Questions and Answers

I am planning a 2-1/2 week trip with my wife to Hawaii in Nov 2017 (It could start in late October, but returning before Thanksgiving).

I have a very substantial number of Ultimate Rewards points, and ~100,000 Membership Rewards points, and I am looking for the best and most efficient method for redeeming these for airfare from Columbus OH to/from Hawaii and a couple inter-island flights. I am pretty open on days of the week for travel for the flights between mainland and Hawaii.

Initial thought is to try to book Business/First class through SkyPass on partner Delta, and transfer UR points to SkyPass to cover the flights to/from mainland. If possible, I would like to do stopover in HNL for one night before continuing to Hilo. Then do open jaw with return flight from OGG to CMH. Does this make sense, and is there any real possibility of getting this?

For inter-island flights I was considering booking through Virgin America and transferring MR Points to cover these fights. Does this make sense (and is it a likely possibility), or are there better options?

This is my first time trying to use awards for a major vacation like this, so I may be totally clueless. Any help is appreciated.

I have no experience with booking inter-island flights so I can’t help you there, but last fall my wife and I flew roundtrip from CMH-OGG.

Skypass is certainly worth looking at. In addition, check out FlyingBlue which usually has decent award rates on Delta flights and occasionally has great promo rates (but not often out of CMH unfortunately).

We booked two economy roundtrip tickets on United for 45,000 points each, which was a decent value considering the tickets would have cost roughly $1250 each on all major airlines. We transferred in Denver on the way to Maui and in Chicago on the way back.

Delta may be different than United but one thing to keep in mind is that airlines often use older planes to fly to Hawaii. Our flight from Denver to Maui was a 757 that looked like it was about 20-30 years old. It only had overhead screens which didn’t work at all the entire flight, and no wifi. The first class seats were angled and looked really old/worn. I would have been pissed if I paid or used miles for a first class ticket on that flight.

On the way back (OGG-ORD) we flew a 777 which was much newer and nicer looking. There is always the chance of an equipment change but before you book make sure to check out the type of aircraft you would be flying.

Have a great trip!