South
North Kane: Elgin, Carpentersville, Dundee. Easy to do business. Only Elgin/Carpentersville have licenses.
South Kane: Aurora. Parts are strong (near Rte 59 & Orchard Rd). Downtown Aurora? Avoid.
McHenry County – Simple and Attractive
Algonquin, Huntley, Woodstock, Lake in the Hills.
No rental license requirements in most suburbs.
Easy to run rentals.
Good long-term growth potential.
Becoming most affordable across Chicago MSA
Proof It Works
Our investors who buy in places like Naperville, Schaumburg, and Oak Park enjoy:
Lower turnover.
Higher tenant quality.
Stronger long-term value.
Those who bought in Country Club Hills, Harvey or Ford Heights? They face:
Empty homes.
Section 8 battles.
Endless rental license fees and inspections items.
We’ve seen both sides. And we know which road leads to wealth.
The Cost of Not Checking With Someone Like Us
Investors often forget the fun part is buying the property and the real work is in the ongoing management for year.
The money is made long term no matter how well you bought.
Talk with GC Realty & Development or a professional property manager to learn what the real estate brokers don't know about the long term game
Tough to make money on rentals under 100k in the Chicago market
Get someone like us involved sooner then later even if you plan to self manage, use us for street knowledge.
Conclusion
As I wrote this, I realized I didn’t note many areas where I’d totally recommend against investing in. It all depends on what type of investor you are.
On the investment-style scale, you’ll find pockets for both the Super Conservative and the High Risk with plenty of opportunity in between.
You’ll need to take many factors into account when buying a property in the Chicago market. Two big ones to consider: laws on the city and county levels based on location and the home’s age. These will impact what your next 10 years of capital expenditures looks like.
No matter how bullish I may be on an area, you must consider each opportunity on a case-by-case basis. Much of it comes down to locating a good deal and more importantly knowing what a good deal looks like. Your Realtor and the property managers at GC Realty & Development can help break this down for your personal approach.
GC Realty & Development can help you with property management, but we like to be along for the entire journey to offer advice on where and what to buy. Our brokerage team can even represent you during the purchase. Reach out today so we can further discuss your plans for investing in the Chicago market.
