Earn more miles (many more) for any flight, any hotel, any cruise

OK, this doesn’t really work for “any” flight, hotel, or cruise, but it should work for most…  Read on… 

A few days ago, a reader named Andrew told me that he had booked a trip via Sears Vacations and had paid for it with two Sears’ gift cards.  Whoa, I didn’t know you could do that!  I had looked into it a couple of years ago, but it didn’t seem to work at that time.  The website didn’t offer a way to pay with a gift card, and when I called Sears Vacations back then I was told that gift cards weren’t accepted.  At the time, I let it go at that.  Maybe I should have tried harder.

When Andrew told me about his success, I jumped online immediately.  I had a flight that needed to be booked right away, so I figured that this would be a great test.  Using the Sears Vacations website, I searched for the flight in question.  It priced $10 more than competing sites.  Since this was a $450 flight, the $10 booking fee amounted to just over 2%.  For the sake of using my ready supply of Sears’ gift cards, I decided that was fair.  I’d be less likely to go for it if I was booking a very cheap flight since the fee would then be a much larger percent of the total.

I tried to buy the flight online, but there was no obvious place to put my gift card information.  Rats.  I had to call.

Success… Sort of

I called Sears’ Vacations and the phone agent asked how she could delight me (seriously).  I told the agent the situation: I had found a flight online, but wanted to pay by gift card.  She was unfazed by the request.  I fed her the flight info and soon enough she found the right flight.  I gave her all of the info she asked for and then gave her the gift card number and PIN for payment.  She then put me on hold for about 20 minutes.  Finally she returned and said the flight was booked and I should receive an email confirmation shortly.  That wasn’t too bad, but the 20 minute delay made me glad that I had a single gift card large enough for the whole order.  What if I had asked her to split payments across multiple gift cards like Andrew had done?  How long would that have taken?

The confirmation email arrived in about an hour (not my definition of “shortly”, but OK).  Unfortunately, I discovered that my name was incorrect on the reservation.  Ugh.  Time for bed.  I would deal with this in the morning.

The long fix

In the morning I called the support number listed on my itinerary.  “Thanks for calling Travelocity” a voice said.  Interesting.  I told the agent the problem.  He said that I could cancel the ticket for a refund or pay Delta’s $50 name change fee.  Uh, what?  I certainly wasn’t going to pay $50, but I was also hesitant to ask for a refund.  Where would the refund go?  My itinerary claimed that the ticket was paid for with an American Express card ending in a number that didn’t match my gift card.  Thank you, no, “I’ll call Sears Vacations,” I said.

I called Sears Vacations, described my problem, and was transferred to a ticketing specialist.  And there I learned that the ticketing specialist department would open at 9 a.m. Central Time, which was about an hour away.  I would have to wait.

I called later and again was transferred to the ticketing department, but this time they were open for business.  A very friendly and capable agent tried first to simply get my name changed on the existing reservation, but without success. He wasn’t any more interested than I was in the dicey route of trying to refund a gift card purchase, so he put me on hold for a long time while he investigated options.  Finally, he came back with a simple suggestion: he would rebook the flight and simultaneously cancel the old flight and credit the funds from that flight towards the new one.  Lucky for me, this was within the 24 hour cancellation window and the flight I wanted hadn’t changed in price.  Soon enough, it was all taken care of.  I had successfully booked a flight and paid with a Sears gift card!

Hotels, Cruises, etc.

Sears Vacations offers the usual assortment of stuff: flights, hotels, cruises, car rentals, etc.  Andrew booked a resort stay.  I booked a flight.  It seems reasonable to assume that everything available on their website can be paid for with gift cards.

Prices?

I took a quick look at hotel prices on the Sears’ Vacations website and found that prices were quite a bit higher than the same properties listed on Kayak.  The website claims, though, to have a Best Price Guarantee.  The general idea is that, after you book with Sears Vacations, you can contact them within 24 hours to make a claim.  If verified, they’ll refund the difference to you.  What if you paid with a gift card?  How would the refund be processed?  I don’t know.  I suspect that the first reader to try this will have enough material for his/her own blog post on the subject.  Sure it’s possible that the credit will automatically go back to the original gift card…  Lot’s of things are possible.

Trip protection

One downside to paying for trips with gift cards is that you usually lose the trip protections automatically offered by many credit cards.  As I pointed out recently, though, Chase has revised most of their credit card benefits guides.  Once the new benefits are in place for each card, Chase will offer many benefits even if you pay for only a part of the trip with your card.  One notable exception is the rental car collision damage waiver which still requires you to pay entirely with your credit card for coverage.  See “Partial payment, full trip coverage” for full details.  The point here is that it makes sense to pay for at least a small part of your Sears Vacation with a Chase credit card.  I wish that had occurred to me before I had paid for my flight!

Gift cards trump points & miles for business trips

One advantage of this gift card approach is that you’ll get a receipt showing the total price paid.  When traveling for business, you might need this receipt to get reimbursed or to prove the expense on your taxes.  Either way, it can be tricky to do the same if you pay for a trip with miles and points.

Miles, points, and savings

I have written many times about various ways to earn points, miles, or cash back when buying Sears gift cards.  See, for example, “Best options for buying merchant gift cards.”  Rather than extend this already long post, I’ll follow up soon with a number of examples.  In the meantime, don’t forget that through October 20th Lands’ End is offering 10X through the AAdvantage eShopping portal.  And, Lands’ End gift cards work anywhere that Sears’ gift cards are accepted…

Personally, I bought about $3,000 worth of Sears’ gift cards when Sears offered 16 miles per dollar through the MileagePlus Shopping portal.  I paid for half of the gift cards with my Freedom card and half with my Discover card so as to earn each card’s quarterly 5X bonus.  If all of the expected portal points post (it often takes 3 weeks or more, so I don’t know yet), then I will have earned 21 points per dollar on those purchases.  So, I can say that my $450 flight will earn over 9000 points (7200 United miles, and 2250 Ultimate Rewards points, or $22.50 in Discover Cash).  And, since this is a paid flight, not an award flight, I’ll earn miles the old fashioned way too – by flying.  Oh yeah, and I earned lots of Plink points too…

Bottom line

There are many ways to get bonus points or savings when buying Sears’ gift cards.  And, Sears Vacations can be a great way to make use of those cards.  I just wish they allowed gift cards to be entered in for payment online.  Not only does it take longer to call to make a booking, but it also makes errors more likely. 

Want to learn more about miles and points? Subscribe to email updates or check out our podcast on your favorite podcast platform.