Thanks for the info. I'll try calling UA again. As for no Complimentary Upgrades for Gold, is that b/c of ORD? I've been getting my upgrades from DTW-iAH and IAH to wherever, about 90 percent of the time. Granted, I usually book pretty late (within a week of my departure) and always travel solo. But I avoid ORD like the plague.

I'll check with UA again about the baggage and the UG. As stated, I got 2 separate replies on 2 different dates. 1st flight is ERJ and no big deal, but I would appreciate an UG on the 738 and on both return flights.

Basically I am getting that if I split off from my son, he loses his free checked bags. Why does it have to be so confusing?

That said, thanks so much for the help. I knew I wasn't the only one confused. I don't expect an UG on Friday's flight as it is already showing only 3 seats from ORD to MCO and that is fine. The return flight, though, is important as I'll be wanting some peace.

Oy, solo trips are so much easier!