Where the cash flow actually is in the Chicago south suburbs right now

Question

I manage rentals across the south and southwest Chicago suburbs, and the markets that keep producing steady cash flow are the ones a lot of out of state investors skip.

A few I would point newer investors to:

Matteson: single family and small multifamily at accessible entry prices with steady rental demand.

Tinley Park and Orland Park: strong demand and easy access to I-57, I-80, I-294 and Metra, which keeps vacancy low.

Will County and the north end toward Harvey and Markham: lower entry prices if you want higher yield and can manage a bit tighter.

The fundamentals that matter most out here are honest vacancy and maintenance underwriting, and picking a market near job access and transit. Happy to compare notes with anyone buying or operating in the area.

Mike Fisher · Answer

Aaron, thanks, glad it helps on the lending side.

Sean, same here. Inventory is thin, and widening the radius works as long as you underwrite each town on its own taxes and licensing rules instead of carrying over the numbers from the last one.

Timothy, Oak Lawn and Palos Park are familiar ground. I stay on the Illinois side, so I cannot speak to Crown Point firsthand, but I hear the tax point from investors who own over the line.

Alex S. · Answer

The thing that gets people on Will County is that the assessed value often resets to your purchase price after the sale, so the taxes in the current listing can be way off from what you will actually pay. Rerun your numbers with an estimated post-sale tax bill (purchase price x the township's composite rate from the county treasurer site) before comparing it to a Cook County deal, where the reassessment cycle behaves differently. Also check whether the seller had a homeowner or senior exemption on it - that alone can hide a few hundred a month of cash flow.

Mike Fisher · Answer

Thanks Crystal, that is an important catch and I should have flagged it. Anyone looking at Markham, or any village out here, should call the building or licensing department and confirm single family rentals are allowed and licenses are being issued before writing an offer. It changes town to town.

Hossein and Alex, agreed on taxes. The listing sheet bill is almost never the bill you will pay. Rerun it at your purchase price, back out any exemptions the seller had, and the deal that looked better on paper sometimes flips.

Crystal Smith · Answer

I would stay away from Markham for single family rentals. Last I checked the village had a moratorium on single family rentals and were not issuing any licenses

Hossein Sharifi · Answer

Good list. Building on the licensing point, I'd check each town's rental registration and inspection rules and its property tax rate before running numbers. Cook vs. Will County taxes alone can swing cash flow a lot on the same rent.

Timothy W. · Answer

Hang on - Mike Fischer. If you've been in construction in the Southwest Suburbs for over 30 years, you might know my dad. Phil Wieneke. He owned Wieneke Construction. Brown trucks with a big yellow W on them. We were Oak Lawn then Palos Park based for a long time.

Timothy W. · Answer

Tinley was always cool. I learned how to shoot a bow at Freddie Bear Archery when I was a kid. I did property claims there for almost 10 years and it seemed once you got into Will County the risk profile improved dramatically and you got out of Cook County property taxes. How's Crown Point these days? Yeah it's Indiana but it's the Chicago suburb of Indiana. I had a lot of fun doing business in Chicago while owning all my property in 3% property tax Indiana.

There was a time I was buying houses in Mishawaka, Indiana for 5-10k a piece. That's a small city right next to Notre Dame University that no one paid attention to. Little gold mine for land lording for a short time. I bought this 3 unit property there for $24,000 back in 2006. Total steal: https://www.zillow.com/homedetails/808-N-Main-St-Mishawaka-I... Those interior photos bring back memories. They haven't updated this much at all from what I did to it.

Ignore anyone who makes jokes about Indiana. You can make some solid cashflow there.

Sean McKee · Answer

Thanks for sharing this information. This is very helpful. I'm finding my search radius expanding due to limited inventory.

Aaron Zimmerman · Answer

Thanks for sharing! I do some private lending to active investors/flippers in that general area (I know it's a big area) so I appreciate your insights!

Where the cash flow actually is in the Chicago south suburbs right now

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