I always enjoy reading about the thought processes that people have when deciding what flights to take for any given trip. I understand that some people don’t enjoy reading about that (especially when we are talking about “boring” economy travel), so if that’s you, hopefully you didn’t click through to read this post, as I fear you may be sadly disappointed. Thankfully, I think that we are truly living in the golden age of travel, with free cancellations on many airlines. On the one hand, it’s nice to be able to book multiple options and cancel closer to the date of travel when you know your schedule better (or if better options don’t arise). On the other hand, for me at least, it lends itself to analysis paralysis, where I can’t seem to make myself book something until I KNOW that’s what I want to do (even if it’s totally cancelable)
A Trip To Boston With Many Options
All of that is the backdrop to my story of a trip from my home in Cincinnati to Boston. I have been using PointsYeah to monitor the cost of flights periodically, and I’m at a spot where I’d really like to lock in a routing. Here are a few options
Nonstop On Delta
My preference would be to fly nonstop on Delta. Delta currently flies CVG-BOS three times daily. The early morning flight and the evening flight are both available through Delta’s partner Virgin Atlantic at a very reasonable 11,000 miles (it would be 8,000 to transfer from American Express Membership Rewards but I already have Virgin Atlantic points in my account)
However, the midday flight, which is the one I would PREFER to take, it not available through Virgin Atlantic – instead you can only book that with Delta’s own miles, for over twice the cost.
This is despite the fact that all three flights are listed for the same cash cost.
One Stop with United or American
So I’m not paying 27,000 miles, and until or unless I can talk myself into the 6am or 6pm flight, I’m left exploring a connecting flight. United has a flight that is decent timing. The only downside of that is that I’d have to transfer to Lifemiles which means a) my miles would be orphaned over there, b) There’s a $25 partner booking fee.
Another option is flying American with a stop in Philadelphia. This is available with AA miles
as well as Alaska miles
The problem is that I am running low on both Alaska and American miles, mostly because I’m finding so many dang good deals using them!
(SEE ALSO: Is American AAdvantage the best loyalty program for domestic flights? (I think it is))
This is yet another amazing AAdvantage redemption – clocking in at 4.11 cents per mile.
The Bottom Line – What Would You Do?
Currently I have the AAdvantage flight booked, though I may transfer to the Lifemiles / United one later. And of course, if I see availability on the nonstop midday flight on Delta / Virgin Atlantic, I will definitely book that one. But I’m curious – what would you do in this situation?
What flight would you book? Leave your thoughts in the comments below
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Dan Miller travels with his wife and 6 (SIX!) children. He loves to help families travel for free / cheap, especially larger families. If you are looking for help, drop him an email at 
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