How to House Hack in Chicago with 150k

[Christopher Petsko]

Hi everyone,

My partner and I live in Durham, NC, but we have a strong attachment to Chicago, IL. I did my Ph.D. up at Northwestern, and I fell in love with the northern neighborhoods (Rogers Park, Edgewater, Andersonville).

Long term, he and I want to own a place in Chicago. The goal would be to acquire an investment property that we can rent out when we’re not in Chicago, but that we can use for ourselves whenever we’re there (e.g., for the summers, parts of the fall and spring).

We have 150k of investible capital, but we’re at a loss as to how to invest it. Initially, we thought we’d buy a condo in Rogers Park and then list it on AirBnB when we weren’t there, but it looks like AirBnb laws make this strategy complicated. Another thought was that perhaps we could try to move forward with a multi-family unit and rent out all but one of those units—but 150k doesn’t seem like enough capital to move forward with a multi-family unit. (We can handle some cash loss per month, but not a ton; ideally, we’d like to do something that results in cash flow.)

Any advice that this group has for us would be deeply appreciated. I’d also love to work with an agent, if anyone has good recommendations.

Thanks in advance for your help,

Chris