Need Help with Miles

Need Help with Miles
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My SO and I are planning a trip to Italy from Los Angeles in April. Between the two of us, we have points with American Express, Delta Sky miles, Citi ThankYou points and a handful of others. Trying to research the best way to utilize them to get the most bang for our buck has been migraine educing. Can anyone recommend a path forward? Thanks in advance.


Hi, grodinj, and welcome to the community! I feel your pain. Trying to figure out the best way to use points and miles can be maddening.

Many experts recommend starting such searches nine months to a year in advance, since that’s when you’ll get the most availability and the best deals. That doesn’t do you much good now, of course. At this point, I might focus on finding the best route that you can cover with your available rewards, rather than trying to wring out every last penny that you can.

As a fellow Angeleno, I do have one tip: look for flights originating on the East Coast as well as those starting in Los Angeles. Sometimes you get better deals on shorter international flights. We’ve cobbled together some nice trips that included a weekend stopover in New York, for example. It also breaks up what is otherwise a very long flight.

I’ll also check with our travel experts to see if they have additional ideas.


Hi grodinj! Thanks for your question. I agree with you that the whole points & miles space can be migraine educing - and I work in it every day for a living!

So the good news is that your American Express Membership Rewards points will transfer to SkyMiles at a 1:1 ratio. And through Delta’s extended network in SkyTeam, you may have more opportunities to see Italy. Start by searching the Delta website ( to get an idea of how much an award might be, and if your combined total of SkyMiles and American Express Membership rewards will get you to your desired destination.

Another option is to see if you can use your Citi ThankYou Points for a positioning flight to a major hub (like New York’s John F. Kennedy International Airport or Atlanta Hartsfield-Jackson International Airport) and then use the remaining SkyMiles to fly to Italy from there. The one thing to keep in mind is that if you do go that route, you would have to schedule plenty of time between the two flights because you will have to check in twice, and coming home you will have to clear Customs, which can take a significant amount of time.

Let me know if this helps, or if I can provide more clarity on your situation. Thanks again for sharing your question.


Joe gives great advice, and I’ll underline his recommendation about leaving plenty of time between flights to accommodate more than one check-in. I once booked us from Barcelona to Heathrow on one airline and then Heathrow to Los Angeles on another, and I will never, ever do that again. We had to fetch our luggage and go through customs TWICE–once at Heathrow and again at LAX. (Fortunately we had Global Entry to bypass the shockingly long customs lines at LAX…worth every penny.) Even if I’d left twice as much time, it would have been stressful. Using the same airline for both legs allows them to put your bags on the next flight without having to re-check them.