How to Save 46% on Your Next Transcon Flight (Plus Get a Free Side Trip)

January 2026
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The California Edition: What Bruce Lee would do, Transcon Part 2

Last month we showed New York travelers how Bruce Lee would handle ridiculous transcon fares.

Turns out, he'd do the same thing from California – just with different airports.

The move? Add a "free" destination to lower the fare.

The intelligence? Airline pricing isn't logic. It's patterns you can exploit.

California to New York

We already did the heavy lifting. Ran a zillion fare combinations. Found the openings. We've got your numbers.

This isn't about becoming a fare analyst. This is about using research someone else already completed.

That's Upgrade Intelligence. Not doing more work – doing smarter work.

THE FRICTION
(IT'S THE SAME FROM BOTH COASTS)

Business Class from Los Angeles to New York has been brutal:

  • American Airlines: $2,470+ round-trip
  • Delta: $4,300 to $5,800 round-trip
  • United: $2,300 to $2,610 round-trip

For 11 hours of total flying. Across your own country.

Meanwhile, Delta charges $3,104 to Madrid. United charges less to fly you to Tokyo than at peak times to New Jersey.

The pricing makes no sense – unless you understand it's not about distance or logic. It's about demand, competition, and route economics.

Which means: Where there's friction, there's usually an opening.

THE STRATEGY (QUICK REMINDER)

If you read last month's piece, you know this already. If you're new: Here's the short version.

Airlines price routes based on algorithms that optimize for profit, not logic.

Sometimes by adding a destination – a third flight segment – the total fare is cheaper than flying direct.

Why? Because the airline wants to fill seats on less popular routes. Or because connecting through a hub creates pricing opportunities. Or because their algorithm just does weird things.

Bruce Lee call edit "be like water."

Instead of booking Los Angeles to New York round-trip, you book Los Angeles to New York to Cancun to Los Angeles on Delta and save 45%. Or stop in Phoenix. Or Boston. Or Fort Lauderdale.

Same origin. Same final destination. Same trip. But you add a "free" stop – and save hundreds or thousands of dollars.

Sometimes the savings are modest. Sometimes you knock 50% off. Sometimes you get a free vacation and still pay less.

WHO THIS IS FOR

In The Upgrade Process, Step 2 is about Desires – what you actually want, not what sounds good or what you're "supposed" to want.

This works if you desire:

  • Lower fares without sacrificing comfort or class of service
  • More experience wealth (an extra destination) without spending more money
  • Freedom from the elite status charade that doesn't deliver anymore
  • Flexibility to add leisure to a business trip you can expense
  • A way to outsmart airline pricing instead of just complaining about it

This doesn't work if you need rigid routing, inflexible dates, or if you genuinely prefer simplicity over savings.

That's fine. Upgrade Intelligence isn't about what everyone should do. It's about what works for you, based on what you actually want right now.

THE CHEAT SHEET:
CALIFORNIA-TO-NEW YORK ROUTES THAT WORK

Below are real fares we recently found for March and April 2026. All Business Class. All on major carriers.

Fares change constantly – sometimes hourly – so treat these as proof of concept, not permanent inventory. The strategy works. The specific numbers fluctuate.

To find these fares yourself, use Google Flights' multi-city tool. Plug in your origin (Los Angeles or San Francisco), then New York, then the add-on city, then back home. Toggle dates. The algorithm does the work.

Or hand this special report to your travel advisor, assistant, or kid, and let them run the numbers.

American Airlines

Transcon Business Class pricing as you can see in the Google Flights screenshot below averages $2,490 for nonstop Los Angeles to New York.

FCF’s American Airlines Cheat Sheet:
Save Money + Get a Free Destination

Route Direct Fare Add-On Destination New Fare Savings $ Savings %
Los Angeles - New York/JFK $ 2,490 Chicago $ 2,462 $28 1.12%
Los Angeles - New York/JFK $ 2,490 Las Vegas $ 2,445 $45 1.81%
Los Angeles - New York/JFK $ 2,490 Oklahoma City $ 2,358 $132 5.30%
Los Angeles - New York/JFK $ 2,490 Atlanta $ 2,347 $143 5.74%
Los Angeles - New York/JFK $ 2,490 Charlotte $ 2,252 $238 9.56%
San Francisco - New York/JFK $ 2,537 Fort Lauderdale $ 2,241 $296 11.67%
Los Angeles - New York/JFK $ 2,490 Nashville $ 2,178 $312 12.53%
Los Angeles - New York/JFK $ 2,490 Seattle $ 2,168 $322 12.93%
Los Angeles - New York/JFK $ 2,490 Boston $ 2,142 $348 13.98%
Los Angeles - New York/JFK $ 2,487 Boston $ 2,137 $350 14.07%
San Francisco - New York/JFK $ 2,537 San Juan, Puerto Rico $ 2,065 $472 18.60%
Los Angeles - New York/JFK $ 2,490 Omaha $ 1,859 $631 25.34%
San Francisco - New York/JFK $ 2,537 Boston $ 1,831 $706 27.83%

Delta

Transcon Business Class on Delta as you can see in the screenshot below ranges from $4,800 to $5,800 for nonstop Los Angeles to New York. That's not a fare. That's a ransom.

FCF’s Delta Cheat Sheet:
Save Money + Get a Free Destination

Route Direct Fare Add-On Destination New Fare Savings $ Savings %
Los Angeles - New York/JFK $ 5,100 San Juan, Puerto Rico $ 4,930 $170 3.33%
Los Angeles - New York/JFK $ 5,097 San Juan, Puerto Rico $ 4,880 $217 4.26%
Los Angeles - New York/JFK $ 5,100 Seattle $ 4,815 $285 5.59%
Los Angeles - New York/JFK $ 5,097 Boston $ 4,631 $466 9.14%
Los Angeles - New York/JFK $ 5,100 Portland $ 4,575 $525 10.29%
Los Angeles - New York/JFK $ 5,100 Boston $ 4,451 $649 12.73%
Los Angeles - New York/JFK $ 5,100 San Juan, Puerto Rico $ 4,405 $695 13.63%
Los Angeles - New York/JFK $ 5,097 Aruba $ 4,369 $728 14.28%
Los Angeles - New York/JFK $ 5,100 Aruba $ 4,369 $731 14.33%
Los Angeles - New York/JFK $ 5,097 Miami $ 4,361 $736 14.44%
Los Angeles - New York/JFK $ 5,100 Miami $ 4,321 $779 15.27%
Los Angeles - New York/JFK $ 5,100 Denver $ 4,315 $785 15.39%
San Francisco - New York/JFK $ 5,597 San Juan, Puerto Rico $ 4,755 $842 15.04%
Los Angeles - New York/JFK $ 5,097 Fort Lauderdale $ 4,235 $862 16.91%
Los Angeles - New York/JFK $ 5,100 Phoenix $ 4,220 $880 17.25%
Los Angeles - New York/JFK $ 5,100 Fort Lauderdale $ 4,150 $950 18.63%
Los Angeles - New York/JFK $ 5,100 Miami $ 4,120 $980 19.22%
San Francisco - New York/JFK $ 5,597 San Juan, Puerto Rico $ 4,566 $1,031 18.42%
San Francisco - New York/JFK $ 5,597 Nassau $ 4,555 $1,042 18.62%
San Francisco - New York/JFK $ 5,597 Santo Domingo $ 4,545 $1,052 18.80%
Los Angeles - New York/JFK $ 5,100 Nassau $ 3,901 $1,199 23.51%
Los Angeles - New York/JFK $ 5,100 Boston $ 3,880 $1,220 23.92%
San Francisco - New York/JFK $ 5,597 Nassau $ 4,369 $1,228 21.94%
Los Angeles - New York/JFK $ 5,100 Turks and Caicos $ 3,868 $1,232 24.16%
Los Angeles - New York/JFK $ 5,100 Seattle $ 3,865 $1,235 24.22%
Los Angeles - New York/JFK $ 5,100 Fort Lauderdale $ 3,860 $1,240 24.31%
Los Angeles - New York/JFK $ 5,100 Portland $ 3,825 $1,275 25.00%
Los Angeles - New York/JFK $ 5,100 Bermuda $ 3,759 $1,341 26.29%
Los Angeles - New York/JFK $ 5,100 Bermuda $ 3,759 $1,341 26.29%
San Francisco - New York/JFK $ 5,597 Santo Domingo $ 4,171 $1,426 25.48%
Los Angeles - New York/JFK $ 5,100 Punta Cana, Dom Republic $ 3,646 $1,454 28.51%
Los Angeles - New York/JFK $ 5,100 Montego Bay $ 3,584 $1,516 29.73%
Los Angeles - New York/JFK $ 5,100 San Diego $ 3,576 $1,524 29.88%
Los Angeles - New York/JFK $ 5,097 Santo Domingo $ 3,553 $1,544 30.29%
Los Angeles - New York/JFK $ 5,100 Santo Domingo $ 3,553 $1,547 30.33%
Los Angeles - New York/JFK $ 5,097 Nassau $ 3,466 $1,631 32.00%
San Francisco - New York/JFK $ 5,597 Miami $ 3,942 $1,655 29.57%
San Francisco - New York/JFK $ 5,597 Boston $ 3,845 $1,752 31.30%
Los Angeles - New York/JFK $ 5,397 Nassau $ 3,605 $1,792 33.20%
San Francisco - New York/JFK $ 5,597 Fort Lauderdale $ 3,741 $1,856 33.16%
San Francisco - New York/JFK $ 5,597 Miami $ 3,456 $2,141 38.25%
Los Angeles - New York/JFK $ 5,097 Cancun $ 2,879 $2,218 43.52%
San Francisco - New York/JFK $ 5,597 Boston $ 3,150 $2,447 43.72%
Los Angeles - New York/JFK $ 5,397 Cancun $ 2,944 $2,453 45.45%
San Francisco - New York/JFK $ 5,597 Fort Lauderdale $ 3,040 $2,557 45.69%

United Airlines

United's transcon Business Class as you can see in the screenshot below runs $2,640 to $6,660 round-trip Los Angeles to Newark. Better than Delta, but still a premium for a domestic route.

FCF’s United Cheat Sheet:
Save Money + Get a Free Destination

Route Direct Fare Add-On Destination New Fare  Savings $ Savings %
Los Angeles - New York/Newark $ 2,610 Boston $ 2,503 $107 4.10%
Los Angeles - New York/Newark $ 3,099 Aruba $ 2,718 $381 12.29%
San Francisco - New York/Newark $ 3,491 Fort Lauderdale $ 3,102 $389 11.14%
Los Angeles - New York/Newark $ 3,099 Fort Lauderdale $ 2,697 $402 12.97%
Los Angeles - New York/Newark $ 2,909 San Juan, Puerto Rico $ 2,458 $451 15.50%
San Francisco - New York/Newark $ 3,491 San Juan, Puerto Rico $ 3,008 $483 13.84%
Los Angeles - New York/Newark $ 3,099 Boston $ 2,609 $490 15.81%
San Francisco - New York/Newark $ 3,491 Fort Lauderdale $ 2,940 $551 15.78%
San Francisco - New York/Newark $ 3,491 Aruba $ 2,924 $567 16.24%
San Francisco - New York/Newark $ 3,491 Miami $ 2,881 $610 17.47%
San Francisco - New York/Newark $ 3,491 Boston $ 2,868 $623 17.85%
Los Angeles - New York/Newark $ 3,099 Santo Domingo $ 2,420 $679 21.91%
San Francisco - New York/Newark $ 3,491 Bermuda $ 2,749 $742 21.25%
Los Angeles - New York/Newark $ 3,099 Nassau $ 2,317 $782 25.23%
Los Angeles - New York/Newark $ 3,099 San Juan, Puerto Rico $ 2,197 $902 29.11%
San Francisco - New York/Newark $ 3,491 Santo Domingo $ 2,510 $981 28.10%
San Francisco - New York/Newark $ 3,491 Nassau $ 2,317 $1,174 33.63%
Los Angeles - New York/Newark $ 2,610 Bermuda $ 1,264 $1,346 51.57%
San Francisco - New York/Newark $ 4,098 Boston $ 2,469 $1,629 39.75%
San Francisco - New York/Newark $ 4,298 Nassau $ 2,567 $1,731 40.27%
San Francisco - New York/Newark $ 4,298 Santo Domingo $ 2,510 $1,788 41.60%
San Francisco - New York/Newark $ 5,148 San Juan, Puerto Rico $ 3,261 $1,887 36.66%
San Francisco - New York/Newark $ 5,148 Aruba $ 3,174 $1,974 38.34%

HOW TO FIND THESE FARES YOURSELF

You don't need a PhD in airline pricing. You need 10 minutes and Google Flights.

Here's the process:

  1. Go to google.com/travel/flights
  2. Click "Multi-city" instead of "Round-trip"
  3. Enter: Los Angeles to New York to [Add-on city from table above or experiment with other cities] to Los Angeles
  4. Select Business Class
  5. Toggle dates – pricing fluctuates daily, so experiment
  6. Compare the multi-city total to the direct round-trip fare
  7. If the multi-city fare is lower (and you want the add-on destination), book it

You don't need permission to have more fun, more adventure, more value. You need options. You need leverage.

BE WATER, CALIFORNIA

Bruce Lee didn't fight force with force. He redirected it. Used the opponent's momentum. See openings others missed.

The airlines think this way already. They flow where there's demand. They charge what the market will bear. They discount where there's space.

Now you can, too.

The $4,800 Delta fare from Los Angeles to New York? That's friction.

The $3,040 fare to Ft. Lauderdale (Miami) with New York as a free stopover? That's leverage. That's options. A business expense. That's Upgrade Intelligence working with reality, not against it.

You've already decided to travel. Already budgeted the time and money. Already arranged the time off and the dog sitter.

Don't let that effort dead-end in a single destination when you could redirect it into something twice as valuable for half the cost.

"Be water," Bruce Lee would say.

The airlines already are.

Now it's your turn.

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