Short term rentals in downtown Chicago?

4 Replies

I have been researching the topic of short term rentals in downtown Chicago and would like to find out if anyone has any hands on experience with this and can provide some additional insight.

Target audience would be vacation and corporate rentals.

Marketing is pretty well covered by sites like AirBnB, VRBO, etc and currently posted properties have their calendars filled at approximately 50-80% rate. 

It looks to me like it makes sense financially but there are several risks that might turn it into a bad investment:

1.) Recent NY and SF legal issues for short term rentals (AirBnB specifically) and a possibility of the same happening in Chicago. - my research shows that it is legal to do it in Chicago at this point. License fees for that specific rental have even been established in the last few years.

2.) HOA issues - this will be case by case basis but even if it is allowed now it could change at any point. Not sure what can be done to alleviate this risk.

Anyone in this market already or looking to start? I would love to hear your thoughts.

Thank you in advance for any feedback.


My wife and I looked into this. You might find a property that works, but we gave up. Most condos have very strict limits on minimum rentals--mostly 60 days and up. We spoke to a few owners who had their vacation rental operations shut down by their condo association and/or the city. Several rental agents also told us their were local ordinances against short-term rentals as well. Good luck.


@Matt Kesner  Thank you for your advice.

The way I see it there are too many risks especially dealing with HOAs. The ones I checked so far did not allow short term rentals. 

If I already owned a condo it would be an interesting strategy to try but buying one for that specific purpose might be a little much especially since it would be hard to support it once converted to long term rental. 


Agreed. You may want to look at student housing. We were told by a couple of realtors that you can accomplish something similar by buying condos near the schools and renting them to students. Apparently the rent is higher, (so is the wear and tear), and they are often empty during summers so you can use them yourself. Let me kno what you end up doing in Chicago. We love the town but live on the west coast. We would like to find a way to invest and spend some time there every year.

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