A friend of mine asked me this question... and I bring it to Milepoint for expert advice. The family (4 of us) are going to Europe next summer. I need to go from ORD to Athens Greece we will board a cruise and end up in Rome so then I need FCO - ORD Most of the flights from ORD to Athens stop in London. I wouldn't mind spend a couple of nights there before I head to Athens. but I am thinking that will add a lot of cost. Am I best off booking everything with 1 airline as multi-city or trying to piece together 1 way tickets. It seems to me one way tickets to and from Europe are very expensive but within Europe they are very cheap. The stop over in London seems problematic Obviously I have plenty of time but not sure when to book this. Obviously on the flights over to Europe I want to make sure I have good seats as we will unfortunately need to fly Economy. I have low level status on AA and UA. I know this is a lot and somewhat complicated but I would appreciate any direction you could offer.