STR in Windsor Park, Chicago?

Question

I’m in Chicago visiting my daughter, who lives in Windsor Park. There’s only one hotel nearby, and every time I go it’s full of families/parents visiting their college kids. When I looked for an Airbnb there weren’t many close by or in a good location. It’s got me wondering if it’s a good area for STR and why there aren’t any. The area I’m looking at is walking distance to the subway (blue line), near restaurants, etc. no parking but the apartment would have one space. I had thought of purchasing an apartment for a long term rental, but wondering how to determine if an STR would work better.

Shannon Ilas · Answer

@Jonathan Klemm, thanks. There are a few in Wicker Park, but not the area I was looking at specifically.

It’s more residential but walking distance to the shops/restaurants on Division.

Jonathan Klemm · Answer

@Shannon Ilas - I have an AirBnB in chicago right near wicker park and it does great.

I've always taken the approach of providing a great product in a good location (close to blue line and highway as you mentioned).  I wouldn't say there are not any airbnbs in this area though.

Check out the website AirDNA for Airbnb data.

Crystal Smith · Answer

An STR will work in Wicker Park.

Shannon Ilas · Answer

@Crystal Smith

Good grief, I meant Wicker Park! I have no idea how to change the title of my post.

Crystal Smith · Answer

I assume you mean Windsor Park down on the South Side.  Chicago's a good market for AirBnB but it's all about location, location, location. The location has to be near entertainment, tourist attractions or Universities.  If you're talking Windsor Park on the South Side in my  opinion the probability for an STR success there is low because it doesn't meet  any of those criteria.

Gerald Pitts · Answer

I stayed in a great Airbnb on lake Michigan in Rogers park recently.  However, I prefer vacation rental markets to Metro markets because STR laws aren't as likely to change.

in a Metro market, I would think you would want to have a backup exit strategy of renting it as a long-term rental.  And I've heard tenant rights in Chicago are superior to landlord rights. Just make sure and do your research.

Shannon Ilas · Answer

I’ve checked and it looks like they aren’t prohibited. There are a few closer to Division St, which is where the metro station and restaurants are. I could see that appealing to a certain crowd, but families may want to be more residential (quiet) or near a park but still walking distance to the other amenities. I live in suburbia myself, so maybe I underestimate the allure of being in the middle of it all. The building I was looking at does have an HOA so it may be that this particular one won’t work. I’m curious how much activity Airbnb does when it starts to snow in an area like Chicago?

John Underwood · Answer

This makes me think STR'S may not be allowed in this area, but if they are, I would be looking into the numbers on buying one here.