I love credit cards so much!

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We leave for WDW in 3 weeks (myself, 3 girls, my folks). My husband just told me to buy him a ticket as he will leave Thursday and return Sunday night. Problem now is that this late and those dates makes flights expensive. Between us we have about 50,000 sky miles and 250,000 UR rewards. Ultimate goal is a trip to Costa Rica or New Zealand for the two of us within the next year or two. As a hub city Delta always works best. Flight will be about $600 or 50,000 miles. How would you book the flight? Use up pretty much all the sky miles or take some UR points?

I keep going back and forth and can't decide. I just wish he had decided earlier he could go!

My only thought is that UR points are more flexible than Delta skymiles, so I would probably use the skymiles now if you can.
 
I have a new travel goal and need some hacking help please! Goal is a split stay at WDW/Universal in February of 2018.

My planning is currently being thwarted by not being able to access Feb 2018 dates on either the WDW site or the AmEx travel site. Dos anyone know if there's a way to access those dates, or are they just not available yet?

My dream plan would be two nights at the Poly and one night at a Universal hotel (for the early entry).

I'm thinking my best bet for "hacking" some of the hotel costs is going to be travel rewards cards like the Barclay arrival. Any others I should htink about?
 
We leave for WDW in 3 weeks (myself, 3 girls, my folks). My husband just told me to buy him a ticket as he will leave Thursday and return Sunday night. Problem now is that this late and those dates makes flights expensive. Between us we have about 50,000 sky miles and 250,000 UR rewards. Ultimate goal is a trip to Costa Rica or New Zealand for the two of us within the next year or two. As a hub city Delta always works best. Flight will be about $600 or 50,000 miles. How would you book the flight? Use up pretty much all the sky miles or take some UR points?

I keep going back and forth and can't decide. I just wish he had decided earlier he could go!

I'd use the Sky Pesos. UR points are worth more. The only time I have ever used UR points over Sky Pesos was to book a flight to Iceland. Delta was the only option for a lie flat seat. However they wanted 700,000 Sky Pesos for 2 seats. I was not going to transfer that many SPG points, MR and clear out my own bank of Sky Pesos for one trip. I wound up using UR in that case. Had the choice been 300,000 Sky Pesos vs 100,000 UR I would have used the Delta miles.

Is there a limit to how many AA gift cards you can use at a time? I'm pretty sure SW and Delta both have some kind of limit--wondering if AA is the same.

I think it is 6 or 8.
 
We leave for WDW in 3 weeks (myself, 3 girls, my folks). My husband just told me to buy him a ticket as he will leave Thursday and return Sunday night. Problem now is that this late and those dates makes flights expensive. Between us we have about 50,000 sky miles and 250,000 UR rewards. Ultimate goal is a trip to Costa Rica or New Zealand for the two of us within the next year or two. As a hub city Delta always works best. Flight will be about $600 or 50,000 miles. How would you book the flight? Use up pretty much all the sky miles or take some UR points?

I keep going back and forth and can't decide. I just wish he had decided earlier he could go!

I'd keep the UR points since they're more flexible

And if it's just the two of you to Costa Rica, check out Caravan tours. Best vacation I've ever had.
http://www.caravan.com/tour/costa-rica
 

I mulled over Marriott vs SPG. I went with the AMEX SPG which doesn't have as high of a sign up offer right now (I got the 35k). However the way I looked at is for average spending you get 1 SPG point per dollar with AMEX or 1 marriott point per dollar with Chase. To transfer to SPG you need 3 Marriott points making the 1 SPG point on the AMEX more valuable. Not sure if that makes sense but it was how I looked at it!

i was in the same shoes as you, but i have a choice between 35k SPG or 100k Marriott. I hold the quadfecta. I am kinda wanting to branch out to other credit card cards as the majority of my cards were Visa(cuz of chase). 105k points with Marriott isnt too bad either.
The only thing that marriott wins is that its got a free night attached to it. But they way i saw it, Marriott nights are expensive compared to SPG nights.
i mainly did it because i wanted an amex card. haha
 
i was in the same shoes as you, but i have a choice between 35k SPG or 100k Marriott. I hold the quadfecta. I am kinda wanting to branch out to other credit card cards as the majority of my cards were Visa(cuz of chase). 105k points with Marriott isnt too bad either.
The only thing that marriott wins is that its got a free night attached to it. But they way i saw it, Marriott nights are expensive compared to SPG nights.
i mainly did it because i wanted an amex card. haha
I agree, Marriott seems more expensive points-wise, than SPG. I have SPG Amex already & signed up for Marriott card to transfer points to SPG. Does the free night kick in after 1st anniversary?
 
Are there lots here who have both the AmEx Plat and the CSR and are keeping both? DH and I botha already have CSR. It's going to be a keeper card for at least one of us (we'll downgrade one of them eventually), so I'm just not sure if the Plat really makes sense for us. I know MRs are flexible like URs are. I'm kind of afraid of letting that 100K offer pass me by. I'm just trying to work out what I'd be able to do with them in order to stomach that $550 AF.

We wouldn't really be able to utilize the monthly Uber credit as we live in a very small town that doesn't have Uber or a need for it. I have used Uber on some small weekend trips though, so that might be an option, but it wouldn't be used to it's potential for sure. We've yet to really fly much, but it's something I'd definitely want to start doing. Our home airport is MSY in New Orleans, and Southwest seems to be able to get us to all of the destinations I've been looking into recently, which is why I've been working on CP. Want to be able to fly us to DW instead of driving. Plus, we can fly SW to Vegas next February. Don't think we'd really take advantage of the lounge features either. I did tell DH I'd like to eventually plan a Hawaii trip with him, as it's a place we've always wanted to go but it felt out of reach. Our 10th anniversary is in March 2019, so maybe we can try to pull that off and MRs could be a good option for that kind of trip. I guess I need to read up way more on this card before I make a decision. It is very appealing, but I have to feel justified in getting it before I pull the trigger.
 
I see United MileagePlus has extended their targeted MileagePlus Explorer 70k bonus signup offer to June 26. I cannot for the life of me manage to get targeted for this offer. I'd jump on it if I could! I've tried the 70k links, dummy bookings, dummy bookings using miles, making purchases on MPX -- at best, 50k + $50. I have a feeling it's because I already have the MileagePlus Select card and I'm sitting on over 400k miles. My wife who detests United (completely apart from their month from hell), however, is targeted for 70k but refuses to apply and avoids flying United whenever she can (nevermind that we could use the miles on partner airlines). I guess the upside is she's saving one of her 5/24 slots? Any ideas?
 
Are there lots here who have both the AmEx Plat and the CSR and are keeping both? DH and I botha already have CSR. It's going to be a keeper card for at least one of us (we'll downgrade one of them eventually), so I'm just not sure if the Plat really makes sense for us. I know MRs are flexible like URs are. I'm kind of afraid of letting that 100K offer pass me by. I'm just trying to work out what I'd be able to do with them in order to stomach that $550 AF.

We wouldn't really be able to utilize the monthly Uber credit as we live in a very small town that doesn't have Uber or a need for it. I have used Uber on some small weekend trips though, so that might be an option, but it wouldn't be used to it's potential for sure. We've yet to really fly much, but it's something I'd definitely want to start doing. Our home airport is MSY in New Orleans, and Southwest seems to be able to get us to all of the destinations I've been looking into recently, which is why I've been working on CP. Want to be able to fly us to DW instead of driving. Plus, we can fly SW to Vegas next February. Don't think we'd really take advantage of the lounge features either. I did tell DH I'd like to eventually plan a Hawaii trip with him, as it's a place we've always wanted to go but it felt out of reach. Our 10th anniversary is in March 2019, so maybe we can try to pull that off and MRs could be a good option for that kind of trip. I guess I need to read up way more on this card before I make a decision. It is very appealing, but I have to feel justified in getting it before I pull the trigger.

DH and I each have the CSR and each have an Amex Plat business card. I will be adding the Amex Plat personal card which I have had before but got an offer to apply and get it again. We will certainly be keeping both CSR cards and at least one business Plat card. Whether or not the personal one will be a keeper remains to be seen. You can always get the card for the 100k bonus which is worth doing and then decide over the course of the year whether or not to keep it. If you decide not to keep it and did not take advantage of your MR points then open a no fee Amex Everyday card before closing the Amex Plat card to keep your MR points alive. I did this the first time I got the Amex personal Plat.

Hawaii is very do-able with travel hacking and planning. DH and I made our first trip to Hawaii and stayed at Aulani last month. Our flights were on miles and points and our taxes and fees were $5.60 each way and we flew in first class to boot. It took 2 years of planning as I wanted to have a plan A and plan B. We allowed ourselves one year to accumulate the miles and points so that they would all be in place one year before booking flights.
 
I see United MileagePlus has extended their targeted MileagePlus Explorer 70k bonus signup offer to June 26. I cannot for the life of me manage to get targeted for this offer. I'd jump on it if I could! I've tried the 70k links, dummy bookings, dummy bookings using miles, making purchases on MPX -- at best, 50k + $50. I have a feeling it's because I already have the MileagePlus Select card and I'm sitting on over 400k miles. My wife who detests United (completely apart from their month from hell), however, is targeted for 70k but refuses to apply and avoids flying United whenever she can (nevermind that we could use the miles on partner airlines). I guess the upside is she's saving one of her 5/24 slots? Any ideas?

well, u can book *A airlines with UA miles... :]
 
Are there lots here who have both the AmEx Plat and the CSR and are keeping both? DH and I botha already have CSR. It's going to be a keeper card for at least one of us (we'll downgrade one of them eventually), so I'm just not sure if the Plat really makes sense for us. I know MRs are flexible like URs are. I'm kind of afraid of letting that 100K offer pass me by. I'm just trying to work out what I'd be able to do with them in order to stomach that $550 AF.

We wouldn't really be able to utilize the monthly Uber credit as we live in a very small town that doesn't have Uber or a need for it. I have used Uber on some small weekend trips though, so that might be an option, but it wouldn't be used to it's potential for sure. We've yet to really fly much, but it's something I'd definitely want to start doing. Our home airport is MSY in New Orleans, and Southwest seems to be able to get us to all of the destinations I've been looking into recently, which is why I've been working on CP. Want to be able to fly us to DW instead of driving. Plus, we can fly SW to Vegas next February. Don't think we'd really take advantage of the lounge features either. I did tell DH I'd like to eventually plan a Hawaii trip with him, as it's a place we've always wanted to go but it felt out of reach. Our 10th anniversary is in March 2019, so maybe we can try to pull that off and MRs could be a good option for that kind of trip. I guess I need to read up way more on this card before I make a decision. It is very appealing, but I have to feel justified in getting it before I pull the trigger.

I have both the CSR and Platinum and plan to keep both at least for the foreseeable future. My wife also has her own CSR and is an AU on my Platinum.

We both got the CSR for the 100k UR signup bonuses, but have since found it to be an invaluable card. The 3x bonus categories for dining and travel is well suited for our lifestyle and make this card a very fast earner. Of course, this means paying two $450 annual fees but we have no problem using up the $300 travel credit on each of our cards, lowering the effective cost to $150 each. If we were to cancel one of the CSRs and put one of us on the other card as an AU, we'd be paying another $75 anyway, which practically lowers the cost to maintain an additional CSR at another $75. That's ok with us.

If you got a 100k MR bonus offer from Amex for the personal Platinum, go for it if only for the points. I believe that's the max offer for that card. Of course, see if you can go for this offer after you've finished with your Chase cards when you drop below 5/24 soon. (Although, I've read that new Amex cards can take a month or two to show up on your credit report and you can sneak in a Chase app or two before a new Amex gets reported. My new Amex from mid-February was finally reported this month.)

I wish I had gotten a 100k offer for my Platinum, but I've never been targeted despite trying, so I finally settled for a 75k incognito offer. I did it mainly to pad my MR points, which had gotten pretty low. The plan is to eventually transfer my MR points to Hawaiian Airlines miles when a 25% transfer bonus comes around again. Like @calypso726 said, it takes some advance planning. If a transfer bonus doesn't happen before we have to book our flights for our Hawaii trip later this year, those points will still be there for the next time. Hawaiian is our preferred airlines to Hawaii and we try go every year, so the bonus is like two free roundtrip tickets. I also made use of the Platinum's airline credit by purchasing two $100 Hawaiian Airlines gift certificates, and I guess that's how I'll be spending the card's $200 airline credit every year.

I also got the Platinum for Centurion Lounge access because my wife has been flying increasingly for work. I'll keep the Platinum because we fly out of SFO so we have a Centurion Lounge here, which we prefer to the Air France/KLM lounge offered by Priority Pass. I don't think you have a Centurion Lounge at your home airport, so this probably won't be a deciding factor. It's a little sad to think I'm keeping the Platinum as a glorified lounge pass, but otherwise the benefits aren't too compelling for me. It's not a fast points earner at all. I don't find myself or my wife using the 5x bonus on flights and hotels; and the Platinum is 1x for everything else. Automatic Hilton and SPG Gold status is nice. I haven't used the Platinum's Concierge service, but if we didn't have a toddler who's too young and high energy to sit still, I'd definitely call Concierge for Hamilton tickets or French Laundry reservations. Uber... HA! I hate the company and their whole business model, but find myself having to use up the meager $15 Uber credit Amex throws at me every month to justify the new $550 annual fee. That's $200 a year! So I treat the family to delivery by Uber Eats once a month at a $15 discount and pay for the rest using my CSR, which codes as 3x travel.

And that kind of goes to the problem with the Platinum: I don't really have any reason to use it to pay for anything when I can put it on the CSR. For dining and travel, the CSR has the Platinum beat with 3x bonuses. Add in our Chase Freedom with rotating 5x categories. For shopping, the CSR offers price protection (Amex doesn't) in addition to product and return protection. So I find myself just putting a lot of recurring charges on my Platinum -- at least for services that accept Amex -- and my nice shiny, new metal Platinum card has barely been swiped.

Anyway, I agree with @calypso726. Get the Platinum for the 100k bonus and if you don't find enough value in the card to justify the high annual fee, downgrade to an Everyday card to keep your MR points, or call up Amex around when your next annual fee posts to see if they won't give you some kind of retention offer.
 
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So, YIPPEE, I got approved for the Ink BP!! I need to spend 5k now. I was planning to do what I have been doing to meet min spends...putting anything and everything on the card, buying so GC's, maybe paying my mortgage through Plastiq if getting desperate, etc. But now Chase has sent that letter telling people not to use their biz card for personal spend. Ugh, I cannot meet 5k at just Staples and Office Max. What sort of expenses should I NOT put on it to be safe? My biggest monthly expenses are my mortgage and groceries.
 
DH and I each have the CSR and each have an Amex Plat business card. I will be adding the Amex Plat personal card which I have had before but got an offer to apply and get it again. We will certainly be keeping both CSR cards and at least one business Plat card. Whether or not the personal one will be a keeper remains to be seen. You can always get the card for the 100k bonus which is worth doing and then decide over the course of the year whether or not to keep it. If you decide not to keep it and did not take advantage of your MR points then open a no fee Amex Everyday card before closing the Amex Plat card to keep your MR points alive. I did this the first time I got the Amex personal Plat.

Hawaii is very do-able with travel hacking and planning. DH and I made our first trip to Hawaii and stayed at Aulani last month. Our flights were on miles and points and our taxes and fees were $5.60 each way and we flew in first class to boot. It took 2 years of planning as I wanted to have a plan A and plan B. We allowed ourselves one year to accumulate the miles and points so that they would all be in place one year before booking flights.

I have both the CSR and Platinum and plan to keep both at least for the foreseeable future. My wife also has her own CSR and is an AU on my Platinum.

We both got the CSR for the 100k UR signup bonuses, but have since found it to be an invaluable card. The 3x bonus categories for dining and travel is well suited for our lifestyle and make this card a very fast earner. Of course, this means paying two $450 annual fees but we have no problem using up the $300 travel credit on each of our cards, lowering the effective cost to $150 each. If we were to cancel one of the CSRs and put one of us on the other card as an AU, we'd be paying another $75 anyway, which practically lowers the cost to maintain an additional CSR at another $75. That's ok with us.

If you got a 100k MR bonus offer from Amex for the personal Platinum, go for it if only for the points. I believe that's the max offer for that card. Of course, see if you can go for this offer after you've finished with your Chase cards when you drop below 5/24 soon. (Although, I've read that new Amex cards can take a month or two to show up on your credit report and you can sneak in a Chase app or two before a new Amex gets reported. My new Amex from mid-February was finally reported this month.)

I wish I had gotten a 100k offer for my Platinum, but I've never been targeted despite trying, so I finally settled for a 75k incognito offer. I did it mainly to pad my MR points, which had gotten pretty low. The plan is to eventually transfer my MR points to Hawaiian Airlines miles when a 25% transfer bonus comes around again. Like @calypso726 said, it takes some advance planning. If a transfer bonus doesn't happen before we have to book our flights for our Hawaii trip later this year, those points will still be there for the next time. Hawaiian is our preferred airlines to Hawaii and we try go every year, so the bonus is like two free roundtrip tickets. I also made use of the Platinum's airline credit by purchasing two $100 Hawaiian Airlines gift certificates, and I guess that's how I'll be spending the card's $200 airline credit every year.

I also got the Platinum for Centurion Lounge access because my wife has been flying increasingly for work. I'll keep the Platinum because we fly out of SFO so we have a Centurion Lounge here, which we prefer to the Air France/KLM lounge offered by Priority Pass. I don't think you have a Centurion Lounge at your home airport, so this probably won't be a deciding factor. It's a little sad to think I'm keeping the Platinum as a glorified lounge pass, but otherwise the benefits aren't too compelling for me. It's not a fast points earner at all. I don't find myself or my wife using the 5x bonus on flights and hotels; and the Platinum is 1x for everything else. Automatic Hilton and SPG Gold status is nice. I haven't used the Platinum's Concierge service, but if we didn't have a toddler who's too young and high energy to sit still, I'd definitely call Concierge for Hamilton tickets or French Laundry reservations. Uber... HA! I hate the company and their whole business model, but find myself having to use up the meager $15 Uber credit Amex throws at me every month to justify the new $550 annual fee. That's $200 a year! So I treat the family to delivery by Uber Eats once a month at a $15 discount and pay for the rest using my CSR, which codes as 3x travel.

And that kind of goes to the problem with the Platinum: I don't really have any reason to use it to pay for anything when I can put it on the CSR. For dining and travel, the CSR has the Platinum beat with 3x bonuses. Add in our Chase Freedom with rotating 5x categories. For shopping, the CSR offers price protection (Amex doesn't) in addition to product and return protection. So I find myself just putting a lot of recurring charges on my Platinum -- at least for services that accept Amex -- and my nice shiny, new metal Platinum card has barely been swiped.

Anyway, I agree with @calypso726. Get the Platinum for the 100k bonus and if you don't find enough value in the card to justify the high annual fee, downgrade to an Everyday card to keep your MR points, or call up Amex around when your next annual fee posts to see if they won't give you some kind of retention offer.

I was hoping both of you would chime in as I thought I had seen you both post about having CSR and the Plat. I have a few cards from before I learned about this game (Discover It, Citi Double Cash, BofA Cash Rewards, Amex BC and some store cards). I got my CSR in January and immediately realized it's a keeper for me. 3x on dining is a huge plus for us as we eat out quite a bit. Haven't really taken advantage of the 3x travel a whole lot yet, except for paying for a bus we are renting for a family/friends cruise with 34 people in July. That was a nice return to get 3x points on a $1500 charge, then have the family pay me their portions in cash. Hoping to take advantage of 3x travel more in the future as we start traveling more. The CSR and Disney Visa are the only Chase cards I have. With the CSR beating out the Plat as far as earning potential, it's been hard for me to justify going for the Plat because I'm not sure I see myself really putting spend on it outside of meeting minimum.

I'm at 6/24 now, but will be 4/24 in July, so my original plan was to at least add one more Chase card for me - maybe the CIP or CSP (or both). If I do decide to get the Plat, I'll only be back to 5/24 come July. My next card isn't dropping until the end of November so it would be the end of the year before I'd be able to add another Chase card. Darn 5/24 rule........and darn being uninformed on all this and getting other less rewarding cards. As much as I want to focus on Chase, my prior credit cards are making this pretty difficult with the 5/24 rule. On the other hand, I haven't seen any super sweet sign-up bonuses on Chase cards (like the 100k CSR) that would be easier for me to get. Maybe I should go ahead and jump on the Plat and worry about Chase more next year. I can take your advice and at least try it out for a year.

DH is finally on board way more with our credit card activities as of late. He was very much against it in the beginning, but he started to come around quickly as we've been able to plan and book more trips I mentioned the Plat to him already and he didn't really say too much. Haven't broken the $550 AF news to him yet though....LOL. With several DW trips planned over the next 12-18 months, I know we'll be wanting to branch out to different types of vacations. We have the cruise in July, then Vegas in February. I'm going to make Hawaii in March 2019 my next goal since it seems like the perfect anniversary trip for us. I talked to DH about it and he said he's definitely on board for that, so I want to get started with planning ASAP. That will give me just under 2 years to accumulate points and plan everything out. I better start researching my butt off to make the most of this. I'd appreciate any tips/insight you guys might be able to provide on the best strategies for this kind of trip.
 
So, YIPPEE, I got approved for the Ink BP!! I need to spend 5k now. I was planning to do what I have been doing to meet min spends...putting anything and everything on the card, buying so GC's, maybe paying my mortgage through Plastiq if getting desperate, etc. But now Chase has sent that letter telling people not to use their biz card for personal spend. Ugh, I cannot meet 5k at just Staples and Office Max. What sort of expenses should I NOT put on it to be safe? My biggest monthly expenses are my mortgage and groceries.

Isn't your mortgage what pays for your home office?
 
I was hoping both of you would chime in as I thought I had seen you both post about having CSR and the Plat. I have a few cards from before I learned about this game (Discover It, Citi Double Cash, BofA Cash Rewards, Amex BC and some store cards). I got my CSR in January and immediately realized it's a keeper for me. 3x on dining is a huge plus for us as we eat out quite a bit. Haven't really taken advantage of the 3x travel a whole lot yet, except for paying for a bus we are renting for a family/friends cruise with 34 people in July. That was a nice return to get 3x points on a $1500 charge, then have the family pay me their portions in cash. Hoping to take advantage of 3x travel more in the future as we start traveling more. The CSR and Disney Visa are the only Chase cards I have. With the CSR beating out the Plat as far as earning potential, it's been hard for me to justify going for the Plat because I'm not sure I see myself really putting spend on it outside of meeting minimum.

I'm at 6/24 now, but will be 4/24 in July, so my original plan was to at least add one more Chase card for me - maybe the CIP or CSP (or both). If I do decide to get the Plat, I'll only be back to 5/24 come July. My next card isn't dropping until the end of November so it would be the end of the year before I'd be able to add another Chase card. Darn 5/24 rule........and darn being uninformed on all this and getting other less rewarding cards. As much as I want to focus on Chase, my prior credit cards are making this pretty difficult with the 5/24 rule. On the other hand, I haven't seen any super sweet sign-up bonuses on Chase cards (like the 100k CSR) that would be easier for me to get. Maybe I should go ahead and jump on the Plat and worry about Chase more next year. I can take your advice and at least try it out for a year.

DH is finally on board way more with our credit card activities as of late. He was very much against it in the beginning, but he started to come around quickly as we've been able to plan and book more trips I mentioned the Plat to him already and he didn't really say too much. Haven't broken the $550 AF news to him yet though....LOL. With several DW trips planned over the next 12-18 months, I know we'll be wanting to branch out to different types of vacations. We have the cruise in July, then Vegas in February. I'm going to make Hawaii in March 2019 my next goal since it seems like the perfect anniversary trip for us. I talked to DH about it and he said he's definitely on board for that, so I want to get started with planning ASAP. That will give me just under 2 years to accumulate points and plan everything out. I better start researching my butt off to make the most of this. I'd appreciate any tips/insight you guys might be able to provide on the best strategies for this kind of trip.

I like to consider long term goals and this is where the Chase keeper cards come in. For me they are CSR, Ink+, Freedom and CFU to generate UR points. My other Chase keeper cards are United, Marriott and IHG for the annual nights, lounge passes and access to additional award availability. I also have a Disney and Amazon card that I've had forever so I can't cancel them. They sit in a drawer and are relegated to buying a small purchase each year. If I were starting out now. I'd start with acquiring my Chase keeper cards that are subject to 5/24 while building up my UR points. CSR and CSP with the goal of product changing the CSP to a Freedom. Whatever Ink has a high signup and then downgrading to a no fee or cancelling. I'd want the Marriott card with the 100k and make DH get one too so we have a free weekend each year. Once I had all my Chase cards that I want I'd stop worrying about 5/24 and focus on hitting the other cards. This is what I personally would do, knowing what I know now with how things are now if I had no specific goals. A specific goal would likely turn this on its head.

For your Hawaii trip: First research which airline(s) at your local airport(s) have the most available flights to the Hawaii airport you plan to fly into. Next, identify what alliance they belong to and who are their partners. Then find out how many miles you would need to fly that airline in the class of service you desire. Then find out which variable points UR, MR, SPG, TY transfer to that airline or a one of it's partners and if they are a 1:1 transfer or not. That's your Plan A. Plan B is figure out the same thing but without Plan A. For me that was a pay with points plan (Thank You points) and I wound up using both plan A and B.
 
I'm going to make Hawaii in March 2019 my next goal since it seems like the perfect anniversary trip for us. I talked to DH about it and he said he's definitely on board for that, so I want to get started with planning ASAP. That will give me just under 2 years to accumulate points and plan everything out. I better start researching my butt off to make the most of this. I'd appreciate any tips/insight you guys might be able to provide on the best strategies for this kind of trip.
I was just thinking of this trip myself. 2019 will be our 30th anniversary and it would be a great idea. There's other trips I'd rather do, but they are international & we won't be going out of the country for a while.

The only non-stop Chicago to Honolulu is on United, so I'll be brainstorming how to get 300k miles.
 
I like to consider long term goals and this is where the Chase keeper cards come in. For me they are CSR, Ink+, Freedom and CFU to generate UR points. My other Chase keeper cards are United, Marriott and IHG for the annual nights, lounge passes and access to additional award availability. I also have a Disney and Amazon card that I've had forever so I can't cancel them. They sit in a drawer and are relegated to buying a small purchase each year. If I were starting out now. I'd start with acquiring my Chase keeper cards that are subject to 5/24 while building up my UR points. CSR and CSP with the goal of product changing the CSP to a Freedom. Whatever Ink has a high signup and then downgrading to a no fee or cancelling. I'd want the Marriott card with the 100k and make DH get one too so we have a free weekend each year. Once I had all my Chase cards that I want I'd stop worrying about 5/24 and focus on hitting the other cards. This is what I personally would do, knowing what I know now with how things are now if I had no specific goals. A specific goal would likely turn this on its head.

For your Hawaii trip: First research which airline(s) at your local airport(s) have the most available flights to the Hawaii airport you plan to fly into. Next, identify what alliance they belong to and who are their partners. Then find out how many miles you would need to fly that airline in the class of service you desire. Then find out which variable points UR, MR, SPG, TY transfer to that airline or a one of it's partners and if they are a 1:1 transfer or not. That's your Plan A. Plan B is figure out the same thing but without Plan A. For me that was a pay with points plan (Thank You points) and I wound up using both plan A and B.

Thanks so much! I must say your strategies and travel stories are definitely my goals...LOL. I know it takes time to learn all the ins and outs. I'm hoping I can pick up on all this quickly. Started researching flights to Hawaii and looking at where we might want to stay. I'm so thankful this for this hobby because without it, Hawaii is definitely something we would have had to wait a lot longer to experience.

I was just thinking of this trip myself. 2019 will be our 30th anniversary and it would be a great idea. There's other trips I'd rather do, but they are international & we won't be going out of the country for a while.

The only non-stop Chicago to Honolulu is on United, so I'll be brainstorming how to get 300k miles.

My first search for New Orleans to Honolulu came up with no non-stop flights at all. I'll keep looking, but it seems like we'll have a layover regardless of which airline we end up going with. Might be using those lounge benefits on some cards afterall. LOL. Just want to get the best bang for our buck.
 
My first search for New Orleans to Honolulu came up with no non-stop flights at all. I'll keep looking, but it seems like we'll have a layover regardless of which airline we end up going with. Might be using those lounge benefits on some cards afterall. LOL. Just want to get the best bang for our buck.
I'm not a fan of layovers although sometimes they are the only option. We've missed a connecting flight once and had a few near misses. When we flew to China, we chose United for the sole reason it had the only nonstop flights from Chicago at the time. Plus DS is 8, and entertaining him during a layover just adds more stress.
 
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