We have pretty negligible miles on AA (separate accounts), Delta (separate accounts) & Capital One.

Sara AA - 13,620
Mikey AA - 42,251
Sara Skymiles - 11,992
Mikey Skymiles - 15,703
Capital One - 11,036

Truth be told we take only 1 big trip a year and then smaller US based trips throughout. We definitely don't plan in advance or use our points well. We don't even use or credit cards well.

Anyhow, I realize it makes more sense to pay both ways but try explaining that to my husband. He just wants to spend as little actual money as possible.

These are the dates we are thinking about July 16 - July 30 2018

July 16 : NYC - FCO (fine with JFK,LGA & EWR)

July 30: MXP - NYC (fine with JFK,LGA & EWR)