Lease dates - Chicago

[Kavan Kucko]

Hi all,

I purchased a 2 unit rental property late last year that was already fully leased. At least one of the units plans on re-signing. Their lease is up at the end of September. I'm happy to have them re-sign but my question is: should I set the lease end date of their next lease so it lines up in a better month than October for future tenants? Do people have a sense if it is easier to fill vacancies in Chicago in May/June thank say Sept/Oct? I know more people move in May/June, but I bet there are also more units that need to be filled around then, so maybe its a wash?

I am considering writing something like a 9 month lease, letting them know they'll have a chance to re-sign then but just setting up a better vacancy timing should they not want to re-sign next year. Does anyone have experience writing leases for something other that 12 months? 

Thanks,
Kavan