Which Airline?
 

So we already have the chase sapphire and love it, however due to the fact I took a huge pay cut when I changed jobs and my wife needs $3000 in dental work, I was thinking of getting another card. We actually have plenty to choose from in our house already BUT we are going on a cruise next year from DBX to FCO and we were thinking of getting a UAL or AA card since we would be flying in and out of ORD most likely.

Are either of these better than the other? We had a US Airways card and trying to use the miles was like pulling teeth so we no longer have that one. Are these 2 similar, is it hard to use the miles? If so any suggestions would be welcome!

Which Airline?
 

If you had status with US it would be very easy to use miles. Same goes for any other airline.
Having just tons of miles is not that easy to redeem the miles shortly before the flights. Plan at least 6 months ahead. It will be easier to use your miles from most airlines.

Which Airline?
 

What do you want from the UAL card, free bags? Chase Sapphire gets the same points for the same fee doesn't it?

The 100k AA executive card requires $10k in spend in 3 months. $3,000 takes a nice chunk out of that. It's a $450 AF but $200 in rebate on first $200 in charges, and comes with Admirals Club membership.

Thanks for the suggestions, mostly just looking to see what would be best for airfare, don't really care if I have to pay for bags. Its the booking 6 months out that gets me, I'm lucky if I know a month ahead what my schedule will be.