The Award Booking Mistake I’m Not Making Again

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In the very near future, we head off on a much awaited return trip to Hawaii. Hawaii is a super interesting destination for many reasons, one of which is that even though for most of us is pretty far away spot, the majority of the planes that fly to Hawaii don’t have the fancy lie-flat seats that you would find if you were heading the opposite direction to Europe. However, from here in Houston it can easily take us longer to get to Hawaii than to many points in Europe.


The only nonstop option to Hawaii from here is a United operated flight to Honolulu, and even that is blocked at 8 1/2 hours of flying time. If you are going anywhere else on the islands and have to connect, it is obviously going to take even longer than 8.5 hours. By that point you could have landed in London, Paris, Amsterdam, etc.


Hawaii is still totally worth it once you get there, but I think the weird combination of pretty long distance flying without the decent availability of really “good” seats seems to make me do sort of stupid things. Well, there’s that and my husband’s self-imposed “rule” of not flying more than 4-5 hours if it isn’t in first class.

As I look at our upcoming itinerary to Hawaii I just keep shaking my head. We’re in first class. We’re going to Hawaii. We’re using miles at the saver level during spring break. That’s all awesome, amazing actually, but I still don’t think I did a very good job in getting us there.

My error was that I let the class of service be the driver of the decision making process and not the schedule. If the seats were truly amazing lie-flat seats that might be a tad more forgivable of a family travel sin, but on our outbound journey we are in normal domestic first class seats. Of course those are better than coach seats, but probably not really worth going much out of your way to enjoy…though again, Hawaii is kinda far so I understand why I did it.

Trying to absolve myself if this ‘sin’, this morning I texted my husband and presented a totally new option to get to Hawaii. The option presented cost fewer miles, only required two flights instead of our current three, would result in at least two more hours of sleep, but it was all in coach. He didn’t go for it.

The real issue here though isn’t that he was reluctant to totally change up our flight plans this close to departure, it was that I created this mess in the first place. While it is totally reasonable to take the type of plane and the class of service into account when selecting the best flights for your family, if you stray too far from simply securing the best overall schedule, you probably don’t come out ahead in the end.


Don’t fly too far just for a better seat and a meal

Never say never, but I very much plan to avoid making this mistake again. Obviously first class is more enjoyable than economy when flying as far as Hawaii, but simply getting where you want to be in as timely and logical of a manner as possible outranks the seat for me, especially if the first class seat you are chasing isn’t really all that hot anyway. I can guarantee at the point in our long journey when we could have been there if we just sucked it up and sat in economy, but instead still have a couple hours to go in our domestic first class seats, I will very much wish I ranked schedule ahead of seats. He probably will, too.

At the end of the day, we will still land in Hawaii for very little out of pocket cost, so I didn’t do too terribly in booking the trip, but I plan to do better in the future and firmly rank schedule over seats in the decision making process.

How do you balance the best schedule with the best seats when making your award bookings?

Keep the

Keep the focus firmly on the destination

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  1. Sitting 22 hours in SQ Suites SIN – FRA – JFK, when i could’ve done the trip much faster (my final destnation was Seattle), i realized that i might have been happier doing a quicker flight SIN – SEA in economy.

    Time is the ultimate luxury. Never again.

    • I suppose that depends on how you flew JFK-SEA (F or E). Personally, give me 22 hours SQ F and 6 hours UA F over any airline 17 hours E…anyday.

  2. We live on Maui and travel to California frequently to visit our kids who live near Sacramento. We fly nonstop on Alaska Ailines almost exclusively. Based on my experience, exit row seating has more space than first class. For me, space is more important than a meal and free drinks.

  3. I simply don’t care about class. Scheduling and a direct flight is preferable. Coach it is, then I pay the difference for Economy Plus.

  4. I’m flying from AUS to HNL in September, and AA from DFW to HNL offers lie-flat on their 767. Sure, the IFE is a tablet that mounts to the seat in front of you, but for an 8 hour flight + the 1 hour connection AUS-DFW, it was absolutely worth it. The alternatives were all AUS-LAX-NNL in domestic narrowbody first class recliners. The flight home departs HNL at 8:30pm and gets back at 6am, so a lie flat for a redeye like that is much better than any alternative that involves a layover in LAX in the middle of the flight.

  5. You’re in the same boat as I am and I also have the 5+ hour rule of it must be First/Business (although I’m willing to entertain Premium Economy). Also from where I live (near Kansas City) I would chose the better seat over saving a few hours every time. I’m tall and economy over 2 hours is torture. It’s like giving me the choice of sitting in the back seat of a Prius with two other adults or even children on a drive from Houston to Wichita with free bottle of water via Dallas OR…. sitting in the front of a Cadillac but routing to Wichita through Little Rock but you get free food and a cooler of beer for free. Guess what. I’m not much of a redneck but I’m going through Little Rock every time even if I end up drunk or hung over by the time I roll into Wichita 🙂

    Of course Maybe I’m tired after driving from San Antonio to KC yesterday 🙂 Thanks for sharing the post. I can’t wait to see your trip reports.

    • Totally agree. Maybe this should the TrumpBlog instead. Maybe I need to find another blog that helps real world families. I’m just joking MommyPoints. But don’t lose your loyal fan base by too many posts that there are rules that require first class.

  6. This is one of the most interesting posts I’ve read on Boarding Area. You bring up some of the same thoughts I’ve had relating to 1. when to insist on a first or business class seat, and 2. how does the flight schedule affect 1. It’s a much easier set of questions to answer if the flight is less than 4 hours in duration: domestic first class simply isn’t worth the upgrade cost. You mentioned the nonstop UA flight from IAH to HNL, but then state that to reach your destination, you’ll have to take three flights. I’m assuming those are inter-island flights? Here’s a though: I’ve tried UA’s new premium economy and I think it’s a good compromise: it’s got plenty of legroom, which is really what you want on a longer flight, and we already know that the rest of the first class experience on UA is kinda “meh,” so to me, that would be the correct compromise here. You don’t get all scrunched up in that premium economy seat, and you don’t overpay for a mediocre first experience. Hope this makes sense.

    • It’s a much easier set of questions to answer if the flight is less than 4 hours in duration: domestic first class simply isn’t worth the upgrade cost. ” Unless you are traveling to Orlando and there are a bunch of rowdy kids in flight. Then first class every time!

  7. Great article, and totally relateable for our family too! Last May we went to Maui and Kauai for our 25th anniversary, then went to Puerto Vallarta with the kids at Christmas. I’d say a solution to your class of air service dilemma is that Puerto Vallarta is just as nice but with better food, lots of local culture, just as luxurious, and only 2 hours from Houston. For us, the $26 cheeseburgers at the Fairmont Maui (using the two free Fairmont Visa nights) got old very quickly.

    • Same!! I was raised in Houston and always poo poo’d Cancun, Puerto Vallarta (sp?), Riviera Maya, etc. until we went to Maui followed by my first trip to Cancun (followed up by another). Omg Maui was nice but (and I can’t believe I’m even saying this) give me that 2 hr flight down to Mexico over Maui. I do miss the mountains but that’s it. Less hassle, MUCH better food, culture, etc. Even my kids prefer Cancun over Maui. I’m still shocked I’m saying this but it’s just so much better all around. No one is exhausted. No one cares about class bc it’s too short to care. Almost perfect.

      BUT I do know that feeling of just loving a place just bc you love it. Give me London all day everyday. No matter the circumstances (almost), idc I’ll at least want to go for it. I just love it.

  8. Tell me about it! I live on Hawai’i Island. I stopped using first class to fly back and forth to the mainland- it’s a waste of miles in my book because the product is so bad. The major airlines use some of their oldest metal for Hawaii routes. Guess they figure everyone wants to come to this destination so no need to impress. Alaska and Hawaiian first class are decent-ish. But still , they certainly don’t compare in ANY way to first class on EU routes. It IS a long and its crazy that not one flight has lie flat seats. My best gamble have been to travel at less popular times, play it nice with the TAs and FA and try to score a row to myself- It works sometimes. I don’t get lie-flat seating, more like side lie flat seating lol

    • @Cheri. I live in Kona on Hawaii Island too. I would love to connect sometime as I don’t know anybody into points and miles here. I’ve been doing it for more than 20 years. See my contact info below.

      I recently went to the Frequent Traveler University gathering in Seattle. I tried AlaskaAir premium seat on the way out and FC on the way back. I was really disappointed in FC. My seat was broken and didn’t recline. They didn’t serve pre- departure drinks although the plane sat on the runway for an hour due to delays in food truck arrival and then waiting for passengers from a delayed flight from Colorado! The plane landed in Kona at 2 AM (Pacific time) yet they didn’t have pillows or blankets on board. Food not good. While I’m not much of a drinker, I do recommend the Crater Lake Hazelnut and Espresso infused Vodka from a small company in Oregon, though you can get that in coach!

      @MP- If you would like help with any recommendations in Maui or a future trip to the Big Island or Kauai, I would be happy to help. I’ve lived here for almost thirty years. dar1ene at

  9. I made a similar mistake many years ago. My partner has the same rule…only fly economy if its 4 to 5 hrs flight…longer than that, he prefers business or first class. So I booked us a business class flight to Hawaii from New York. Much to my disappointment, the business class seats weren’t that much different from economy..ok, wider seats and reclines a little bit more…but I don’t think that was worth the extra added points.

  10. We flew from CDG-IAH-MCO because it was a better plane when I could have come up with better routings. Flying over our home airport and then having 2 hours of flight time, plus a 2 hour layover and then flying 2 hours back over the Gulf of Mexico to get home was when I first realized that I’d rather be home than in a better seat. That was 10 years ago and I still feel the same way. Every once in a while I forget and end up remembering while sipping my wine in a lie-flat seat when I’d just rather just be home already.

  11. I don’t know what airline you’re flying – that can be a deal-breaker – but I find it absolutely worthwhile to pay extra for first class to and from the Mainland. It’s not any one thing in particular, but added together, all the small things like preboarding, dedicated overhead space, extra legroom, wider seats, attentive service, free (and free-flowing) drinks, an actual meal, and mileage bonus make the flight that much more convenient and enjoyable. When I first started flying first, i did it for the “glamor” (if that’s still a thing), but after a while that wore off and I pick and choose what flights I feel flying in first is worthwhile. Anything over 3 hours or at night is better in First in my mind; day flights can go either way.

    All that being said, the carrier and aircraft also play a role. I would never pay to upgrade on the Hawaiian 767, but the A330 fleet is nice. Likewise I wouldn’t upgrade on the Delta domestic 767 but I do for the international 767 or Airbus. Alaska is a wash because first is usually only a little bit more expensive so the mileage bonus is worth it. If I can, I’ll also upgrade to lie-flat for overnights to Europe but I’m fine with economy or premium on the daylight return.

  12. One last comment – I would NEVER use mileage for first to or from Hawaii unless it’s pay with miles. The redemption rates are exorbitant. Usually I pay for economy or premium and use miles for the difference to first

  13. How do you balance schedule with class of travel, seats, when making bookings? It’s always most difficult when traveling with family and there are really no hard rules. Frequently you know it when you see it.

    We have 2 daughters and when we traveled with them when they were young it was frequently in coach. We would unusually book 3 in one bench and then 1 of us in another row, taking turns with the girls (which was usually preferred by us). MD80s 2+2 was a real bonus. Up front in F even better.

    If I lived in the middle USA going to Hawaii I would defiantly build in a west coast stay. Especially with little ones. Then the coach ride out and back is easy.

    FWIW Alaska really services the islands. We’ve been using the credit card coupons for 10 years now. My oldest loved those trips so much she ended up at U of Hawaii Monoa for undergrad.

    Enjoy your family trip to those magical islands.

  14. My wife and I flew from LAX-NBO (Nairobi) a few years ago. I was still relatively new to the miles game and only had Chase UR and AA miles; I didn’t know about AA to book EY, so the best I could do was transfer UR to UA and booked LAX-YYZ-ZRH-CAI-NBO in J. The return route was similar (4 flights). A couple of the products were nice, but still… 4 flights is a lot of transfers. Plus, we didn’t check in any luggage and carried everything in our backpacks. Even now, I wonder if paying cash for 2 flights in economy would’ve been easier

  15. I’ve flown enough now, both in business and economy on long-haul international itineraries, that I’m beginning to find where my line is for “worthwhile” mileage redemptions.

    Very high end business or first are worth it. I doubt I’ll EVER forget my flight in an Etihad First Apartment with my wife and friend. In fact, the Etihad business class lounge at JFK was frankly amazing. On the other hand, a Cathay Pacific regional business class flight is unlikely to be worthwhile, even if the seats are in the long-haul configuration (my oneWorld Emerald status gets me into the VERY worthwhile lounge in HKG, tho, even on an economy ticket!).

    Thanks for the thought-provoking post, Summer!

  16. I am petite so Economy works really well for me. Now if I could book an Apartment for every flight with my kids and husband, I would!

    I book my points redemption almost strictly based on value. I try to only redeem 12.5k per United flight to anywhere we fly in the US. I’ll move dates around, etc. I am flying my family of 4 from COS to MCO for 75k points during Spring Break. Infant is free and booked 3 R/T tickets at 25k each. Score! But – we will be in coach. It is a quick flight with a built in layover in Houston so we can stretch our legs at the Centurion lounge in the kids room.

  17. the last few years I have lived in DFW…we have found though we are a couple of hours closer than our old home in ATL we have less decent flights available from here to Hawaii…united is totally worthless…delta has lie down seats, but you have to go to ATL to get them so you add time to add comfort, and the skypesos cost is crazy, so they are no good from here….mergers took away other decent options, so we are left with AA. I usually work backwards, since the flight home is the overnight and comfy seats make sleeping easier. I have found 2 nonstop 8 hour flights that return from Maui, but after the merger extremely limited availability at business saver level (think 1 or 2 dates a year, either a year out or short notice) the other saver awards up front are run through Alaska air and require 2 stops so I don’t bother with them…the 2 non stops are usually 90k-125k business anytime. limited flights with seasonal discounts make the cost 67.5 which is what we usually wind up with….before the merger you had dozens of flights with good itineraries at decent award costs, so much for customer enhancement.
    Then the hard part is matching an outgoing flight to our return trip….we usually go for 2 weeks and do 2 islands, so flying into hnl or koa has a couple of options, though they seldom line up with return flights….my wife reluctantly agrees that if we can find a non stop 8 hour flight out we can do it in coach. We are usually awake and excited to be going to Hawaii so the seat isn’t used for sleeping much…we have tablets, noise cancelling headphones and neck pillows, if we want drinks we can buy them or use a credit card that reimburses us as a travel expense….we used to fly coach to make our limited miles go further, but as we get older and our miles pile up the comfort of first class, is easily justified…at least for the sleepy flight…..though I find a non-stop flight with no layovers that provides the quickest time to be the top consideration.

  18. I don’t have infinite miles, so I maximize them by flying coach, and making sure I get an aisle seat. I’d rather make lots more trips and enjoy the destinations than use up my miles just to sit somewhere else on the same plane, or even worse, on a plane with a less desirable schedule. I can see that someone with unlimited ability to get miles, or whose schedule only allows severely limited travel time anyway, might feel differently.

  19. My husband and I have been flying to Hawaii since the 1980’s. Until last year we lived in FL so the total travel time drove our decisions, not class of service. We moved to PHX last year and learned HA offered nonstops flights from Sky Harbor airport to HI. For us, having done the grunt itineraries from FL, it was like a gift from the gods to find ourselves on a nonstop. We decided, in our old age, to treat ourselves to F on HA, RT. The redemption rate was 80K/pp. While we enjoyed the F experience on HA, when all was said and done, we concluded it wasn’t worth the amt of miles it took. Coach class would have been fine. Thus, our attitude is get there fast and take it slow. And, don’t squander our miles just to be “pampered” for a few hours. Flight schedules matter, big time.

  20. As far as I’m concerned, if the seats don’t lie-flat, it’s not First or Business Class! In this instance, Coach is a better value, ESPECIALLY if it has a better schedule.

  21. My grandma (86) and aunt are going to HNL in a few months on a Delta One first class lay-down seat. They have to connect in Atlanta one way, and Minneapolis the other way to do that, but I think/hope it will be worth it for them. At her age, she says this is a once-in-a-lifetime trip and she’s going in style and comfort and I’m thrilled for her!

    This is a cash booking.

    For us, whenever we go to Hawaii (not planning any time soon but ya never know) we will most likely be in coach on the best timetable we can get.

    • The DeltaOne experience to and from HNL is beyond all expectations. It is an awesome product, good food, friendly crew, and Mai Tais!

  22. Usually when I book economy and inquire about the upgrade to business or first, it’s usually more than a couple thousand dollars difference. I never do it then. What am I doing wrong? How do people pay only a little more for an updgrade or upgrade with only miles?

  23. I’m actually having this exact debate with myself right now. We are tentatively planning a trip to Hawaii from the west coast in 4-5 months with our baby and at least one set of grandparents. Booking a direct flight on HA in coach (my favorite way to fly coach) is easy, but trying to get everyone into F becomes much more complicated. However, I do feel like I save up my points and miles so I can spoil myself, even if just a little bit, when I travel on vacation.

    One thing I was thinking about was booking Hawaiian F through Korean Air (UR transfer partner), for 30K miles each way, instead of the 40K, but the procedure seems complicated. Has anyone ever tried this?

  24. We had SAAver business award tickets LAX to LIH, then back home out of OGG. Had a hopper booked on Hawaiian to get from LIH to OGG and the hotel. Hawaiian cancels the flight (only one on a Sunday afternoon), and wants to route us through HNL. Will be our first trip with the baby (he will be 6 months). We said another connection will be too long of a day. So refunded the Hawaiian, re deposited the SAAver awards, and bought tickets direct to OGG in first on UA for $720 each. Saves 5 hours of travel, we can go a day earlier, and save the 80,000 miles. No brainer at the end of the day.

  25. I have never flown first, business, economy plus, anything fancy really. It’s always my 3 year old and myself flying. I just cannot afford it. We are flying economy pdx-ORD-LHR-ORY this summer in economy for like 23hrs. It’s the only way I could afford to go on a Europe vacation.

  26. West of the Rockies, AS is your best bet. Not for F, but for their Preferred Plus seats. 12.5k Avios + $79 is the oneway cost from any of their westcoast gateways, plus whatever it costs for you to reach the gateway. That way you don’t have to connect in HNL if that’s not your destination.

    East of the Rockies, then domestic F is worth the splurge, but only at 60k KrisFlyer miles r/t. Of course you’re restricted to *A in that case but availability is the best of the legacies and all transferable points partner with KrisFlyer. But you’ll probably have to connect in HNL.

  27. This thread has been really interesting, especially to hear from those that live in Hawaii and travel these routes often, like @Cheri and @Darlene.

    We fly SFO/OAK to HNL once or twice a year usually to see my parents. Last year we made the mistake of flying United F and my older daughter (then aged 4 1/2) was miserable because she couldn’t get comfortable in the recliner seat. Her feet weren’t/aren’t long enough to touch the ground (or non-existent footrest) and the seat itself didn’t recline enough where she could curl herself up. When we are in economy, we usually just raise the arm rest and she’ll sleep with her head on my lap.

    Even though United now offers lie-flat seating on a few flights per day on the 777-200s and on Hawaiian on select flights, from the Bay Area it doesn’t seem worth it to invest in the first class seat for somewhere between 4-6 hours. (I’m sure I’d be the first in line for Delta One on the 12-hour JFK-HNL flight though.) For now, we will always select the cheaper, direct flight in economy where the arm rests can be raised and hope that our kids will pass out at some point during the flight. Then we’ll use the miles banked for a J seat on an international trip on CX or JL.

    Good luck with your flights to Hawaii!

  28. Fifth year this year SMF-LIH. Second time using HA. (United last three years). We lucked out last year with an equipment swap to a 757 with lie-flat. This year looks like theyre running 737s again. No-go. Problem is that the best return options are overnight, and I prefer a lie flat for those. This year we’re E outbound and F on return… but a daytime flight. It’ll be our first time domestic F outside of UA, so looking forward to compare.

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