how to get the most out of your travel dollars 1


1) Airline loyalty pays off. I definitely don’t love Delta, but flying them almost exclusively gets me a lot of benefits, mainly in the form of miles. The year I went to both Alaska and Hawaii, I earned elite status and was upgraded to first class on almost every flight for the next year. Obviously, choosing the airline who has a hub in your city makes the most sense.

2) Get your preferred airline’s affiliate credit card. Here’s what I get for using my Skymiles American Express:

– I got 25,000 miles the first time I used the card. That’s a free domestic flight.

– I get double miles from (Why buy airfare through Travelocity or Expedia? All they do is list the airline’s own fares, sometimes with additional fees.)

– They often offer great promotions. I’m getting 5x the miles for my flights to San Diego, LA, and Key West because I bought them during the correct timeframe.

– Checked bags are free. Which means if two of you check bags once a year, you’ve recouped the annual fee. ($50/year, waived the first year.) That’s one bag per person for everyone in your party, too, not just your own suitcase.

– You earn miles on every purchase. If you’re a credit-card-averse person, you can do it the way I do: make the purchase with your American Express, then transfer the cash to Amex from your bank account. That way you owe no interest and don’t carry a balance.*

3) Check airfare obsessively, even multiple times a day. I saved $150 on my flight to San Diego just because I jumped on it at the right time. My preferred search engines are Bing (the fare predictor is pretty reliable) and Kayak (they seem to aggregate a few airlines you don’t see often on other sites). I’ve found that their search parameters make finding the right combination of flights much easier, and then you can just click through directly to the airline.

4) Sign up for every promotion airlines/credit cards offer, even if you don’t think you’ll take advantage of them. I’ve often accidentally qualified and gotten extra miles or cashback.

5) Get a luggage scale. I can’t believe we waited as long as we did to get one! Overage fees for bags are insane – often close to $100. Also, it really sucks to have to tear your bags apart and shove everything in a carry-on while you’re standing at check-in. Trust me on this.

If your bags are too heavy, go to the local post office and take advantage of their flat-rate shipping boxes. We packed those $15 boxes full of what was easily 30lb worth of souvenirs from Hawaii, and they were waiting for us when we got home. You’ll often find local shops offering this kind of shipping deal too, even in foreign countries.

6) Before redeeming frequent flier miles, calculate their value. It always changes. This article is old, but the lessons are correct: if the flight is cheap, you’re often better buying it and saving the miles for something more expensive, particularly if you will earn a lot of miles for flying that route. (You don’t earn miles on free flights, obviously.)

That’s really only valid if you fly regularly, though. If you don’t and have saved up enough for a free flight, you should probably use them if you can. Many airlines also offer the option to pay for a portion of the flight with miles, so that’s another situation where you need to evaluate the value of a mile.

7) Be flexible. The cheapest flights are always going to be the ones with more inconvenient times. Consider going a day earlier or coming back a day later. Most airlines’ sites let you search for a range of +/- 3 days, and the prices can vary a lot. If you’re a good plane-sleeper, they practically pay you to fly red-eyes. Consider flying to nearby airports and driving, too. (For example, it’s almost as easy to fly into Ft Lauderdale or Palm Beach as an alternative to Miami.)


1) Book your hotels through For every 10 nights you stay, you get a free night (valued at the average of the rates you paid over those 10 nights). I just got $154 off a booking in Key West. If you use the site regularly, they’ll upgrade you to their FiveStar service. I’m not sure exactly what that means, but the other day when I called the priority customer service number, I got to speak to a human right away.

The other benefits I like from while you do have to prepay for the booking, it’s almost always refundable following standard hotel policies (i.e. 24 hours prior). Most other sites only offer nonrefundable bookings if you want the best rate. Be sure to read the fine print on this, though, because each hotel is different. (I’ve booked close to 20 hotels with them, and they’ve all been fully refundable.) Also, they have a price guarantee: if you see your hotel offered on their site for a lower rate at any time, call or email them and they issue a refund for the difference. I got a refund within 24 hours.


1) For extra cash back, go through a deal site like Ebates. Every time I’m going to buy a ticket, book a hotel, or rent a car, I go through that site. Each Delta booking pays $1.50. Hotels and car rentals usually pay around 4%. It may not sound like much, but I’ve gotten $170 from Ebates just for clicking through to things I was purchasing anyway.

(And, yes, if you sign up via that link we each get $5. Win.)

2) Sign up for loyalty programs whenever you can. Airlines, hotels, cruise lines, and car rental companies all offer them. Who cares if they start sending you email? Unsubscribe. This is another case where I’ve found I’m accidentally collecting points or miles just by using those services. Many hotel programs let you convert your points to frequent flier miles, too.

3) Use Foursquare. Tourist destinations are really getting in on this, and many venues offer benefits. If you don’t want to check in all the time, just look up the place you’re going to and see if their special is worth it. In Vegas, we got 2-for-1 drinks more than once just for checking in at casinos. Foursquare can also be great for tips and recommendations.

4) READ REVIEWS. I can’t say this enough. That hotel’s website will make it look like the greatest paradise to ever exist, but reviews might tell you otherwise. And two reviews aren’t enough: find a volume of them, because one person’s crappy experience doesn’t necessarily mean you should write it off. I prefer TripAdvisor for this, because you can research any aspect of travel, including tours and activities.

Things to look for in particular: bedbugs (this is getting to be a big issue everywhere you go), cleanliness, customer service, and location. Those are all make-or-break items for me.


* I actually prefer cashback cards, because cash is almost always more valuable than any other benefit, be it miles or rewards. In certain cases it’s a better deal for me to use the Amex, though: double miles/promotions from Delta, and at Costco, because it’s the only card they accept. For any other major purchase, I tend to use a cashback card.

One comment on “how to get the most out of your travel dollars

  1. Pingback: how to get the most out of your travel dollars | Vacation Guide Site

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