Hey all — just wanted to share some quick thoughts from my experience running a short-term rental here in Chicago and why I think more people should be paying attention to the Midwest.

I’ve been house hacking a 2BR in-law unit in Portage Park (NW side, not touristy) for the past 2.5 years. It pulls in about $32k a year, covers most of my mortgage, and has been a great way to build wealth without having to go full “Airbnb mogul.” I also manage some Luxury ground up builds in Colorado, but this is my 'live for free' strategy.

Here’s why I think this kind of setup works really well here:

1. Chicago’s tough rules actually work in your favor
Chicago's short-term rental rules are strict — licenses, insurance, 2-night minimum, ect. Most important: in most cases it needs to be your primary residence (unless its in a larger building with less than 25% currently as airbnbs AND legal in the HOA). That knocks out a ton of out-of-town investors

A lot of hosts fake the “primary requirement” thing, but they’re technically breaking the rules. Since I actually live here and rent out the lower unit (which isnt technically another 'unit', I’m 100% compliant — and I’m not competing with a flood of illegal or high-volume operators. Way less saturation if you do it by the book. I will say it looks highly lucrative for the investors renting out 5/6BR homes with solid amenities, although legally dubious and not possible to launch multiple listings. 

2. Midwest pricing still makes sense
Compared to places like Florida, Texas, or Tennessee — where inventory is surging and it’s turning into a buyers market — Chicago’s still solid. Inventory is super low here, which is keeping upward pressure on prices. Reventure.app is forecasting about 5% appreciation in 2025, and we’re still in seller’s market territory. That stability gives me confidence in the long-term value of the property.

Plus, entry prices here are still reasonable, and the rental demand is strong enough that the numbers actually pencil out. That mix is getting harder to find.

3. There’s demand, even outside the “hot zones”
I’m not in downtown or a trendy area, but I still stay booked. I get tourists, business travelers, folks visiting family or coming in for events. It’s steady. Summers are obviously busier, but winter doesn’t completely die — I’ve learned how to price and plan for the seasonality.

If you’re thinking about getting into STRs and like the idea of house hacking or finding something low-key that still cash flows, I think Chicago (and the Midwest in general) deserves a look. I’m a local realtor alongside a property manage and help people find these kinds of setups — happy to connect if you’re looking into it.

Anyone else running STRs in less obvious markets? Would love to hear what’s working for you.