How to Take Your Next Vacation for Free (Or Close to It)
Jason Steele
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"I learned not only could I start racking up points and miles for free travel, but I could often fly in business or first class."

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Back in 2006—after years of spending a lot of money on plane tickets—I was tired of feeling ripped off. So I turned to blogs and online forums, ultimately learning that not only could I start racking up points and miles for free travel, but I could often fly in business or first class.

Eleven years later, I rarely pay for travel, despite taking at least one trip a month—whether it’s a couple days away for business, a Hawaiian vacation with my wife and kids or visiting family in Argentina or Israel.

Always wanted to try it yourself? While it takes time and practice to make your points really pay off, following these basic rules can help get you started—and potentially score your next vacation for (nearly) nothing.

1. Pick the right credit card(s).

A credit card is the most valuable tool for earning points and miles. Look for one with a generous bonus—in the 50,000 to 100,000 range—just for opening an account and completing the minimum spending requirement.

Round-trip domestic flights in economy typically start at 25,000 miles per person, and award flights to Mexico or the Caribbean are around 35,000 miles on United and American. (To search, select “search for award travel” on the airline’s website.) So it’s possible to take care of airfare just by applying for one or two cards. Airline-affiliated cards will also reimburse you for checked bag fees, typically, and provide discounts on in-air food and other purchases.

Don’t forget to research flexible travel cards, too (as opposed to airline- and hotel-specific), where rewards are redeemed as statement credits toward any travel purchase—potentially reducing your costs to zero when used for car rentals or your flight’s taxes and fees.

Related: Before You Pick a Travel Rewards Card, Ask Yourself These Questions

2. Streamline your spending.

Keep growing your rewards by using your card for everyday spending. Some offer special category bonuses—say, 3x points for groceries or gas—so make sure you’re swiping the right card at the right time.

Related: The Best Rewards Cards for Everyone From Budgeters to Foodies and Frequent Flyers

One note of caution: This strategy only works if you pay off the card each month. Paying interest on a revolving balance can quickly erase any benefits.

3. Maximize your rewards.

While you’re working toward a free trip, maximize your rewards on paid vacations. For example, some airlines and hotel chains offer double or triple rewards for booking within a particular timeframe, or for travel to featured destinations. Check their sites and Twitter pages often, as these offers come and go quickly.

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4. Redeem strategically.

Every loyalty program features great ways to redeem rewards and terrible ones—so do some quick math.

For example, with United’s MileagePlus program, it’s possible to snag a 120,000-mile business class flight to Europe. This ticket could easily cost $6,000, meaning you’re getting 5 cents in value per mile redeemed. On the other hand, you’ll only get 1 cent per mile (or less) by redeeming United miles for hotel stays, rental cars and cruises.

It can be tedious, but the more time you’re willing to spend researching options and doing the math (and the more flexible you can be with dates), the more likely you are to get a good deal.

In general, aim for at least 1.5 cents per reward. That means redeeming for things like merchandise or gift cards—typically at a rate of 1 cent per point—is usually a bad deal.



    Hi, I average around $5k a month in expenses with my credit card, which I pay off every month. I use my capital one venture that gives 2 miles per dollar spent. Is there anything better based on my monthly credit card charges?

    Depends on what you’re buying with that credit card. Most have different bonus categories. Venture is good if you don’t want to be hassled with multiple cards and knowing which one to use. However there is apps that will help decide which card to use. Chase Sapphire Reserve is my choice right now. You can still get the 100k signup bonus through march and the perks are pretty great.

    The 100k was the online promo which expired in Jan. However, you can still sign up in-branch and receive this same promo till March 15,2017 🙂

    The Chase Sapphire Reserve has a hefty annual fee, but it’s mostly reimbursed by a $300 travel credit. 3X points on Dining and Travel purchases and your reward points are worth 1.5 cents when you book through their site. It’s GREAT!!! Highly recommend! Can also shop through the Chase site and earn bonus points on your regular spending.

    I have both the Preferred and Reserve Chase cards (recently upgraded to the reserve). The Preferred card is great but for most people reading this you’re probably better off going with the Reserve. The $300 travel credit brings the actual fee for the Reserve down to $150 which is only $51 more than the Preferred. They are very generous with what they consider travel as well: hotels, plane tickets, uber rides, parking…I’ve hit it with all of them. The other thing is you earn 3 points per dollar on travel and dining vs. 2 with the Preferred so you quickly make up that extra $51. The Reserve also has some upgraded perks and I encourage you to see if any of those make a difference for you as well.

    I have found that reserving flights through the Chase Ultimate Rewards system isn’t really worth the points that you get. It’s very limiting as to the possible flights it returns when you search and much more expensive than shopping around on other sites.

    Sometimes when I can’t find a specific flight on the, I call them directly and they are able to pull up flights which are not shown online. Just provide them with the flight number, airline, etc. 🙂

    You can transfer the points to a bunch of other airlines if you’d like 1:1. Sometimes you can even get more value per point this way. I’ve never had a problem finding a decent flight with good value but you might have to do a bit of work.

    I started out with the chase preferred card and cashed in the 50k bonus points for a trip to Belize. Just recently I jumped ship to the reserve card and will be hitting the 100k bonus. Your points do not expire which is great when you are ready to pull the trigger on a good flight deal. Amex recenrtly was offering a 100k bonus. My plan is to bounce from card to card every year or two that has a bonus point deal going on. This will work if you have good credit. Keep in mind with chase if you cancel you are not eligible for that particular card for 24 months after canceling.

    How much are you spending that you travel once a month for free? Do you fly business/first when you do these things? After 3 years in the game I’ve just been able to book a SQ Suites for later in the year. (Though we did LH F and TK J to/from Maldives last year). I guess there are ways I could travel once a month for “free” with the points I have banked now (350K UR, 50K Hyatt, 40K SPG)… but nowhere exotic/extravagant.

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