From personal experience, I'd book a cancelable car now thru discount Hawaii car rentals as a safety

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Managed to get the AA flights and dates we wanted from IAH - DFW - OGG in November for our 40th anniversary for 107,500 miles each for Economy on the outbound and First Class on the return. Had to jiggle around a few miles and buy a few more but am happy that we didn't have to spend too much cash.
From personal hilton doubletree hotels experience, I'd book a cancelable car now thru discount Hawaii car rentals as a safety net. And then watch the rates. That way you're covered. I booked my current rental 6 months out and the rates went up up up.
We fly the AA 767 to OGG via DFW (from Chicago). I use our miles for upgrades to first, thus earning miles for both the purchase on the AAdvantage card and for the miles flown. I will even go via HNL to get that 767 out of DFW. You'll be able to *sleep* on those near-flat hilton doubletree hotels seats in first.
I would also joint the loyalty program of the car rental company you book. I rented cars for years but rented one from a discount company because the rate was great in Kauai. I stood in line with just about every person hilton doubletree hotels on the plane. The other counters were virtually empty and we waited almost an hour. I'm used to going right up to the "fast" line and that's one rental company I was not a member of. As soon as you book, join their frequent renter program so you can go to the short line!
Good idea, starrs. I remember standing in a long line last time we arrived in Maui because we also went thru one of the discount companies hilton doubletree hotels and we weren't members of Budget or whatever rental car company it was. It was definitely a big hassle after traveling for 10+ hrs to get there.
hilton doubletree hotels Just become a member of the XYZ car rental company. It doesn't cost anything. We walk through the National office, pick out a car and hand our reservation information to the guy at the gate to the road. Five minutes later we are on the road.
Hi ChiSue, hilton doubletree hotels sorry to hijack this thread, but what is the mileage cost to upgrade on AA? Do you just buy the lowest price economy fare and then upgrade to first or is there a particular fare type that you have to purchase? Thanks!
To bettyk - congrats on booking Hawaii flights using miles! I've had experience with that many times and in fact going to Kauai in February using Hawaiian Air miles. I reserved a car via Discount Hawaii Car Rental as well, and it was much cheaper than going through any other car rental or third party website. If I find something cheaper closer to the date then I will cancel. Most likely I'll just try priceline, hotwire, Costco, or see if there are any deals with some Citi Thank You points I have. Enjoy your trip! You have plenty of time to plan your activities!
When we upgrade our AA flights, it is usually for flights to Europe. I buy the lowest hilton doubletree hotels economy fare I can find online and then contact the AAdvantage hilton doubletree hotels desk to get on the "wait list" for a Biz Class upgrade. Obviously, the sooner you get your name on the list, the better your chances for getting the upgrade. The cost is $350 each way plus 25k miles for an upgrade from Economy hilton doubletree hotels to Biz Class.
November isn't one of the more difficult 'High Seasons' unless you are visiting over the Thanksgiving holidays. We don't commit our miles until we know we can get the upgrades. We no longer travel a lot, so I want to keep the miles piling up for this annual trip!
tifa2276 -- I meant to add that we have sometimes had to book our outbound for January with a fake return as soon as the airline calendar hilton doubletree hotels opens, then pay a ticket change fee ($200 pp) to grab upgrades two months later when the calendar opens for our March returns. It's worth it to us to be certain of getting first class on a 767 for these long flights: ORD-DFW-OGG. (It's NOT worth it on a 757.)
From what I've read, it's a poor use of miles to use them for car rentals. I've never gotten a better price from Discount Hawaii hilton doubletree hotels than I could get via Costco, and sometimes via AA. That may be because we require longer rentals. This year we are paying about $22/day, all in, for an intermediate car. (I don't care about the car size as long as it has four doors and A/C; cheapest rate gets my business.)
Thanks for the info bettyk and ChiSue. I have been using Hawaiian miles for the past few years, but I do have some AA miles to burn too. I've never done an upgrade using miles so would be a nice treat (but only if its a lie-flat seat!).
AA's 767's out of DFW are not true lie-flat seats, but I can sleep on them. Lord only knows when AA will fulfill its' promises of better flights to and from Hawaii -- or, for that matter, bring back nonstops from ORD to HNL! We are getting too old to wait much longer.