Short-Term Tenants...Not So Short-Term

[Bradley Levy]

Hello All,

I'm hoping for some advice.  My partner and I purchased a Chicago two-flat back in December that we owner occupy.  It took us 1.5 months to rent our other unit at a price lower than we wanted.  I attribute this to the lull in the rental market in the dead of a Chicago winter.  As a result, we took on a "short term" tenant that had a 3 month lease with a month to month extension while their house is being rebuilt (had fire).  We are now heading into our 9th month and are quickly exiting what I understand to be prime season for renting in Chicago.  I'm torn because I don't want to kick these people out but I don't want to screw myself where they up and leave me in December.  The logical answer is terminate the lease and the emotional answer is to let them stay.  I'm  wondering if I can find some common ground here.  Can anyone speak to when the Chicago market takes a dump for the season?  I appreciate any opinions, input, or anecdotes of similar situations.