hmm... This is very tempting.

1) Does anyone know if you can have overlapping R/T's? Example: I buy BOS-ORD-BOS, leaving early some Sat morning, and returning some late that night. But I also buy a ORD-PIT-ORD (or whatever the cheapest fare from ORD is) for Sat mid-day. Is there any reason why such a thing wouldn't work? Or would they see that as trying to circumvent their non-stop rule?

I'm just trying to figure out cheap ways to do this from BOS without having to spend the night, and the same-day BOS-ORD fares are about $200, making it not worth a MR. Unless someone in BOS has found a way to make this work?