Hawaii in Winter

[myls2go]

Okay, so first post here - and in any travel forum really. I've been stalking Reddit/forums for a few weeks now - haven't reached the point of MS or anything and am still charging only legitimate spends to my cards to earn points (yes, super noob).

I thought this would be a good way to join and say hi, while also getting a little help. So Hi! Any help or ideas would be much appreciated.

1. What route are you looking for?
ORD - Hawaii (no preference for an island, but recommendations are welcome)

2. What dates do you want to travel (mention how flexible you are)?
5 days anytime around Dec 13, 2016. Would like to be there on the 13th (anniversary).

3. Do you want to fly first, business, or coach? (maybe also "are you willing to fly coach for a positioning flight")
No preference. Coach, to save on points/miles maybe?

4. How many passengers?
Two

5. How many points do you have, in which programs?
UR - 220,000
TYP - 50,000 (working towards it. Should have it by August)
Hilton HHonors - 75,000 (working towards it. Should have it by August)
AA - 13,000 / 12,000 (Points in my wife's and my account)

At this point, I can't apply for any new cards because I have a new mortgage coming in. I applied for the Prestige and Amex Hilton after asking my loan officer if it would affect my mortgage any and he said it should be fine. I'm also open to a some amount of OOP expense because I don't want to use up ALL my points/miles.

Thanks very much in advance!

 

[MarkD]

Welcome to Saverocity!

Your best bet is to search UA for a direct ORD-HNL flight. You can transfer Chase UR directly to United to book the flights. Availability is good for your dates starting around December 7th/8th and returning on the 13th as you are beating the holiday crowds. It will cost you 22.5K per person each way in coach for a total of 90K.

Once you get to HNL you can take a short island hopper flight (pay cash?) to move to another island if you want.

Hawaii has it all, it just depends what you are looking for. HNL on Oahu is like NYC (lots of activities for everyone + crowds). LIH on Kauai is a lot more quiet (some say boring) and OGG on Maui is a good mix of the two. Kona and Hilo I can't speak for...

Your hotel points may get you one night in a decent Hilton. Look at transferring UR to Hyatt for staying at a Hyatt Place (12K per night) or Hyatt Regency (20K per night) on Waikiki Beach in HNL for example.

 

[MickiSue]

If you have flexibility, and want to make your trip extra special, try for saver first class awards. One of the perks of MS is that you can replace spent miles WAYYYYY faster.

My husband is finally getting used to that line of thinking. That, even if, for example, he spends 62500 on a one way J to visit our daughter at VCE, he can have it back in a couple of months.

Which brings me to my second suggestion. Book one ways, not round trip. Get your outbound set, and then you can figure out what to do for the return. First on the outbound is most important, so you can be rested and feeling pampered right from the moment you arrive at the airport. After all, isn't that what a landmark vacation is about?

If you find a route/time with mixed cabin availability, be sure to check which part of the trip is first. Obviously, you want it the over water portion. IF you can find saver awards for two people in F, the total cost would be only 160K points for a round trip.

In truth, though, this, because it's a special occasion, might be a trip that is worth calling UA customer service, explaining the needs (anniversary, flexible dates with a five day stay, etc) and see if they can help you find something.

 

[myls2go]

Mark,
Thank you for the welcome and all the information. I looked into this over the long weekend as well and it looks like UA, as you have suggested, would be my best bet. I'm contemplating booking with a stopover elsewhere for future travel. I noticed that I have to enter stopover dates while making my booking - any experience in making changes to those dates if I don't know for sure when I can make that "leg" of the trip?

I'm fine with paying cash for hopovers and/or hotels as well. At this point, I'm trying to get the hang of it all so I'm expecting some out of pocket expenses. My Citi Prestige allows me to book a fourth night for free so I'm out a little less money (yay!).

Since this is an anniversary trip, I think I'll pass on the crowds I was thinking maybe Maui for 4 nights and potentially another island (TBD) for a couple.

Will look into booking everything this weekend so wish me luck!

 

[myls2go]

If you have flexibility, and want to make your trip extra special, try for saver first class awards. One of the perks of MS is that you can replace spent miles WAYYYYY faster.

My husband is finally getting used to that line of thinking. That, even if, for example, he spends 62500 on a one way J to visit our daughter at VCE, he can have it back in a couple of months.

Which brings me to my second suggestion. Book one ways, not round trip. Get your outbound set, and then you can figure out what to do for the return. First on the outbound is most important, so you can be rested and feeling pampered right from the moment you arrive at the airport. After all, isn't that what a landmark vacation is about?

If you find a route/time with mixed cabin availability, be sure to check which part of the trip is first. Obviously, you want it the over water portion. IF you can find saver awards for two people in F, the total cost would be only 160K points for a round trip.

In truth, though, this, because it's a special occasion, might be a trip that is worth calling UA customer service, explaining the needs (anniversary, flexible dates with a five day stay, etc) and see if they can help you find something.

Great suggestions and thank you for the response. I checked out first saver and unfortunately it's all mixed cabin with first to SFO and coach after. Both legs are pretty much the same in flight time so it may not be all bad. Obviously, it would've been great if I got first for SFO to OGG.

I will definitely take your suggestion on calling UA.

Ooh, MS. Total newbie here so I'm treading *very carefully* and trying to gather as much information as I can before getting into that game. I only just bought Trader Joe's gift cards to max out my freedom category (we use Joe's so the cards will get used soon enough). But I see your point. Getting back used points is especially easy with the CSP and Freedom combo.

 

[Josh F]

if you have the United CC or elite status, be sure to log in first, you'll see more saver availability.

 

[myls2go]

if you have the United CC or elite status, be sure to log in first, you'll see more saver availability.

Interesting. I don't have either but would you know if I can transfer my UR points to someone else's UA account and book the tickets through their account?

Also, encountered something pretty odd. I was looking for award availability between different islands to see if there was a difference and I randomly came across a one way route from ORD-KOA for 14.5k miles in economy and 20k in first saver. I tried jumping on it but by the time I went back to change the number of flyers (I set this to one. Stupid!), it was gone. The flights went back to 22.5k for economy and 40k for first saver.

 

[Josh F]

Interesting. I don't have either but would you know if I can transfer my UR points to someone else's UA account and book the tickets through their account?

Also, encountered something pretty odd. I was looking for award availability between different islands to see if there was a difference and I randomly came across a one way route from ORD-KOA for 14.5k miles in economy and 20k in first saver. I tried jumping on it but by the time I went back to change the number of flyers (I set this to one. Stupid!), it was gone. The flights went back to 22.5k for economy and 40k for first saver.

Technically, although Chase does have restrictions on who you can transfer your points too (different for their personal vs. business cards). If you violate their transfer rules you run the risk of a shutdown. Additionally, you'd also have to really trust whoever you are transferring too.

No idea on the 14.k miles, never seen that before.

 

[MickiSue]

Clear your cookies. Go back and get one ticket. Clear your cookies. Try for the next ticket.

It's exceedingly rare to be able to book more than one saver award at a time, especially in F or J.

 

[stellar]

Mark,
Thank you for the welcome and all the information. I looked into this over the long weekend as well and it looks like UA, as you have suggested, would be my best bet. I'm contemplating booking with a stopover elsewhere for future travel. I noticed that I have to enter stopover dates while making my booking - any experience in making changes to those dates if I don't know for sure when I can make that "leg" of the trip?

I'm fine with paying cash for hopovers and/or hotels as well. At this point, I'm trying to get the hang of it all so I'm expecting some out of pocket expenses. My Citi Prestige allows me to book a fourth night for free so I'm out a little less money (yay!).

Since this is an anniversary trip, I think I'll pass on the crowds I was thinking maybe Maui for 4 nights and potentially another island (TBD) for a couple.

Will look into booking everything this weekend so wish me luck!

We were in Maui last month - here's my review with suggestions/recommendations:
https://saverocity.com/forum/posts/662552/