Get two (bigger) trips — for the price of one (small) round-trip... with American, Delta, and United
In March we did a deep dive into FCF’s Stopover Loophole Strategy, which we’re now calling the Stopover Double Upgrade Strategy (SDUS) because of its dual-improvement nature.
It's a travel strategy that turns ordinary trips into extraordinary, bigger experiences without breaking the bank – and actually saves money at the same time. We showed you how a Los Angeles-Miami round-trip for $1,942 in Business Class on American Airlines could drop to $960 when you add San Juan, Puerto Rico, as a stopover. That's $982, or 51% less, plus the bonus Caribbean win.
The concept is elegant: you're not breaking the system. You're dancing between its cracks. Think of Puerto Rico or Cancun not as a beach, but as a scalpel — slicing almost $1,000 off your fare.
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)
What About Delta and United?
We last focused primarily on American Airlines. This month we we’re expanding our deep dive to include Delta and United to uncover free and cheaper-than-free side trips. We've systematically tested 68 routes across all three major carriers, and the results validate what we hoped: the Stopover Double Upgrade Strategy isn't carrier-specific — you're dancing between cracks that exist industry-wide.
What started as an American Airlines specialty has become a multi-carrier goldmine. The Caribbean remains king, but now we have routing flexibility across Delta, United, and American networks. The side trip cities that worked before still work, but now we have fresh options, better carrier matching, and — in some cases — even deeper discounts.
SDUS Sample Savings
Here's proof that the Stopover Double Upgrade Strategy works also for Delta and United:
Delta's Greatest Hits
Los Angeles → Atlanta + Cancun
The SDUS Difference: COST SAVINGS: $1,135 / 50% LESS DOUBLE BENEFIT: Save $1,135 + flight to Mexico
Additional Delta Power Plays:
- Los Angeles → New York City + Cancun: normally $2,399 → add Cancun drops to $1,256 (48% savings)
- Los Angeles → Atlanta + Montego Bay: normally $2,289 → add Montego Bay drops to $1,520 (34% savings)
Typical Los Angeles – Atlanta Fare on Delta.com
Los Angeles –Atlanta – Cancun SDUS Strategy Pricing on Delta.com
United's Sweet Spots
San Francisco → Houston + San José del Cabo (Business Class)
The SDUS Difference: COST SAVINGS: $357 / 29% LESS DOUBLE BENEFIT: Save $357 + flight to Mexico
Additional United Opportunities:
- San Francisco → Miami + Nassau: normally $1,958 → add Nassau and drops to $1,444 (26% savings)
- Newark → Los Angeles + Cancun: normally $2,232 → add Cancun and drops to $1,796 (20% savings)
San Francisco - Houston Business Class (left) on United.com San Francisco - Houston - San Jose del Cabo Business Class (right)
American's Continued Excellence
Los Angeles → Miami + Cancun
The SDUS Difference: COST SAVINGS: $1,053 / 53% LESS DOUBLE BENEFIT: Save $1,053 + flight to Caribbean
Where Does SDUS Work Best Now?
The strategy doesn't work everywhere all the time, but spans all three major carriers with distinct patterns:
American Airlines Best Bets
Works best with these low-cost add-on destinations: Cancun, San Juan, Nassau, Puerto Vallarta, Montego Bay, La Romana (Dominican Republic), Virgin Islands
When ordinarily flying TO American's hubs: Miami, Charlotte, Dallas, Phoenix and on longer flights from Los Angeles, and San Francisco to New York and Miami, and from New York to San Francisco or Los Angeles, for example.
Delta Best Bets
Works best with Mexican add-on destinations: Cancun, Puerto Vallarta
When ordinarily flying TO Delta's hubs: Los Angeles (LAX) and Atlanta (ATL) on longer flights from Los Angeles to New York and Atlanta, and From New York to Los Angeles, for example.
United Best Bets
Works best with select Caribbean and Mexican add-on destinations: Nassau, San José del Cabo, Puerto Vallarta, Barbados
When ordinarily flying TO United's hubs: Los Angeles (LAX) and San Francisco (SFO) to destinations like Boston and New York on longer flights from West Coast to East Coast via select Caribbean islands, and from San Francisco to Texas via Mexico, for example.
Note: Some cities perform differently depending on the carrier — Cancun crushes it on Delta and American but barely registers on United, while Nassau works beautifully on United but can backfire elsewhere. The key is testing your specific route combination.
The Booking Playbook
Side Trip Testing: The Hierarchy Method
Don't randomly guess at side trip cities, first. Use this testing hierarchy based on our current success rates, then move on to exploring your desired other destinations:
Tier 1 Cities (Test First):
- Cancun — Works across all carriers, consistently 20%-50% savings
- San Juan — American Airlines gold, mixed results elsewhere
- Nassau — United’s favorite, Delta wildcard
Tier 2 Cities (Test Second):
- Puerto Vallarta — Strong on Delta transcontinentals
- Montego Bay — Reliable 15%-30% performer across carriers
- San José del Cabo — United’s Mexican sweet spot
Timing Insights: When the Loophole Opens Widest
Stopover Duration: Both overnight and multi-day stopovers can deliver massive savings. Single overnight stopovers often unlock some of the biggest discounts because the algorithm treats it as efficient routing rather than vacation planning. Multi-day stopovers (two to four days) work great for leisure combinations. Week-long stops can push you into "multi-city vacation" pricing territory where savings disappear.
Travel Window Sweet Spot: three to six months out seems optimal. Too far out and the algorithms haven't fully loaded; too close and inventory constraints kick in.
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.
Different airlines now offer different SDUS deals and schedules — so locking yourself into loyalty to one airline locks yourself out of options. That's as true with SDUS as any other strategy. That's why I've been advocating for loyalty-free agency for decades.
SDUS Deal Directory 68 Routings to Use Now
Pre-Baked Sample Delta Steals
Pre-Baked Sample United Steals
Pre-Baked Sample American Steals
Closing Arguments: The System Has More Cracks Than We Thought
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?
This month proved that SDUS isn't a glitch — it's a feature. These aren't random accidents in airline pricing; they're systematic blind spots that exist across multiple carriers, multiple routes, and multiple booking windows.
Think of airline pricing algorithms like massive, intricate clockwork. Most travelers see the face of the clock and accept whatever time it shows. But we've learned to read the gears underneath. We're not breaking the mechanism; we're understanding its rhythm well enough to know when it's about to chime.
The airlines built these pricing systems to maximize revenue from conventional travelers. But conventional travelers don't read First Class Flyer. They don't test stopover combinations systematically. They don't treat Caribbean islands like chess pieces in a fare arbitrage game.
You do. And that makes all the difference.
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.
Until then, see you up front.