Hey Jetsetter,
Today, I’m sharing a detailed booking breakdown to show how I use points and miles to unlock incredible value—even for domestic flights. Whether planning your next ski trip or a sunny getaway, this strategy can save you big with your miles game for the year ahead.
The Backstory: Birthday Ski Trip Pivot
Living in the SF Bay Area, we get to snowboard at Lake Tahoe often. For my birthday, I wanted to mix it up with a weekend at Whistler. But plans changed when I got a last-minute invite to a private ski resort near Big Sky, Montana. It's by far my favorite ski mountain in the world!
Booking Breakdown: SFO → BZN ($484 Flight for 10K Points)
Usually, we stick to OneWorld Alliance partners like American Airlines and Alaska Airlines. However, Alaska had limited flights, so we opted for United this time.
With my wife and I holding United Silver status (earned via work travel and Marriott Bonvoy Titanium Elite status), we scored free checked bags and complimentary Economy Plus seats—perfect for ski gear!
Here’s the process:
1️⃣ Flight Search: Found the $484 flight on Google Flights.
2️⃣ United Mileage Pricing: 15K miles one-way.
3️⃣ Air Canada Aeroplan: Same flight for just 10K points thanks to their distance-based award chart.
4️⃣ Amex Transfer: Redeemed 10K American Express Membership Rewards points to Air Canada.
5️⃣ Booking: Paid just $33 in fees for the flight.
6️⃣ Silver Status Benefits: Linked our award booking to our United MileagePlus accounts to select Economy Plus seats for free.
Why This Booking Worked
Here’s the secret: Air Canada’s Aeroplan uses fixed partner award charts, meaning lower point costs for specific routes. Pairing this with the 20% Chase to Aeroplan transfer bonus could’ve reduced the price to just 8K points. However, I used Amex points since we have a more extensive stash there.
Note: the 20% transfer bonus ends soon, on 1/15/2025
The result? 5.6 Cents Per Point (CPP)—560% better than booking through a travel portal.
Return Flight Options
United charged 23K miles for the return leg, and Aeroplan didn’t show availability. Here were my choices:
1️⃣ Pay $484 cash.
2️⃣ Redeem 23K United miles.
3️⃣ Use 12K AA miles for Alaska Airlines with a layover.
4️⃣ Book an Alaska flight and credit it to American Airlines’ elite status.
I know these points booking strategies can feel overwhelming, but this is exactly what I help our members with inside the private Miles Ahead Pro community. Interested in personalized points & miles guidance from me? Click here to learn more
Since we’re aiming to requalify for AA Executive Platinum elite status (my wife is very close), and I'm aiming to hit 250,000 Loyalty Points (& AAdvantage miles), we chose option 4 to maximize Loyalty Points towards our elite statuses.
Elite AAdvantage Workshop: Coming Soon
Last year, I hosted live workshops on earning American Airlines elite status, helping attendees save thousands and hit their desired elite status tier—some without flying!
If you’re interested in the 2025 Elite AAdvantage Workshop, click below to join the waitlist:
👉 Join the Workshop Waitlist
Your Feedback Matters
This email dives deep into my booking process and strategy. Did you find it helpful? Reply or vote below—I’d love to know!
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That’s all for today! I’m wrapping up an epic bluebird powder day in Montana.
Chris Ollie
Founder, Points Passport
PS: Want personalized help with your points & miles for 2025? Check out the Miles Ahead Pro Skool community!
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Chris Ollie
Points Passport
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