While I'm not a travel hacking expert, I have read a ton of blogs, listened to a lot of podcasts, and completed a couple of online courses since I started one year ago. Based on all I've learned, I think one of the best places to start with earning and using points is to open credit cards that offer Chase Ultimate Rewards points. (Runner up, which I'll discuss below, is going for the Southwest Companion Pass.)
In part this is because the points are easy to earn, easy to combine, and can be transferred to over a dozen travel partners for both flights and hotel stays. The other reason is Chase's 5/24 rule. Chase will only approve you for a new card (both those that earn Ultimate Rewards and specific airline/hotel branded cards, like ones for Southwest and Hyatt) if you have opened fewer than 5 credit cards in the last 24 months. This means five of any credit cards not just Chase credit cards. Starting with Chase cards avoids this issue.
Chase Ultimate Rewards
I've outlined below how you might go about accumulating Ultimate Rewards points, assuming you have a willing partner to act as your Player 2.
Open the Chase Sapphire Preferred or Reserve.
Refer your Player 2.
Player 2 opens Chase Sapphire Preferred or Reserve. --wait about 90 days--
Refer your Player 2.
Player 2 opens Chase Business Ink Cash or Unlimited.
Steps 1 through 3 will give you a total of at least 140,000 Ultimate Rewards points not counting the points you'll accumulate for your spending, potentially more if there are boosted sign-up bonuses when you apply. If you add steps 4 through 6 (most people can qualify for a business card), you'll have a minimum total of 330,000 Ultimate Rewards points.
You can then combine your points with your partner's points and transfer them to any of Chase's 14 travel partners. See my post all about Chase Ultimate Rewards for more information.
Southwest Companion Pass
Another great place to start with travel hacking is to work toward the Southwest Companion Pass. If your primary goal is to fly for nearly free within the US, you really can't beat this. We used the steps outlined below to rack up enough points for 14 roundtrip Southwest tickets in the past year for less than $160 in taxes and fees.
Open Southwest Rapid Rewards Plus card.
Refer Player 2 for Southwest Rapid Rewards Plus card.
Player 2 opens Southwest Rapid Rewards Plus card.
This will give you a minimum of 220,000 Southwest points that you can use to book flights, plus one Companion Pass. The companion pass allows you to book a ticket for one named person to travel with you for free, when you book a ticket with either cash or points. It is good for the remainder of the calendar year in which you earn it and the entire next calendar year. For more detailed instructions on earning, using, and maximizing the value of the Companion Pass, see this blog post.
Note: If you do not have a partner that will act as your Player 2, skip steps 2 and 3 and be sure to open the Performance Business Card. You'll still have enough points for the Companion Pass.
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