Hi again XS, I've looked at the aa site and as others have said the only valid connection PDX/ORD/GLA has you on the ground for hours at ORD. I wouldn't touch the connection you have as it seems to be two seperate ticketed itineraries, which would usually mean that if you do miss your connection then you'll be on your jack jones overnight. Even if you do have tickets with the same carrier it is becoming standard practice with a lot of carriers to not help you.
Would you consider two changes, perhaps with another carrier, so you either have more chance of making your connection/not sat around in o'hare for ages?