Success stories

Real trips, booked with points people already had.

Every trip below is one we actually booked. Some were planned for clients, some are our own. In each one you'll see what it cost in points, what the same booking would have cost in cash, and the specific decision that made the difference.

My own trip

Minneapolis to Portugal, business class out

Family of four · Business class over, economy home

Two things made this one work. Avianca LifeMiles was running a transfer bonus from Amex Membership Rewards, which brought the outbound down sharply. Then I built it as a mixed-cabin award, taking economy on the short Minneapolis to Toronto leg so the points went toward the business-class part that actually mattered. I also targeted TAP on purpose: their business cabin is a 2-2 layout, which meant we could corral the kids into pairs instead of scattering four people across the plane.

What it cost

45,000 Amex Membership Rewards + $60 each to Faro, transferred to Avianca LifeMiles during a transfer bonus. 15,000 Virgin Atlantic points + $80 each for Lisbon back to Minneapolis.

Cash price avoided

$4,200

Round-trip in business, or about $1,000 in economy. We flew business over and economy home.

Client trip

Phoenix to Madrid in business class

One traveler joining a group trip · Business class

Award rates move, so rather than booking the first seat available we tracked this route over time and waited for American to release space at a genuinely good rate. The return went through Chicago on Iberia Avios, with an inexpensive cash fare covering the last leg home. Marriott free nights handled the hotel in Madrid.

What it cost

62,000 American Airlines miles + $81 outbound. 40,000 Iberia Avios + $120 back to Chicago, plus a cheap cash flight home.

Cash price avoided

$4,500

Client trip

Minneapolis to Portland for a girls' trip

A group of friends · Delta nonstop

Virgin Atlantic was already the best-priced way to book this Delta flight, which surprises people who assume you need SkyMiles to fly Delta. The timing then lined up with a 30% transfer bonus from Amex, and stacking the two turned a good redemption into a great one.

What it cost

33,000 Virgin Atlantic points round-trip, which cost only 26,000 Amex Membership Rewards after a 30% transfer bonus.

Cash price avoided

$527

My own trip

Minneapolis to Palm Springs, five nights in a suite

Family of four · Delta nonstop · One-bedroom suite

Marriott free night certificates can only be redeemed on a property's base-level room, which normally rules out anything resembling a suite. The way around it was finding a Marriott Vacation Club property attached to the JW Marriott, where the base room is a full one-bedroom suite and guests still get access to the JW's amenities. Five certificates from a single signup bonus covered the whole stay, and the flights came out of a Delta award sale.

What it cost

21,000 SkyMiles + $11.20 each round-trip, booked during a Delta award sale. Five Marriott free night certificates from a signup bonus for the hotel.

Cash price avoided

$1,750

For the hotel, plus about $300 each for the flights.

Client trip

Minneapolis to Chicago for a long weekend

Two friends · Four nights at the Chicago Athletic Association

Hyatt's devaluation made a lot of its city hotels harder to justify on points, and plenty of people wrote the program off afterward. This booking still held up: four nights at the Chicago Athletic Association for 80,000 points, against a cash rate over $2,000.

What it cost

20,000 Avianca LifeMiles + $11.20 per person, round-trip. 80,000 Hyatt points for four nights.

Cash price avoided

$2,148

For the hotel, plus $457 per person for the flights.

My own trip

Minneapolis to Barcelona, home from Amsterdam

Two travelers · Business over, premium economy home

Flying into one city and home from another meant no backtracking at the end of the trip. The cabin split was deliberate: business class on the overnight flight east, where a lie-flat seat genuinely changes how the first day goes, and premium economy on the daytime flight home, which is still a comfortable experience for far fewer points. The work was in finding both legs at Flying Blue's lowest award level.

What it cost

95,000 Flying Blue miles each, round-trip.

Cash price avoided

~$3,000

Each.

Client trip

Minneapolis to Athens

A couple · Round-trip economy

Not every good redemption is a lie-flat seat. 74,000 Flying Blue miles between the two of them covered a round-trip to Greece, turning what is usually one of the biggest line items in a trip budget into a rounding error.

What it cost

37,000 Flying Blue miles per person, plus about $300 in taxes and fees.

Cash price avoided

$1,200

Per person.

These are real bookings, with the points and cash figures as they stood on the day each one was booked. Award space, mileage rates, and transfer bonuses all change, so treat these as examples of what points can do rather than prices we can promise. What your own points can unlock depends on your balances, your dates, and what's available when you book, which we'll pin down together before you book anything.

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