Travel hacking strategy - now have points, but which ones to redeem?

[Begonia]

Hi All,

I'm excited about redeeming my first trip after churning a couple of cards and getting points/miles galore, but I want to make sure I'm doing it strategically. Any advice is appreciated! Here's the story:

I need to book a RT flight from SFO to Vancouver, Canada in December, and I have three redeem options for the dates I'm going:

**Capital One Venture - would cost me 46, 7000 miles for the RT - I'm short 400 points to use my miles but could pay for trip with my VO card and redeem retroactively. This would effectively wipe out my points earned.

**Chase Sapphire Preferred Ultimate Rewards - would cost me approx 37,700 points - my total balance is 63,700 so I'd be left 30K points to play with. Clearly the most economical option, but those UR points are so valuable and I'm not sure if I should use them for this trip. I will be traveling to Canada again, and have other domestic trips in mind.

**United Miles - would cost me 50,000 miles plus $100 - my total balance now is 96,000, so I'd have about 45K left in the United bank - clearly the least economical but since I have the most of these points to spend and they expire 4/16, maybe not a bad way to spend them? However, maybe the best use is this trip to India or Europe next year that I keep thinking about.

I'm tending towards the Venture One miles, which were pretty much all gained through sign-up bonus and points from a few months' expenses. THis is why we do this, right?

Thanks for your thoughts!

[NotJen]

It would help to get a handle on the future trips you have planned.  I have a spreadsheet with my planned trips (some more definite than others), and the points/miles I want to use for each one - it helps me decide what to use where.

For the Venture and UR points, they are more flexible than airline miles, right?  Do they have good cashback redemption options if you don't have a lot of travel planned?  Is it easier to earn miles on one versus the other?  That might make their relative value different - I try not to compare "straight" point values from one program to another because the difficulty of earning more points should be factored in.

FYI, you can usually extend the expiration date on your airline miles by making a purchase through a shopping portal or dining program.  For United miles, I recently downloaded the MileagePlusX app - I bought a gift card through it ($11 at Panera!) and received 55 miles, extending the expiration date of all my United miles into 2017.  On American, I use their dining rewards program, which gives me some miles automatically when I use any of several credit cards to pay at a few restaurants in town (I don't let this decide where to eat, but enjoy adding a few miles to my account when I randomly hit one every few months).

Otherwise - I do like the idea of using the Venture One miles, especially if it wipes them all out so you don't have to worry about using the rest, and you keep your other miles intact for future trips that might cost more.

[Begonia]

@NotJen -

I'm a bit lazy with the details of each card, so I appreciate your thoughtful response. I closed my United Mileage Plus card to avoid annual fee so not sure how to reup expiration - will look into it tho... I assume you can only use a mileage plus card for a purchase through the app portal you mention in order to have effect on expiration? Good stuff with planning trips and designating the miles to use ahead of time. I'll get to this once my workload lessens in next few weeks.  Think I'll go for the Venture One miles for my December trip and have a clean slate, so to speak.

Thanks for the inspiration!

Begonia

[NotJen]

No, you can use any credit card!  My United credit card is closed, too.  I used a Visa card that gets 2% cash back on dining to "double dip" - I got $.22 cash back and 55 United miles for my Panera gift card purchase.

Here's how to earn United miles without flying:
https://www.united.com/CMS/en-US/Marketing/CustComm/Promotions/Pages/earnmileseveryday.aspx#retail
There are tons of options - even I don't want to go through them all!  I also started doing e-Miles a long time ago, so my original plan was to transfer 500 of those points to United to keep my miles from expiring.  That doesn't require any spending at all.

[iamlindoro]

**Chase Sapphire Preferred Ultimate Rewards - would cost me approx 37,700 points - my total balance is 63,700 so I'd be left 30K points to play with. Clearly the most economical option, but those UR points are so valuable and I'm not sure if I should use them for this trip. I will be traveling to Canada again, and have other domestic trips in mind.

Remember that the best use of Ultimate Rewards miles is not to directly redeem them for travel-- ~38K points for that trip actually a terrible redemption.  One better redemption that comes to mind would be to transfer to British Airways Avios (at 1:1), then fly SFO-SEA-YVR, for 12,000 Avios per direction (7500 SFO-SEA, 4500 SEA-YVR, 24,000 total RT). 

Your real problem is that you waited until this close to your trip to redeem.  Points are awesome, but availability is always limited so to get the best redemptions, you should be redeeming ~11 months out.  Were it me in the same boat, I would just pay for this flight with cash and save the miles for a trip with more room to maximize their value.

[klystomane]

Are you planning on keeping any of the fee based ones past the first year?

Unless you have a lot of upcoming trips, I would go by when you "have to" use up my points by if you plan on cancelling to avoid the fee starting in year two.

[Begonia]

@NoJen - Love it. Thanks - will do.

@iamlindoro - Thanks -  Points well taken (pun not intended). By "economical" I meant by the points needed to spend, although I realize it's more complex. Need to step up my game and work with Avios and get into nitty gritty of transferring UR points for redemption with airlines, etc. Will explore your suggestion for future. Great idea. Meanwhile, this last minute trip is a must so I'm working with what I've got.

@klystomane - Not sure about Venture One - was planning on closing it actually because  have closed other cards so I can move on and not deal with fees. Again, more thinking to do.

Appreciate the feedback - have a great weekend , all!