Airbnb in Chicago

[Trevor Fritz]

Hi everyone, 

As I navigate my way through finding a second property to buy, I am considering buying a primary residence in the Chicago area, near I90 between Irving Park and Wicker Park. I work in the suburbs and spend a considerable amount of time staying out there due to work obligations and coaching.  Ideally I would find a 2 bedroom and rent out either 1 of the bedrooms at all times or rent out the entire unit for an additional cost when I am not staying in the city.  I am closely following the city ordinances that loom on the horizon regarding airbnb as well.

The questions I have are:

What is the typical demand you have seen? (posted for all 7 days, how many do you get rented out?)

What may I have to provide these short term tenants? 

Any headaches or positive stories you have had?

Thanks for the help and I look forward to hearing back and learning from you all!

[Jonathan Klemm]

@Trevor Fritz - Happy to connect and talk AirBnB.  I've actually tried it once before and then most recently started up again.

I leaned into AirBnB because at the beginning of COVID many AirBnB ended up folding up shop due to the long time with no traveling.  Now the market is much less saturated.

I make sure to provide an awesome space that people will love and want to come back to.  Take the time to do things other people won't and you'll have great success.  My vacancy is at about 70% currently which is great for this time of year.