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Request for help/guidance with using points for flights for HI trip 2018

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This is my first request for help, so please be kind with responses if I have omitted any details or posted incorrectly. I am looking to travel to Honolulu, HI on 3/24/18, and catch a flight back on 3/31/18. I'm trying to plan far in advance so that when options open, I can pounce on them. Departure airport would be either CAK or CLE. The trip will be for myself and my 9 year old. I am familiar with how to utilize options when it comes to deals for hotels, and I have done quite a bit of searching when it comes to utilizing points for flights, but I am still a little clueless for maximizing points for flights. The hotel portion of my stay is all set, but l would be grateful for help/direction for the flight portion.

I have searched FlyerTalk and this site for guidance. It looks like Korean Air's Skypass is the best option. Due to a back problem, I really, really want a lay-flat first class option for the longer leg of the flight, and I would therefore need to book the same for my child. If need be, I can just do first class for the return trip, but that's not my preference. Although flights for my time frame aren't yet published, for the past couple months I've monitored what's available for this coming March, as well as next January (the latest option currently available) to get an idea of what my flight options will be. It looks like I would need to leave early on 3/24, and fly a red eye on 3/31. To avoid first flying east on the initial departure from Ohio and adding extra hours to travel time, it looks like Delta out of ATL is the best option. To book directly through Delta using points it exceeds what I have available to transfer. That's why I was going to utilize Skypass because I read that the points needed to book a Delta flight through them are far less, but the bulk of my points are in AmEx points, and I don't see Skypass listed as an option with them. Here's what I have available:
220,000 AmEx points
68,000 Chase points
137,000 Citibank points (with Premier card, can transfer to a few different options)
60,000 Starwood points
195,000 Marriott points (I realize I can combine the latter two, but I haven't yet)

If at all possible, I'd prefer to book airfare using just points. I have no problem paying cash for the economy flight to and from somewhere like ATL though, and I have no problem paying for some fees with cash as long as they aren't ridiculously high. Travel dates are not flexible. As long as the seats lay flat I'm open to other airlines and layover options, but I wouldn't want more than one layover. Thank you in advance for suggestions and guidance.

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rated:
I'm certain I'm *not* the individual best suited to answer your question (I have no experience with Skypass), but thought I'd offer the following from my relatively limited perspective:

- AmEx points reportedly transfer to Marriott Rewards points (via Starwood) at nearly a 1:1 ratio (http://millionmilesecrets.com/2016/10/11/transfer-amex-membership-rewards-points-to-marriott/ )

 - Starwood points transfer to Marriott Rewards points at 1:3 ratio.

- Marriott offers a 20% discount when redeeming for United MileagePlus miles via their RewardsPlus program (http://www.marriott.com/rewards/usepoints/morerew.mi )

- United reportedly offers non-stop flights between HNL and ORD / Chicago (http://nonstopfrom.com/honolulu-hnl/ ), so I assume potentially one-stop via either CAK or CLE.  (Not sure if this is available everyday of the week.)

- Looks like 90,000 MileagePlus miles for a first class ticket. Not sure about lie-flat seating on those flights.

Hope this may help in your considerations. 

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Thank you pokeineye. I did look at seat options and saw United has lay flat seats with United, from DC or Chicago to Honolulu. It is 180,000 points roundtrip for each person which is a possibility, but 360,000 miles just seems so steep. Good to see that there are so many lay flat options though.

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I know you mentioned using points for this trip, but I live in NEO as well and thought it would be worth suggesting you search flights out of YYZ (Canada). Yes you need a passport and there is a little driving, but flights to Hawaii are a lot cheaper, like half the price.

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Thanks rockets00. If they had non stops out of YYZ it would definitely be worth the drive, but it doesn't look like they do. Also, $6,200 for 2 first class tickets if I pay cash is out of my budget. Thanks for the tip- will include YYZ in my searches for future flights.

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You can transfer amex, chase, starwood or citi(I would transfer citi as they are a bit less universal) points to Singapore airlines and then book first on United to HI for 30k one way. Comes to 120k miles for two roundtrip tickets.

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Sausuma- That would be amazing!! Thank you so much for the info.

I've spent some time today looking at Hawaiian Air, United and Delta options. Hawaiian goes out of JFK, but it's almost impossible to get a non-stop from my area to JFK, and I'd like to minimize any other transfers and additional layovers. Thanks to Pokeineye's tips I've seen that there are lots of lay flat options out of Chicago on United, so combining with Sausuma's advice this will be my current angle. Can't book until March options open though.

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I suggest you find the right dates on Flying blue for 30K one way in business and then transfer points to flying blue (KLM/Air France).  You will be flying Delta business.  I know Delta has lie flat seats from JFK, ATL to LAX.  I don't know about HNL.  I do know they have direct flights to HNL from east coast hubs (ATL, JFK, maybe DTW?).  I don't know if they are lie flat though.

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Fatxman- Thank you!! ATL to HNL via Delta had been my original focus. They do have lay flats, and they have a great option to ATL from CAK which is closest to me. It's great to have at least a couple options in case I can't get in with the top choice(s). This is exactly what I was hoping for, and I'm so appreciative for all of the advice. This will be a very special trip.

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@fatxman, Korean Skypass charges just 45k RT for Business class for the same seats Flying Blue rates at 30k miles each way on Delta Airlines. Better to go with Korean if can find availability and given their amazing change/cancellation policies.

My second option for best way to reach Hawaii on points would be Singapore Krisflyer for flights on United Airlines if cant find desirable availability on Korean Skypass.

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Cool- thanks njdealguy. I did some searching yesterday for mock trips in Oct through Jan, leaving on Saturdays. Tried on Skypass and Krisflyer but got no hits. Tried out of CLE, CAK, ATL, JFK, and ORD. Threw in a couple of Tuesdays in January (the latest one can currently book) just for good measure, but still no business or first class matches. Am I missing something? When I try on United or Delta I do see matches, but their point requirements are much higher.

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Check Virgin Atlantic which can be transferred from AMEX MR at 1:1 ratio. US mainland - Hawaii round trip business class only needs 80,000 miles. Airline award tickets may have limited availability. Make sure it's available before transferring AMEX MR to miles since transfer is final.

Never transfer AMEX MR to Marriott. MR worth at least 1.3 cents/point while Marriot worth probably 0.5-0.6 cent/point. Transfer from Marriott to United is around 2.2-2.5 : 1.

Or the other option is to sell unwanted rewards/miles at broker milesp2p.com and then pay cash for economy class, which may end up with cash on hand to enjoy.

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Thank you fiustudentable- I will look at that option. Appreciate the insight.

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Also consider Alaska Air, converting Chase URs to BA Avios (believe it should also be possible to convert AMEX MRs to Avios). As Avios redemption are based on distance, with decent availability on Alaska - who now happens to have the most flights from the mainland US to Hawaii - your points will go a long way. This assumes you are willing to fly in economy; deals on first class award seats to Hawaii are pretty much unicorns these days, regardless of the carrier, best advice is to find discounted cash first - starts at about $500 each way on Alaska. US carriers have all but eliminated widebody aircraft with lie flat seats in first, those remaining sell at a significant premium - cash or awards.

One of the challenges booking Alaska awards with Avios is finding award availability, as it cannot be searched on the BA website. Best to use a search tool like Expert Flyer for W awards, from Alaska gateways with connecting service CLE - SEA or PDX? Best availability will be Tues-Wed-Sat, so be as flexible as possible with travel dates. From experience, when you call BA to book, provide them with specific flights and dates of travel, may be necessary to call a few times to find someone who know what they are doing. BA should not charge a phone booking fee, as seats cannot be booked on their website. This may require positioning flights, overnight stay in either / both direction(s).

Another option is to sign up for the Alaska premium credit card (offered by B of A), which offers an annual companion pass ($100 plus taxes), good on all available flights - in economy. You can also earn bonus miles (believe it is on the order of 35k - 40k), which can be used for upgrades on paid tickets - including companion pass.

Finally, keep in mind that your Citi TY points are worth over $1700 in cash airline purchases, on ANY carrier. If you end up going this route, I would hold off until about 45 - 60 days prior to departure to purchase the ticket, which should be the sweet spot in regard to price.

As someone who visits the Hawaiian islands several times a year (using primarily Alaska nonstops from SAN for the past several years), I question if Hawaii is worth the time and grief for anyone east of the Rockies. There are PLENTY of equally great destinations in the Caribbean, Mexico and even Central America that are more accessible, lower in cost from the East Coast and Midwest.

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Shank, thank you for all of the tips. Well that just doesn't sound right...

I will consider Mexico for the future, but HI is just easier, and I feel safer to navigate given our dynamics. I have a free week in a 2 bedroom accommodation at a gorgeous resort, and my son really wants to go so I'm making it happen. It looks like I'll be checking for availability in a couple months, and it's good to know that 2 months out might actually be the time to book the flights. At least I won't panic if I can't find anything right away. If I can't get first class then maybe I'll look into purchasing 3 economy seats together so that my son and I can lie down on the red eye. I can't sleep sitting up, and then I'm a mess when I finally land.

Excited to try out all the great advice I received. Will report back once I make a selection, and if anyone else has anything to add I'll keep watching.

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So... I've been playing around with dates to see what availability is like at 6 months out, 10 months out, etc. I anticipate that flights for my actual dates will become available within the next one to four weeks. It does look like there are a lot more options for 8 months out, so I'll see if that holds true over the next few months. Delta has an amazing first class option for CAK to ATL to HNL and back- perfect times, only one layover each way, and lay flat seats for the bulk of the trip. It's important to me to have an option like that at least for the return trip, so I'm considering using up my AmEx points to transfer to Delta and book it at 117,000 points per one way ticket x 2 for the return trip. Based on comments received, options shown when looking at availability for the recommend frequent flyer programs, and also on feedback from a Korean Air rep, it seems like this may be my only option. For the trip out though, I can suck it up and fly economy. I will be in serious pain for days if I have to sit through a red eye on the return trip though, as there is no way I can sleep sitting up. I tried it once 9 years ago and will never do it again.

Two questions- it's my understanding that I can book an award trip through Korean Air, and if I need to cancel it I incur no fees or penalty. Is that correct? I don't see that one way trips are an option using rewards on Korean Air, so if I paid 25,000 points per ticket x 2 to fly out on an economy flight but then flew back on a Delta first class flight that I booked through Delta's frequent flyer program, would there be any problems? If it would help, I could always contact Korean Air prior to the return date and just tell them I needed to cancel my reward return booking? I realize the 25,000 points per ticket would be gone, but I didn't know if there was any penalty for not completing the booked flight.

As always, thanks for the help.

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Addition: Just realized that I can book the one way ATL to HNL economy flight on Flying Blue for 15,000 per ticket, and lots of Saturday availability, so that will cover the option to get to HNL. If only I could reduce the return point cost.....

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Skim1 said:   Well that just doesn't sound right...


 

What does not sound right?

I sincerely hope you enjoy the trip, but I simply do not consider Oahu worth the more than 11 hours of travel in each direction to get there (9.5 hrs ATL-HNL, 1.5 hrs CAK-ATL, plus layover) - not to mention the excessive number of miles. Shank out, drop mic.

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