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!