78% Off Christmas Vacation in Jamaica

78% Off Christmas Vacation in Jamaica


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Image courtesy: Tomash Devenishek

Trip Information

Reader Elena found a 30% off deal for a Christmas vacation in Jamaica at an all-inclusive resort. To take advantage of this, she needs to find flights for four total passengers from Minneapolis. She’s looking to travel from December 20th until the 28th. She has one or two days of flexibility on either side of these dates.

Current Program Status

Elena presently has 55,000 United miles in her own program and 55,000 available in another passenger’s account. Three total passengers, including Elena, also have US Airways mileage balances of 35,000 each. They’re willing to consider applying for a new travel credit card if it could help them earn any miles needed for this trip quickly.

Our Take

As is always the case with a larger party, we’ll make keeping the whole family together our first priority in creating a trip. Only if there’s absolutely no way forward do I ever start considering splitting families into two traveling parties. That won’t be necessary today.

However, traveling to a tropical vacation destination at Christmastime on miles and points is not easy. This is naturally one of the most popular times of the year to travel, and that means people often book up to a year in advance. Since a lot of availability has already been eaten away on the most straightforward award routes, we’ll have to be creative in finding a solution. Let’s dive in!

Checking In On United

Of course, since Elena has a stack of miles with United and US Airways ready to go, they are our first choices in putting this trip together. United allows for one-way trips to be booked, so even if there’s only availability in one direction, we should still be able to take advantage of their program.

US Air, on the other hand, requires award tickets be booked as roundtrips. That means if we can’t find roundtrip availability, US Air’s program won’t be useful to us. In addition, the airline charges a $35 fee on all award bookings – even those placed online!

These two rules are major reasons why I’m looking forward to US Air being rolled into American, which allows for one-ways and only charges booking fees if you phone in for help. It’s already possible to book US Air flights using AAdvantage miles and vice versa, but US Air mileage holders will be locked into US Air’s ruleset until the option to convert Dividend Miles into AAdvantage miles comes available.

Let’s first check availability with United. Here’s a look at open dates for four passengers from Minneapolis to Montego Bay:

Yikes! As you can see, there’s no Saver Economy availability remotely close to the dates Elena’s looking to travel. Even searching for just two passengers doesn’t open up very many dates in December, and none around Elena’s travel time.

Let’s check the way back:

Thankfully, you can see our options are much more open for the flight home. Flights departing on 12/28 would actually require an overnight stop in Houston, so our best bet is this itinerary back on 12/27:

In total, four passengers on this flight will take 70,000 miles and $238.04 in taxes and fees, a huge savings over the cash price:

That’s all well and good, but since United can’t get us there – only bring us back – we’d better check and see if US Air has any roundtrip solutions available.

US Air’s Disappointing Results

Here’s a look at award availability via US Air:

The lightest blue dates indicate availability at 17,500 miles each way. Moderately blue dates require 30,000 miles each way. Dark blue dates take 40,000 miles each way.

As you can see, some light blue, 17,500 mile dates exist for the flight home, but availability on the way there is terrible, requiring 40,000 miles per person for half the trip. Making matters worse, remember that US Air awards must be booked as roundtrips. That means even a best-case scenario of leaving on the 18th and returning on the 25th – not in line with Elena’s dates – would take 47,500 miles per person, which is more than are in any one account Elena has to work with.

Adding insult to injury, total fees of $144 per person for a roundtrip would apply to this itinerary, nearly triple what United’s charging for just the ride home.

I did some digging to see if perhaps it wasn’t the flight to Montego Bay, but one of the connecting flights from Minneapolis, that could be causing US Air availability to be so poor. I tried searches from each American and US Air hub, on the logic that perhaps a cheap cash ticket to that hub would allow for a better award redemption.

My search was largely fruitless, but did yield one lead: flights from Miami to Montego Bay were available at Saver Economy levels. While 17,500 miles for such a short flight makes little sense, the fact that space was available leads us to a solution in another program.

Avios to the Rescue

Longtime readers are surely familiar with Avios, British Airways’ award miles program. While most programs, including United and US Air, base their redemption costs on what region you’re leaving from and where you’re arriving, British Airways bases their program on distance flown. That means short and typically expensive flights can be excellent Avios redemption opportunities.

Sure enough, Montego Bay is 524 miles from Miami. That means the direct flights offered by British Airways partner American Airlines can be had for just 4,500 Avios each way.

As it turns out, there are two flights available on December 21st with precisely four award seats each available to Avios bookers:

At 4,500 Avios each, that’s a total of 18,000 Avios for four passengers, and taxes/fees of $256 in total.

However, a number of other pricing options are also available for this flight. For $160 more, it’s possible to knock down the number of Avios required to 10,000. This might be important depending on how Elena procures her Avios.

Because availability is so constrained, this is a rare case where we might recommend purchasing Avios if necessary. If Elena has an Ultimate Rewards card – such as Chase Ink or Sapphire Preferred – or a Membership Rewards card with American Express – then she can easily transfer these points to British Airways instantly at a 1:1 rate. She could also transfer points from an SPG American Express.

We’ll assume she doesn’t have any of these at the moment. The best deal would be to take the pricing option requiring just 10,000 Avios. These may be purchased from British Airways for a total of $300.

On top of the taxes and fees of $416, that would mean a total cost for the jump from Miami to Montego Bay of $716. That may sound expensive, but compare it to the cash cost for the same flight of $1,034:

By being willing to jump through the hoop of purchasing a few Avios and then booking this flight through British Airways (see our guide on how to do this), Elena can save about $318 versus purchasing the same ticket outright.

Of course, we still need to get her to Miami in the first place.

Southwest to Miami

One points-based option for this would be to rack up some Rapid Rewards points with Southwest, fly into Fort Lauderdale from Minneapolis, then take the Tri-Rail south for a few dollars per person to Miami International.

Southwest’s booking window is only presently open through October, but let’s take a look at the cost of flights from Minneapolis to Fort Lauderdale for that month:

As you can see, prices of 10,028 points per passenger are quite common. I’d expect these rates to hold true once the December calendar opens up.

Elena could earn these miles quickly with a Sapphire Preferred card, which comes with a 40,000 Ultimate Rewards Points bonus after $3,000 in spending. As we mentioned a moment ago, Ultimate Rewards points can transfer to a number of airlines and hotel programs at a 1:1 rate. That includes not only British Airways but also Southwest.

Looking more specifically at flight schedules from Minneapolis to Fort Lauderdale, we see this flight as the best option:

Its 1:55PM arrival time leaves plenty of room to transfer to Miami International for the American flight to Montego Bay that leaves at 6:50PM. The tickets from Minneapolis to Fort Lauderdale come in at just $2.50 each, enough to cover the mandatory security fee.

Wrapping Up

This itinerary is more complicated than we’d like it to be, and it’s possible that award availability will actually improve a few months down the road and yield a better option. However, given Elena’s looking to go at the very height of holiday travel season, we probably wouldn’t wait around. She’s still able to use her United miles to save a pile of money on the flight home and is able to reap a fair discount on the flight out by simply purchasing and using Avios instead of buying a cash ticket directly.

Let’s say Elena were to purchase the Southwest flights for roughly $176 per person instead of use Rapid Rewards points. In that case, she’d be looking at a total of $704 to get to the Miami area and then $716 to go from Miami to Montego Bay, which combines to $1,420. Compare this to the best cash route direct from Minneapolis to Montego Bay for the same day, at $1,619.80, and there’d still be savings to be had.

By using newly minted points to cover the flight from Minneapolis to Fort Lauderdale, she can knock more than $700 off the cost of the trip. If she has just 10,000 Avios available, or can mint some by converting points from another program like Ultimate Rewards, Membership Rewards or SPG, she can knock another $300 off the cost. We’ll assume for safety’s sake she purchases the Avios and books the flight from Miami to Montego Bay now, but there’s no reason why Southwest points can’t be earned well in advance of booking the flights from Minneapolis to Fort Lauderdale, which aren’t even available for ticketing yet.

This trip’s a good example of how points programs can be used to save both big money – such as on the United flight on the way home – and small money – by outright purchasing Avios to cover an expensive cash flight. When an award calendar looks barren, don’t look at it as the end of the road, but rather the beginning of a puzzle that, with a bit of clever thinking, can still save you a fair amount over the cash price. For us, a mere 72% off might seem like a bad day, but that only goes to show just how powerful points and miles can be in action!

Trip Component Cash Price Points + Cash Savings
Southwest + British Airways Avios Awards: Minneapolis to Fort Lauderdale on Southwest & Miami to Montego Bay on American • Economy 4 Passengers $1,619.80 Total (Booked as one trip on American) 40,112 Rapid Rewards Points + $10 Taxes/Fees Total + $300 of Purchased Avios Each + $416 Taxes/Fees Total $893.80
United Award: Montego Bay to Minneapolis • Economy 4 Passengers $1,456.04 Total (United) 70,000 United Miles + $238.04 Taxes/Fees Total $1,218.00
Total: $3,075.84 40,112 Rapid Rewards Points + 70,000 United Miles + $300 of Avios + $548.04 Taxes/Fees $2,227.80 (72% Off)

Happy travels!

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About PointsAway
Casey Ayers is a consultant and entrepreneur with a passion for travel. After amassing enough miles and points to travel anywhere in the world for almost free in less than six months, he developed PointsAway as a way to help others make travel dreams big and small come true.
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