If you've been travel hacking for any length of time you likely have access to a range of points currencies and credit cards, each with its own strengths. Rewards programs typically are combined with a specific booking channel: you can only redeem Alaska Mileage Plan miles through the Mileage Plan website, and you can only redeem Chase Sapphire Reserve Ultimate Rewards points for 1.5 cents each through the Ultimate Rewards website.
Under many circumstances, however, it's possible to combine the benefits of multiple programs in order to get the best of multiple worlds.
The simplest example comes when booking an airline award ticket. In addition to the mile component of an award ticket, you'll typically pay a cash component ranging from $5.60 for the simplest domestic one-way flights to hundreds of dollars in fuel surcharges on many international flights.
That cash component gives you the opportunity to choose the right credit card for the job. On the simple end you might use a co-branded credit card in order to earn bonus points. If you have a Barclaycard Arrival+, Bank of America Travel Rewards, or other credit card that lets you redeem credit card rewards towards travel purchases, then such fees are an opportunity to extract value from those points.
Finally, if you have a credit card in the Chase Sapphire family, paying award ticket taxes and fees with a Sapphire, Sapphire Preferred, or Sapphire Reserve triggers their fairly generous trip delay insurance benefits. The Citi Prestige's similar trip delay insurance apparently does not cover award tickets, although it does cover tickets booked using Citi ThankYou points.
It's also possible, albeit trickier, to trigger credit card protections on revenue tickets.
When booking two or more tickets through the US Bank Flexperks Travel Rewards booking channel, you have to redeem Flexpoints towards at least one ticket in each order, while additional tickets on the same order can be paid for with a credit card. Booking a single ticket with Flexpoints and paying for your additional tickets with a Chase Sapphire card would extend insurance coverage to the entire reservation while only paying out of pocket for one ticket.
Flexible and refundable tickets offer another opportunity. Airlines like Southwest and Alaska allow the value of cancelled tickets to be returned to your account and used towards future flights. You could then "top up" the cost of your flights with a Chase Sapphire card and trigger trip delay protections.
This should work with any airline that sells refundable tickets, although you may have trouble finding refundable tickets that are cheaper than the flight you actually plan on reserving, which is necessary in order to have space "left over" to pay for with your Chase Sapphire, or any other, credit card.
One trip insurance benefit people seem to value especially highly is primary rental car collision insurance. Of course, this benefit is only valuable if you get in an accident. If you don't get in an accident, you might prefer to pay with another card, for example in order to redeem fixed-value points against the charge.
This classic post by The Mr. Pickles explains how you can do precisely that: reserve and collect your rental car with whichever card offers the best insurance protection, then upon returning the car change your payment method to whichever card has the highest earning rate or where you have fixed-value points stored up to cover the charge.
Knowing the particularities and peculiarities of each program you participate in, and the requirements for triggering statement credits, insurance coverage, and other credit card benefits, gives you added flexibility in deciding how to get the most value, at the lowest price, from each of your booking decisions.