Award flights BOS --> OGG
 

Looking for best strategy for 4 award seats in November. Initially wanted to do it in 1st class but can barely find 2 seats. Sitting on over 300k UR points but trying to use wisely so as to do other trips as well. Will be travelling w/ a 2yr old so with the time change, looking to spend 1 night in LAX or SAN on the way there, 7 nights in Maui, and then 2-4 nights in California on the way back. I have an itinerary on hold w/ KE Skypass for BOS-LAX, LAX-OGG, and then LAX-BOS, all on Delta, for 100k pts. KE can't find any availability OGG-LAX or I would be better off doing that and then paying cash for the LAX-BOS leg for $140/pp. Right now OGG-LAX is $314/pp, or I can do a 1 way flight on BA on AA metal for 50k avios. Does 150k pts total seem like a lot to be using for 4 in economy? Total cash price would've been $4,221.20 (in comparison, same trip w/ similar dates cost us $2,600 total for 3 ppl in Nov '16, baby was free then).

I have been looking for saver space on Delta, AA, United, Alaska, and Hawaiian using their sites and paid subscription to Expert Flyer. That OGG-LAX leg, for some reason Signapore KrisFlyer can't see saver space that I am seeing on United and Alsaka. Any suggestions on that leg instead of using 50k points for a 1 way flight? I even tried looking and found a saver flight from HNL to LAX, but Signapore couldn't see that neither (I would've then spent 6 nights on Maui, 2 nights on Oahu, and 1 less night in LAX). Thx!

Well, I have two pieces of advice. First, forget about spending a night in California on the way to Hawaii to help the 2 year-old adjust. They will adjust better than the adults will, so just GET there.

My other piece of advice is that saver awards to Hawaii are like a golden unicorn spewing rainbows. Either book a standard award or pay--it's not worth checking multiple times a day to try to secure single seats on various airlines, then stress about somehow merging all the reservations.

This is excellent advice. You can depart Boston and arrive Hawaii same afternoon. Jump in the Pacific and jet lag is gone. Wake up next morning and you are already there instead of waiting for the LAX shuttle.

If you find (non stop) saver space on AS, use your UR points to book it with BA for 12.5K per person one way (you have to call BA to do this).

As an update, I got the 3 DL flights ticketed thru KE yesterday. I found award space on Alaska for OGG to LAX. Called SQ who said they could see it as well. Transferred the points from Chase to my Krisflyer account and called back this morning. Well the next rep I spoke to stated she could see the flight and available award seats, but is only able to book Alaska flight numbers 1-999. And of course my desired flight is 1122. She went to check with a manager and came back with the same answer. I saw no data points on this previously. So now I have 48k miles with SQ and unable to move them back to Chase. Probably should've just went the BA/AA route even though it was a total 2,000 more miles. Search continues.

Just wanted to post my latest results. Long story short, don't give up. HUCA worked again. Again, had to emphasize looking for award space on Alaska, airline code AS. Took about a half hr on the phone and even her calling me back once but 48k miles for the 4 of us and $22.70, we are now ticketed. Total trip, 4 flights/segments for the 4 of us ended up at 148k miles and $67.5. Without stopovers in both directions, probably could've done it for just the 100k miles and $44.80 thru KE.