Aaron I'll just chime in here a bit late. IMO you won't find an easier large airport to transit than Schiphol. When living in Holland for a few years 5/6 years ago was in and out of there 2/3 times per week. Everyone at the airport (the whole country, really) speaks perfect English, they have lots of 'people movers' to get you from gate to gate, area to area, and it is very well signed in Dutch and English. You will not need to speak Dutch and two hours one way and 85 minutes the other will give you lots of time to make your connection.
Chicago to Schiphol should pose no problems; the other leg, to/from Rome should be OK so long as weather (read, fog) doesn't interfere. Spring and fall on inter-Europe flights are often delayed because of fog/bad weather. I've spent a few extra nites in Zurich, Vienna, Munich, Paris, Rome, Sarajevo, etc., because of the weather (spring/fall) and flights not being able to go anywhere. They can almost always get into/out of Schiphol because of the airport's avionics, not the same for the cities where the flight are headed to/returning from. If you get stuck in Holland, doesnt' get better than that. BTW, was stuck at O'Hare one night because of weather -better off at Schiphol.