How to Score a Paid First Class Vacation on Delta to the Caribbean, Costa Rica, or Mexico

May 2019
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With This Strategy, You Could Land a Free (or Even Paid) Vacation

Time and time again, our Stopover Loophole Strategy has proven to be a game-changer when it comes to scoring a great deal. We’ve covered this topic previously for both American and United, but now we want to highlight what’s possible with Delta.

As always, we recommend a broad approach when planning your next trip. The more open-minded you are, the better deal you’ll be able to find. With regards to Delta, our research shows that it’s possible to save hundreds of dollars on a round-trip Business Class ticket when you add a side destination to the Caribbean, Costa Rica, or Mexico.

Yes, that means that in some cases, you’re actually getting paid to take a vacation. And the best part is that this is possible with a number of common round-trip routes within the U.S. If you’re interested in scoring a great deal on your next vacation, keep reading…

But First, a Brief Overview of the Stopover Loophole Strategy

We call it the ‘Stopover Loophole Strategy’ but this idea certainly isn’t unique to the FCF platform. Our research team just happens to be great at spotting these deals.

Many of the best airlines have something called a ‘stopover allowance,’ where a stopover is defined as a planned stop of more than 4 hours (domestic) or 24 hours (international) between flight segments on a trip. But here’s the catch: these stopovers are sometimes allowed for free or a very small fee. And in some cases, your stopover could last for days—or weeks—if you wanted it to.

So, what does this mean? It means that you can book a ‘stopover’ in an awesome destination like the Caribbean, Costa Rica, or Mexico and get a free flight there! Or even better… sometimes it actually costs less money to add in a stopover. That’s when you’re getting paid to take a free vacation.

To recap, here’s what’s possible with this strategy:

  • You can actually get paid to book a side trip to an awesome destination (i.e. the total booking cost with the side trip added is cheaper than your original round-trip booking), or
  • You’ll be able to book a side trip for free (no additional cost to original round-trip booking), or
  • You pay a small fee to book the side trip (still considerably cheaper than booking a round-trip to the side trip destination by itself)

This strategy is ideal for:

  1. Leisure travelers who have the flexibility to add in a side trip when visiting friends or family across North America.
  2. Business travelers on a budget, but still want to sneak in a vacation on a business trip in North America.

How to Use Our Stopover Loophole Strategy to Get Amazing Business Class Travel Deals with Delta

Alright, it’s time to get into the specifics. Here are some examples of our Stopover Loophole Strategy in action:

Example 1:  New York (JFK) to Los Angeles

The chart below shows what our research found for the New York (JFK) to Los Angeles round-trip route with Delta. Here are a few of the highlights:

Adding a stopover in Cancun drops the total Business Class trip price from $1,669 to $1,220. That’s $449 cheaper—all for going on a vacation. Similar cost savings are possible throughout the Caribbean in places like Dominican Republic ($366 cheaper), Bahamas ($259 cheaper), Jamaica ($239 cheaper), and Sint Maarten ($211 cheaper).

In addition, you can get free side trips to San Jose del Cabo, Mexico City, and Puerto Vallarta.

Sample Savings With Delta Free Side Trips

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Example #2:  San francisco to New York (JFK)

Similar savings can be found on the San Francisco to New York round-trip route. Here, the best options for side trips are San Juan and Mexico City, where you’d save $341 or $388 respectively.

You can view our research results in the chart below:

Sample Savings With Delta Free Side Trips

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Example #3: Seattle to New York (JFK)

Another great round-trip route to consider for our Stopover Loophole Strategy is Seattle to New York. Here, the best options for side trips are San Jose, CR and Havana, where you’d save $444 or $287 respectively.

Sample Savings With Delta Free Side Trips

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tip of the iceberg

Our research has found great side trip options for routes like New York to Portland, Seattle to Boston, Atlanta to Los Angeles, and much more.

The key thing to remember is that you should always check the stopover options if you want to book a round-trip flight within in the US, even if you weren’t originally planning on taking a side trip. You never know what great deal is hiding right around the corner. This strategy makes it easier than ever to book your next vacation at a fraction of the cost.

[["Normal Trip","Normal Premium Fare R\/T","Side Trip City","New Premium Fare w\/Side Trip","Free Side-Trip Savings"],["New York (JFK) - Los Angeles"," $1,669","Nassau"," $1,410"," $259"],["#rowspan#","#rowspan#","Santo Domingo"," $1,354"," $315"],["#rowspan#","#rowspan#","Santiago (STI)"," $1,303"," $366"],["#rowspan#","#rowspan#","Kingston"," $1,430"," $239"],["#rowspan#","#rowspan#","Sint Maarten"," $1,458"," $211"],["#rowspan#","#rowspan#","Cancun"," $1,220"," $449"],["#rowspan#","#rowspan#","San Jose del Cabo"," $1,350"," $319"],["#rowspan#","#rowspan#","Puerto Vallarta"," $1,510"," $159"],["#rowspan#","#rowspan#","Punta Cana"," $1,480 "," $189"],["#rowspan#","#rowspan#","Mexico City"," $1,400 "," $269"]]
<small>* Fare valid at time of publishing and will vary based on advance purchase and many other factors. Fares displayed are commonly seen when booking a month or so in advance, although the strategy can often work on short-notice.</small>
[["Normal Trip","Normal Premium Fare R\/T","Side Trip City","New Premium Fare w\/Side Trip","Free Side-Trip Savings"],["San Francisco - New York (JFK)"," $1,717","San Jos\u00e9 del Cabo"," $1,488"," $229"],["#rowspan#","#rowspan#","Mexico City"," $1,329"," $388"],["#rowspan#","#rowspan#","San Jose Costa Rica"," $1,615"," $102"],["#rowspan#","#rowspan#","San Juan"," $1,376"," $341"],["#rowspan#","#rowspan#","Guadalajara"," $1,397"," $320"],["#rowspan#","#rowspan#","Antigua"," $1,511"," $206"],["#rowspan#","#rowspan#","Grand Cayman"," $1,521"," $196"]]
<small>* Fare valid at time of publishing and will vary based on advance purchase and many other factors. Fares displayed are commonly seen when booking a month or so in advance, although the strategy can often work on short-notice.</small>
[["Normal Trip","Normal Premium Fare R\/T","Side Trip City","New Premium Fare w\/Side Trip","Free Side-Trip Savings"],["Seattle - New York (JFK)"," $1,607","Havana"," $1,320"," $287"],["#rowspan#","#rowspan#","San Juan"," $1,322"," $285"],["#rowspan#","#rowspan#","San Jose Cosa Rica"," $1,163"," $444"],["#rowspan#","#rowspan#","Cancun"," $1,327"," $280"],["#rowspan#","#rowspan#","San Jose del Cabo"," $1,462"," $145"],["#rowspan#","#rowspan#","Mexico City"," $1,460"," $147"],["#rowspan#","#rowspan#","Santo Domingo"," $1,518"," $89"],["#rowspan#","#rowspan#","Kingston"," $1,582 "," $25"]]
<small>* Fare valid at time of publishing and will vary based on advance purchase and many other factors. Fares displayed are commonly seen when booking a month or so in advance, although the strategy can often work on short-notice.</small>