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.

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.

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

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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