Upgrade Masterclass: Use FCF’s Stopover Loophole Strategy to Get 51% Off Within the U.S., Caribbean, and Mexico. Part 1

March 2025
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Get two trips — plus two side trips — for the price of one round-trip

Imagine you’re headed to Miami for business or leisure, but instead of just visiting Miami, the airline ticket you have includes a stop in the Caribbean – for a few days or more — at no extra cost.

In fact, with FCF’s Stopover Loophole Strategy (SLS), you could end up paying less than you would for a simple round-trip ticket.

Or suppose you’re headed to Los Angeles, but instead of just going to California, your ticket includes a free — or less than free — trip to Mexico to start or end your trip.

Let’s delve into my SLS, a travel strategy that turns ordinary trips into extraordinary experiences without breaking the bank.

In The Upgrade Process, we always start with our baseline. It’s our starting point. Starting points, assumptions, or default states shape everything we experience, perceive, and choose. It’s like a lens we don’t always notice we’re looking through, yet it colors the whole picture.

Let’s start with a snapshot of how good this strategy can be for our initial perspective. Then let’s look at who might desire to use the strategy, the range of potential itinerary options, and the questions to consider for making a decision.

SLS Sample Savings

Los Angeles-Miami round-trip is currently going for $1,942 in Business Class (for non-red-eye or 6:00 AM flights) on American Airlines. Add on San Juan, Puerto Rico, to your trip, and the fare can drop to $960 — that’s $982, or 51% less, plus the bonus Caribbean win.

Typical American Fare on AA.com Los Angeles - Miami Round-Trip
Typical American Fare on AA.com Los Angeles - Miami - San Juan - Los Angeles Using FCF’s Stopover Loophole Strategy (SLS)

Full disclosure: Not all options are this good; the strategy is hit and miss. And it works better with American at the moment. But there are many options that can get you a free or cheap upgrade. More analysis on the options in a minute.

Already Flying Business Class?
Here’s Your SLS Perspective:

Trip Type Example Itinerary Business Class
Normal Round-Trip Los Angeles - Miami (Stop) $1,942
Loophole Strategy (SLS) Los Angeles - Miami (Stop) Miami - San Juan, PR (Stop) San Juan, PR Los Angeles $960
The SLS Difference COST SAVINGS $982 / 51% LESS
BENEFIT Save $982 + Flight to Caribbean

Cramped in Coach Class?
Here’s Your SLS Upgrade Perspective:

Normal Los Angeles - Miami Round-Trip Scenario
Los Angeles - Miami (Stop) Miami - Los Angeles  Coach $477
Business $1,942
Free Elite Upgrade Odds Almost Nil
Cost to Upgrade Trip $1,465
FCF's SLS Difference
Los Angeles - Miami (Stop) Miami - San Juan, PR (Stop) San Juan, PR-Los Angeles SLS Business Class $961
Normal R/T Coach Class $477
Cost to Upgrade LA-Miami Trip $484
Upgrade Cost Savings SLS vs Normal $981 Cheaper*
Additional SLS Benefit Free Flight to the Caribbean

*Bonus: Earn More Elite Credit and Miles with SLS Extra Flights

Considering Premium Economy? Here’s Your SLS Upgrade Perspective:

Normal Round-Trip Scenario
Los Angeles - Miami (Stop) Miami - Los Angeles Premium Economy $645
Business $1,942
Free Elite Upgrade Odds Almost Nil
Cost to Upgrade Trip $1,297
FCF's SLS Difference
Los Angeles - Miami (Stop) Miami - San Juan, PR (Stop) San Juan, PR-Los Angeles SLS Business Class $961
Normal R/T Premium Economy $645
Cost to Upgrade LA-Miami Trip from Prem Econ to SLS Business Class $316
Upgrade Cost Savings SLS vs Normal $981 Cheaper**
Additional SLS Benefit Free Flight to the Caribbean

51% savings?
That means two trips — plus two side trips — for the price of one round-trip.

Baseline: Upgrade Mindset Pro-Tip

What’s your baseline? Just like our lives aren’t always just shaped by big choices, but more impacted by the quiet, often unnoticed foundation we’re already working from, neither are our travel choices.

Your baseline frames your life. It’s a lens you don’t always notice you’re looking through, yet it colors the whole picture. It’s not just “you are what you eat” — it’s “you see what you stand on.”

My desire is that after reading this special report, you’ll shift your thinking and the baseline from which you make travel (and any other upgrade) decisions will improve. Exploring new options can crack open otherwise hidden desires.

Now that we have a deeper understanding of the FCF Stopover Loophole Strategy baseline, let’s build on the potential and perspective.

The strategy doesn’t work everywhere all the time. Within North American, it works occasionally with Delta and United at the moment, and best in conjunction with American’s hubs – Charlotte, Chicago, Dallas-Fort Worth, Los Angeles, Miami, New York, Philadelphia, Phoenix, and Washington, D.C. – as origins, destinations, or side trips. More on the many options in a moment.

Why does SLS work?

After publishing the longest running newsletter in the history of the air travel industry, I’d love to be smug and tell you I knew exactly why, and I kinda do. It essentially has to do with complex airline pricing structures, and how they sometimes work with stopovers, and sometimes don’t.

In the world of air travel, a stopover is typically a layover lasting more than four hours domestically, often stretching into days or weeks for LESS or little to no additional cost. With SLS, you’re not just traveling from point A to point B, with a stop of a few hours, however. You’re turning a layover into a multi-destination feast.

That’s because the stopover can be turned into a vacation if you’re on a business trip or a second vacation if you’re already traveling for pleasure or visiting grandma.

Now that we have an improved, upgraded starting point, let’s look at the desires for various types of travelers and scenarios.

UPGRADE PROCESS Step #2: Desires

What do you want?

Universal Upgrade Process–Pro-Tip: While the process has five steps, in reality, you don’t always follow them sequentially. For example, an opportunity might just appear out of left field. Take the SLS for example in this special report's baseline. When you start with an opportunity, or an option, that’s great, just go back to step 1, or at least to step 2 (Desires), and ask yourself upgrade or improvement questions. Let’s give it a try now.

Can you identify with any of the following?

Who Can Benefit from SLS?

Traveler Type This Your Baseline? Desire This?
Travel for Business Come right home after a meeting or conference AND faced with a Business/First Class fare that's not cheap? Could you use a little more rest and relaxation or adventure away? AND/OR Would you travel more for business if you could expense vacation flights?
Travel for Leisure Do you have a trip in mind to visit a friend or grandma for her birthday? Wouldn't mind hitting Jamaica for a few days or longer while you're already out and about AND save money in the process?
Fly in Coach or Premium Economy Business Class is beyond the budget? Cheaper upgrades Looking for extra experiences?
Elite Status Flyer Never get free upgrades? Break free from fake free upgrade promises AND/OR earn more elite credit for the extra segments, miles, and class of service bonus?
Loyalty-Free Flyer Always fly with the airline with the best routing/schedule or deal? The world evermore is your oyster!
Already Have a Flight Booked Open to saving money AND/OR getting a cheap, free, or less than free cool bonus destination AND forgot or don't know that you can exchange the ticket you already have bought (without fees or penalty) for a new ticket? A cheaper trip AND/OR a bonus side trip AND/OR earn more miles or elite credit?

Before you commit to a desire, pause to explore your desire options. What you want on the surface — a trip, perhaps — might mask a deeper longing: to rest, to wander, to break free. The more options you consider, the more you uncover about what truly moves you. How often have you chased a want only to find, through exploration, it wasn’t what you originally thought—or you stumbled upon something better later on?

Where does SLS work best within North America?

American

Works best with low-cost add-on destinations:

  • Cancun, Corn Islands, La Romana, Managua, Mexico City, Montego Bay, Nassau, Puerto Vallarta, Rincon, San Juan, U.S Virgin Islands
  • When ordinarily flying TO American’s hubs: Miami, Charlotte, Dallas, Phoenix
  • With transcons to low-cost add-on destinations:
    • From Los Angeles and San Francisco to New York and Miami
    • From New York to San Francisco or Los Angeles

Delta

Works best with lowcost add-on destinations:

  • Cancun, Punta Cana, Montego Bay, San Juan
  • When ordinarily flying TO Delta’s hubs: Los Angeles (LAX) and Atlanta (ATL) to destinations like New York (JFK) and Atlanta (ATL)
  • With transcons to low-cost add-on destinations:
    • From Los Angeles to New York (JFK) and Atlanta
    • From Atlanta to Los Angeles

United

Works best with low-cost add-on destinations:

  • Cancun, Mexico City, Punta Cana, La Romana, Montego Bay, Guatemala City
  • When ordinarily flying TO United’s hubs: Los Angeles (LAX) and San Francisco (SFO) to destinations like Boston (BOS) and New York (JFK)
  • With transcons to low-cost add-on destinations:
    • From Los Angeles to Boston and New York (JFK)
    • From San Francisco to Boston

Samples of Where the SLS Works Best – To Miami on American

Your Home Airport BASELINE: Normal Business Class Fare Miami R/T Your DESIRE Add-On OPTIONS: with SLS SLS Fare Bonus City
Los Angeles $1,962
More for Less
San Juan, PR $957 -$1,005
Rincon, PR $897 -$1,065
Cancun $1,762 -$200
Nassau $1,803 -$159
Mexico City $1,816 -$146
La Romana $1,725 -$237
Montego Bay $1,607 -$355
St. Thomas $1,029 -$933
San Francisco $1,980 San Juan, PR $1,042 -$938
La Romana $1,769 -$211
Monterrey, Mexico $1,760 -$220
Philadelphia $1,030 San Juan, PR $994 -$36
Antigua, Guatemala $1,040 $10

Other Sample American Deals

Home Airport Originally Planned Destination Normal Business Class Add-On Option: SLS Biz Class Fare Bonus SLS City
New York/JFK San Francisco $1,980 San Juan, PR $1,456 -$524
Phoenix
$1,560
Mexico City $1,338 -$222
San Juan, PR $1,366 -$194
Cancun $1,439 -$121
Nassau $1,482 -$78
Dallas
$1,190
Montego Bay $944 -$246
Rincon $997 -$193
Nassau $1,051 -$139
San Francisco New York/JFK $1,870 Nassau $1,769

-$101

Puerto Vallera $1,776

-$94

Nassau $1,837

-$33

Los Angeles

$2,200 San Juan, PR $1,689

-$511

Cancun $1,487 -$713
Charlotte $1,660 San Jose Del Cabo $898

-$762

Belize $985

-$675

Cancun $1,285

-$375

San Jose Del Cabo $1,588

-$72

Belize $1,686

$26

Atlanta $1,930 Cancun $1,400 -$530
Punta Cana $1,413

-$517

Montego Bay $1,692

-$238

San Juan, PR $1,841

-$89

Transcon Opportunities On American

Route Normal Business Class Round Trip Add-On Option: with SLS Side Trip Cost Bonus SLC City
New York/JFK - SFO $1,980 San Juan, PR $1,456 -$524
Los Angeles - New York/JFK $2,200 San Juan, PR $1,487 -$713
New York/JFK - Phoenix $1,560 Mexico City $1,338 -$713
New York/JFK - Phoenix $1,560 Cancun $1,439 -$121
San Francisco - New York/JFK $1,870 La Romana $1,769 -$101
San Francisco - Philadelphia $1,590 San Juan, PR $1,585 -$5

Delta Deals

Home Airport Originally Planned Destination Normal Business Class Round Trip Add-On Option: with SLS SLS Fare Bonus SLS City

Los Angeles
New York/JFK $2,200 Cancun $1,487 -$713
Atlanta $1,930 Cancun $1,400 -$530
Nassau $1,413 -$517
San Juan, PR $1,692 -$238
Cancun $1,841 -$89

United Deals

Home Airport Originally Planned Destination Normal Business Class Round Trip Add-On Option: with SLS SLS Fare Bonus SLS City
Los Angeles New York/JFK $2,200 Guatemala City $2,171 -$29
Boston $1,613 Cancun $1,460 -$153
Mexico City $1,501 -$112
Punta Cana $1,520 -$93
La Romana $1,586 -$27
Montego Bay $1,594 -$19
San Francisco $1,464 San Juan, PR $1,431 -$33

Cracking the Elite Curse & The Upgrade Mindset

Your mindset on airline loyalty elite status programs frame your travel life. It filters what you want and what you think you can have. Elite status expectations shape much of what many experience, perceive, and choose in the world of flying.

Be honest with yourself. The loyalty you’re giving to American, Delta, and United isn’t being reciprocated, is it? Elite travelers know the drill too well — those glossy benefits dangling free upgrades like a carrot on a stick, but the line’s so long you’re left chewing on coach.

It’s a promise whispered by a con artist, or a lottery ticket that never cashes in. You’re stuck in the crucible: pay for First Class and feel robbed of your status, or roll the dice in economy and curse the odds.

Different airlines offer different deals and schedules with the Stopover Loophole Strategy - so locking yourself into loyalty to one airline locks yourself out of options. That’s as true with SLS as any other. That’s why I’ve been advocating for loyalty-free agency for decades.

Closing Arguments

You’ve already done the grunt work: packed the suitcase, lined up the dog sitter, done all the preparations to leave home. So why let that effort sputter out on a one-stop trip when you could tack on a detour that turns a routine trip into a jackpot?

SLS is the poster child for getting more for less. Have to visit a client in Dallas? Why not add on the Miami Grand Prix — and perhaps write off the flight? Facing a ridiculously high First Class fare? Why not cut it in half — in effect having the airlines pay for your trip to the beach. Your hotel and dinner can be financed by the airlines if you’re opportunistic.

If you did this as a lifestyle, you’d go to twice as many places, your experience wealth would double. Best of all, with The Upgrade Process and Mindset, it can even cost you less.

Stay tuned for next month’s SLS Part 2.

Until then, see you up front.

P.S. A friendly reminder to provide feedback on our weaving in The Universal Upgrade Process and Mindset into the travel strategy. We’re about to re-launch The Upgrade Formula and would love your input along the way.

[["Trip Type","Example Itinerary","Business Class","#colspan#"],["Normal Round-Trip","Los Angeles - Miami (Stop)","$1,942","#colspan#"],["FCF's Stopover\nLoophole Strategy (SLS)","Los Angeles - Miami (Stop)\nMiami - San Juan, PR (Stop)\nSan Juan, PR Los Angeles","$960","#colspan#"],["\n<big><strong>The SLS Difference</strong></big>","#colspan#","COST SAVINGS","$982 / 51% LESS"],["#rowspan#","#rowspan#","BENEFIT","Save $982 + Flight to Caribbean"]]
[["<big>Normal Los Angeles - Miami Round-Trip Scenario</big>","#colspan#","#colspan#"],["\n\n\n<strong>Los Angeles - Miami (Stop)\nMiami - Los Angeles</strong>","Coach","$477"],["#rowspan#","Business","$1,942"],["#rowspan#","Free Elite Upgrade Odds","Almost Nil"],["<strong>Cost to Upgrade Trip</strong>","#colspan#","<strong>$1,465</strong>"]]
[["<big>FCF's SLS Difference</big>","#colspan#","#colspan#"],["<strong>Los Angeles - Miami (Stop)\nMiami - San Juan, PR (Stop)\nSan Juan, PR-Los Angeles</strong>","SLS Business Class","$961"],["#rowspan#","Normal R/T Coach Class","$477"],["<strong>Cost to Upgrade LA-Miami Trip</strong>","#colspan#","<strong>$484</strong>"],["<strong>Upgrade Cost Savings SLS vs Normal</strong>","#colspan#","$981 Cheaper*"],["<strong>Additional SLS Benefit</strong>","#colspan#","Free Flight to the Caribbean"]]
<small>*Bonus: Earn More Elite Credit and Miles with SLS Extra Flights</small>
[["<big>Normal Round-Trip Scenario</big>","#colspan#","#colspan#"],["\n\n\n<strong>Los Angeles - Miami (Stop)\nMiami - Los Angeles</strong>","Premium Economy","$645"],["#rowspan#","Business","$1,942"],["#rowspan#","Free Elite Upgrade Odds","Almost Nil"],["<strong>Cost to Upgrade Trip</strong>","#colspan#","<strong>$1,297</strong>"]]
[["<big>FCF's SLS Difference</big>","#colspan#","#colspan#"],["<strong>Los Angeles - Miami (Stop)\nMiami - San Juan, PR (Stop)\nSan Juan, PR-Los Angeles</strong>","SLS Business Class","$961"],["#rowspan#","Normal R/T Premium Economy","$645"],["<strong>Cost to Upgrade LA-Miami Trip from Prem Econ to SLS Business Class</strong>","#colspan#","$316"],["<strong>Upgrade Cost Savings SLS vs Normal</strong>","#colspan#","$981 Cheaper**"],["<strong>Additional SLS Benefit</strong>","#colspan#","Free Flight to the Caribbean"]]
<small>*Bonus: Earn More Elite Miles and Credit with SLS Extra Flights</small>
[["Traveler Type","This Your Baseline?","Desire This?"],["\n\n<strong>Travel for Business</strong>","\nCome right home after a meeting or conference\n<strong>AND</strong>\nfaced with a Business/First Class fare that's not cheap?","Could you use a little more rest and relaxation\nor adventure away?\n<strong>AND/OR</strong>\nWould you travel more for business if you\ncould expense vacation flights?"],["\n<strong>Travel for Leisure</strong>","\nDo you have a trip in mind to visit a friend\nor grandma for her birthday?","Wouldn't mind hitting Jamaica for a few days\nor longer while you're already out and about\n<strong>AND</strong>\nsave money in the process?"],["\n<strong>Fly in Coach or Premium Economy</strong>","\nBusiness Class is beyond the budget?","Cheaper upgrades\n<strong>AND/OR</strong>\nLooking for extra experiences?"],["\n<strong>Elite Status Flyer</strong>","\nNever get free upgrades?","Break free from fake free upgrade promises\n<strong>AND/OR</strong>\nearn more elite credit for the extra segments, \nmiles, and class of service bonus?"],["<strong>Loyalty-Free Flyer</strong>","Always fly with the airline with the best routing/schedule or deal?","The world evermore is your oyster!"],["\n\n<strong>Already Have a Flight Booked</strong>","Open to saving money\n<strong>AND/OR</strong>\ngetting a cheap, free, or less than free cool bonus destination\n<strong>AND</strong>\n<strong>forgot or don't know</strong> that you can exchange the ticket\nyou already have bought (without fees or penalty) for a new ticket?","A cheaper trip\n<strong>AND/OR</strong>\na bonus side trip\n<strong>AND/OR</strong>\nearn more miles or elite credit?"]]
[["Your Home Airport","BASELINE:\nNormal Business Class\nFare Miami R/T","Your DESIRE","Add-On OPTIONS: with SLS","SLS Fare","Bonus City"],["\n\n\n\n\n\n\n\n\n\n\nLos Angeles","\n\n\n\n\n\n\n\n\n\n\n$1,962","\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\nMore for Less","San Juan, PR","$957","-$1,005"],["#rowspan#","#rowspan#","#rowspan#","Rincon, PR","$897","-$1,065"],["#rowspan#","#rowspan#","#rowspan#","Cancun","$1,762","-$200"],["#rowspan#","#rowspan#","#rowspan#","Nassau","$1,803","-$159"],["#rowspan#","#rowspan#","#rowspan#","Mexico City","$1,816","-$146"],["#rowspan#","#rowspan#","#rowspan#","La Romana","$1,725","-$237"],["#rowspan#","#rowspan#","#rowspan#","Montego Bay","$1,607","-$355"],["#rowspan#","#rowspan#","#rowspan#","St. Thomas","$1,029","-$933"],["\n\nSan Francisco","\n\n$1,980","#rowspan#","San Juan, PR","$1,042","-$938"],["#rowspan#","#rowspan#","#rowspan#","La Romana","$1,769","-$211"],["#rowspan#","#rowspan#","#rowspan#","Monterrey, Mexico","$1,760","-$220"],["Philadelphia","$1,030","#rowspan#","San Juan, PR","$994","-$36"],["#rowspan#","#rowspan#","#rowspan#","Antigua, Guatemala","$1,040","$10"]]
[["Home Airport","Originally Planned\nDestination","Normal Business Class\nRound Trip","Add-On Option:\nwith SLS","SLS Biz Class Fare","Bonus SLS City"],["\n\n\n\n\n\n\n\n\n\n\nNew York/JFK","San Francisco","$1,980","San Juan, PR","$1,456","-$524"],["#rowspan#","\n\n\n\nPhoenix","\n\n\n\n$1,560","Mexico City","$1,338","-$222"],["#rowspan#","#rowspan#","#rowspan#","San Juan, PR","$1,366","-$194"],["#rowspan#","#rowspan#","#rowspan#","Cancun","$1,439","-$121"],["#rowspan#","#rowspan#","#rowspan#","Nassau","$1,482","-$78"],["#rowspan#","\n\n\nDallas","\n\n\n$1,190","Montego Bay","$944","-$246"],["#rowspan#","#rowspan#","#rowspan#","Rincon","$997","-$193"],["#rowspan#","#rowspan#","#rowspan#","Nassau","$1,051","-$139"],["\n\n\nSan Francisco","\n\n\n\n\n\nNew York/JFK","\n\n\n$1,870","La Romana","$1,769","-$101"],["#rowspan#","#rowspan#","#rowspan#","Puerto Vallera","$1,776","-$94"],["#rowspan#","#rowspan#","#rowspan#","Nassau","$1,837","-$33"],["\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\nLos Angeles","#rowspan#","\n$2,200","San Juan, PR","$1,689","-$511"],["#rowspan#","#rowspan#","#rowspan#","Cancun","$1,487","-$713"],["#rowspan#","\n\n\n\n\n\nCharlotte","\n\n\n\n\n\n$1,660","Nassau","$898","-$762"],["#rowspan#","#rowspan#","#rowspan#","San Juan, PR","$985","-$675"],["#rowspan#","#rowspan#","#rowspan#","Cancun","$1,285","-$375"],["#rowspan#","#rowspan#","#rowspan#","San Jose Del Cabo","$1,588","-$72"],["#rowspan#","#rowspan#","#rowspan#","Belize","$1,686","$26"],["#rowspan#","\n\n\n\nAtlanta","\n\n\n\n$1,930","Cancun","$1,400","-$530"],["#rowspan#","#rowspan#","#rowspan#","Punta Cana","$1,413","-$517"],["#rowspan#","#rowspan#","#rowspan#","Montego Bay","$1,692","-$238"],["#rowspan#","#rowspan#","#rowspan#","San Juan, PR","$1,841","-$89"]]
[["Route","Normal Business Class Round Trip","Add-On Option: with SLS","Side Trip Cost","Bonus SLC City"],["New York/JFK - SFO","$1,980","San Juan, PR","$1,456","-$524"],["Los Angeles - New York/JFK","$2,200","San Juan, PR","$1,487","-$713"],["New York/JFK - Phoenix","$1,560","Mexico City","$1,338","-$222"],["New York/JFK - Phoenix","$1,560","Cancun","$1,439","-$121"],["San Francisco - New York/JFK","$1,870","La Romana","$1,769","-$101"],["San Francisco - Philadelphia","$1,590","San Juan, PR","$1,585","-$5"]]
[["Home Airport","Originally Planned Destination","Normal Business Class Round Trip","Add-On Option: with SLS","SLS Fare","Bonus SLS City"],["\n\n\n\n\n\nLos Angeles","New York/JFK","$2,200","Cancun","$1,487","-$713"],["#rowspan#","\n\n\n\nAtlanta","\n\n\n\n$1,930","Cancun","$1,400","-$530"],["#rowspan#","#rowspan#","#rowspan#","Nassau","$1,413","-$517"],["#rowspan#","#rowspan#","#rowspan#","San Juan, PR","$1,692","-$238"],["#rowspan#","#rowspan#","#rowspan#","Cancun","$1,841","-$89"]]
[["Home Airport","Originally Planned Destination","Normal Business Class Round Trip","Add-On Option: with SLS","SLS Fare","Bonus SLS City"],["\n\n\n\n\n\n\n\nLos Angeles","New York/JFK","$2,200","Guatemala City","$2,171","-$29"],["#rowspan#","\n\n\n\n\n\n\n\nBoston","\n\n\n\n\n\n$1,613","Cancun","$1,460","-$153"],["#rowspan#","#rowspan#","#rowspan#","Mexico City","$1,501","-$112"],["#rowspan#","#rowspan#","#rowspan#","Punta Cana","$1,520","-$93"],["#rowspan#","#rowspan#","#rowspan#","La Romana","$1,586","-$27"],["#rowspan#","#rowspan#","#rowspan#","Montego Bay","$1,594","-$19"],["San Francisco","#rowspan#","$1,464","San Juan, PR","$1,431","-$33"]]