I searched for this and couldn't find anything- but I'm not even sure what I'm searching for. Are there any threads on the best way to travel on UA with someone flying out of a different city? My girlfriend and I have been spending 4-5 days in Central America every couple of months- she departs from BWI/IAD, and I typically fly out of DTW/ORD. She has no status on United, and I have roughly one billion miles to spend.

It seems like every way I book a trip is the dumbest way. If I try to fly to IAD on a separate ticket first? Delayed flight, no delay protection due to different PNR. Try to meet at the connecting point? No club access for her (been using CC passes but running low), have to call to move to E+ on shared flights. If we have to return to a different airport than we started, it gets even more confusing on what I can and can't do with UA.

I can't imagine I'm the first person to run into this issue, but I also don't know if its "solvable".