At this point my plan is to fly to from EWR to HNL on United, business class, stopping at LAX on the way there and back. This would be July or the month of August (I wish it could be 2018 but I'm sure it will have to be 2019). I'd do a stop for 4 days on both ends in LAX (
Disneyland and other destinations), with 7 nights in Hawaii.
I wish I could do a search to see what a Business class reward ticket would be, but since I don't have a United credit card they won't show me. Does anyone think I could get one ticket for 100k miles? I'm hoping it's not 200k since it's multi destination. The goal is to buy two tickets and use miles for the other two. I wonder how long it would take to save that up if I strategically open the right Chase accounts. I don't think AMEX points will help me for United.
Anyone have any input? Thanks!
You'll probably be better off looking at them as two separate tickets. You have your EWR to LAX round trip and your LAX to HNL round trip. Doing them this way doesn't force you into just using United for any of the flights. For that matter you could look into the EWR to/from LAX as one ways and use SNA or Long Beach for one or both of the flights depending on where you are staying. LAX to HNL should give you more options aside from just United, though I'm not sure Hawaiian flies nonstop from LAX I can't imagine there's only one airline that flies non stop to HNL from LA since I'm pretty sure I have at least 2-3 options to Hawaii from Seattle.
I agree with
@afan completely. You'll want to consider breaking up your trip into two itineraries: EWR<>LAX and LAX<>HNL if you plan to stop over in LA/OC for a few days. EWR (or the greater NYC region)<>LAX is well serviced so you should have some options there. Once you're on the west coast, your flight options to HNL really open up; with LAX being a hub for United, AA, Delta, and Alaska, which all fly routes to HNL, you may have an easier time finding better prices and availability for that portion of your travel. I'm a big fan of Hawaiian Airlines, which also flies LAX<>HNL.
The downside is you're planning to travel in August, which is still considered the peak season for Hawaii travel. This is a time when a lot of families are trying to squeeze in a summer vacation before school starts for their kids and older students are flying to and from the mainland for college. Flying to Hawaii is expensive and there's really no low season, but prices do tend to be less expensive between September through November (except Thanksgiving), and January through April (except the few weeks for spring break) -- basically when kids tend to be in school.
You can check
https://www.awardhacker.com/ for an idea of how many points from different frequent flyer programs it'll cost to fly economy, business, or first class on the different carriers from EWR<>LAX<>HNL, as well as what awards points are transferrable to the airlines. You should also sign up for different frequent flyer programs if you haven't already so you can log into the airlines' sites and search for award flights. We're around the time when flights should already be available for next August.
If you're flying exclusively on United, you'll want to focus on MileagePlus, Chase UR, and SPG (or Marriott) points. (Keep in mind that changes are coming to United's MileagePlus program in November:
https://thepointsguy.com/2017/06/united-everyday-awards/) Focus on that list of Chase's 5/24 cards first (
https://www.doctorofcredit.com/chase-524-rule-explained-detail-need-know/) because once you've opened 5 cards in the last 24 months, you won't be able to go back for them or their bonuses for a while (if ever). Then move onto other cards that can help get you to Hawaii. Amex MR points do transfer to Singapore Airlines, ANA, and Air Canada, which are part of the Star Alliance with United, and you can use them to book United award flights to Hawaii (
https://millionmilesecrets.com/2017...membership-rewards-points-for-hawaii-flights/). You can even get a better value by booking United award flights through Singapore Airlines. MR points also transfer directly to Hawaiian Airlines, and there's usually a 25% transfer bonus promotion once a year that stretches the value of your MR points to Hawaiian (
https://thepointsguy.com/2017/06/amex-to-hawaiian-25-percent-bonus/). Watch out for transfer bonuses to other airlines as well. Hawaiian also has its own credit card through Barclaycard, with a 35k miles public offer and a 50k miles offer that's targeted or triggered with a dummy booking. Hawaiian only has first class and main cabin seats, and 50k HawaiianMiles is usually enough for one LAX<>HNL roundtrip ticket in the main cabin (I think first class is something like 160k), but can be lower if you book early enough or higher if you wait too long. Flight (and award) availability for Hawaiian opens up 330 days out, and other airlines also have schedules available as early as a year in advance. Figure out your dates, then find out when's the earliest you can book award travel for those dates, and put it in your calendar.
So like
@calypso726 suggested, you should try to plan at least two years out -- accumulate as many points as you can so you have them in place to book as soon as award availability opens for your desired airline.