Other North & South America Frequent Flyer Programs - Porter to MDW then on to PIT with WN -- Connection time?

I have a porter flight leaving YTZ at 3:00 and supposedly arriving in MDW at 3:50 (1hr50min flight with the time change, which seems fairly long). Would I be able to make a 4:40 flight to PIT on WN? I have no bags checked, but I will have to go through CBP in MDW (YTZ has no preclearence). Does anyone have any experience clearing customs in MDW, and is it possible to return airside without having to use the normal security lines (i.e. can I use special lines specifically for connecting pax or do I have to go through the normal airport lines)?