Not a Guy, but knowledgeable about the area you speak of;
Hey Jaime, a few things to consider with your search.
Since my Incall is on the north side I will offer suggestions based on my experiences. I am not south loop and have nothing to contribute on that end sorry.
I'm within five minutes of many Kennedy stops like Belmont, Addison & Irving Park at the merge. They are also all blue line accessible from downtown and O'hare which is very helpful.
I considered being near the above locations plus watching for meter and permit parking of which my Incall has neither. I am fortunate to have found a place with no meter parking and is also non-permit as there aren't too many places like that near expressways and trains anymore.
Parking by me is typically only an issue, once per month on street cleaning days during those hours.
Meter parking gets inconvenient and expensive. Permit parking is way difficult to deal with.
You will need to make trips to these areas OR ask these questions if they are deal-breakers before even going to look at a potential location. I can be downtown in as little as 10-15 minutes during non rush hour traffic times. That all changes as every Chicagoan knows during high peak travel times.
One other thing to consider the Edens 94 expressway is almost always much quicker than 90 Kennedy!
You should be looking for a larger type multi property building on a quiet street without permit parking requirements or meters. I have found several affordable places in my few years in the business.
Good luck with your search. Reach out if I can help further.
Carly
-- Modified on 4/27/2014 12:54:33 PM