Chicago area short term rental investment

4 Replies

I have been searching for a 2 bedroom property on the northside of Chicago (Lincoln Park, Roscoe Village, Wicker Park, Bucktown, Lakeview, etc.) for a family member to occupy 1-2 months out of the year so that they can spend an extended period of time each year with my children. My hope is to rent out the property the remaining part of the year and turn this into my first REI property. The challenge has been with high HOA fees and taxes, as well as association bylaws related to short term rentals, even at best the cash flow each year would be minimal. With minimal cashflow I'm leaning towards just finding a short term rental for this person each year.

Is there anything I might be overlooking in a unique situation like this or suggestions anyone might be able to offer?  Thank you in advance.


Matt, I may be the most qualified to answer this, as 1) my niche is short term rental and 2) I was born, raised, and currently live and invest in the Chicago land area. 

I need clarity on what you actually need... but from the post it sounds like you may be targeting an area that doesn't fit your needs. Consider targeting an area further than Chicago,  but with an easy commute to the city. Oak Park and Forest Park would be ideal. My properties are a little further west

@Account Closed 100% on this. Those neighborhoods for lack of a better term are more strict and overbearing from my experience. That applies to rentals, condos, etc. Those are pretty much the most affluent areas in the entire city at this point (possibly short of River North although WP/Bucktown I think have been surpassing prices even there), so they're typically stricter unless you can afford a 3-flat or SFH.

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Thanks for that @Lucas Hammer .  Another alternative @Account Closed , I'm constantly keeping my ear to the street in terms of solid real estate deals in prime areas.

To help mitigate risk and cost, you may want to consider partnering up with someone on a multi-unit building and and split the profits.  I'm always looking to form strategic alliances with people if we can make it a mutually beneficial arrangement.  I have a approved $300k line of credit that is also pre-approved for an increase up to $10M.  So the opportunities are endless.

PM me and we can talk if you are interested.

@Lucas Hammer and @Dexter Crawford thanks to you both.  I suppose you're right.  Feedback from agents I know has been similar as well - those cash flowing own the building.  We're considering a long term play on the unit also.  My fear is getting away from the initial goal and jumping in to something that doesn't fit my criteria.  Thanks again.