That is a really great idea. I didn't think about that at all, in part because I'm not too familiar with the transit rules. As long as it is acceptable to transit via ORD after leaving the U.S., that sounds like a significant improvement.

Thanks as well to Viajero about the LAX-SJO tip. I am planning to have all of the segments dated, but we'll see how that goes when I actually go to reserve it in a few days.