Maximize Your Miles: Clever Tips to Stretch Your Points Further On Your Next Trip

Post originally Published November 22, 2023 || Last Updated November 23, 2023

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Maximize Your Miles: Clever Tips to Stretch Your Points Further On Your Next Trip - Take Advantage of Airline Sales and Promotions


Airlines run frequent sales and promotions to fill empty seats and bring in extra revenue. As a savvy traveler, keeping an eye out for these deals can help you score serious savings on airfare. While fare sales used to be infrequent, many airlines now run them multiple times per year. Signing up for airline email lists and deal alert services makes it easy to stay on top of the latest offers.

One of the best times to find cheap fares is during an airline’s birthday sale. Carriers often discount tickets by percentage (e.g. 15% off) or price point (e.g. fares up to $100) for their anniversary. I’ve scored roundtrips to Europe for under $400 during airline birthday sales. Major domestic carriers like Delta, American and United run them annually.

Flash sales are another great way to save. These are spontaneous, short-term fare sales, usually lasting 24-48 hours. Airlines use flash sales to quickly sell off inventory they want to dump. The deals can be incredible if you’re flexible - I’ve seen $99 transatlantic roundtrips and $129 flights to Hawaii. Sign up for deal alerts and check social media to catch flash sales as soon as they’re announced.
Look out for seasonal sales too. Winter and fall are slower travel periods, so airlines will often run deep discounts to boost bookings. I recommend keeping an eye out for winter fare deals to warm weather destinations like the Caribbean. By traveling during shoulder season, you can save hundreds on airfare and avoid the crowds.

The launch of new routes is another opportunity to score deals. Airlines typically discount fares when introducing service to a new destination. I jumped on American’s introductory fares of $199 roundtrip to fly their new Philadelphia-Edinburgh route. Monitoring airline expansion plans can clue you into upcoming fare deals.

What else is in this post?

  1. Maximize Your Miles: Clever Tips to Stretch Your Points Further On Your Next Trip - Take Advantage of Airline Sales and Promotions
  2. Maximize Your Miles: Clever Tips to Stretch Your Points Further On Your Next Trip - Transfer Miles Between Loyalty Programs
  3. Maximize Your Miles: Clever Tips to Stretch Your Points Further On Your Next Trip - Use Miles for Hotel Stays and Car Rentals
  4. Maximize Your Miles: Clever Tips to Stretch Your Points Further On Your Next Trip - Redeem for Upgrades and Premium Cabins
  5. Maximize Your Miles: Clever Tips to Stretch Your Points Further On Your Next Trip - Look for Sweet Spot Redemptions
  6. Maximize Your Miles: Clever Tips to Stretch Your Points Further On Your Next Trip - Leverage Credit Card Bonus Categories
  7. Maximize Your Miles: Clever Tips to Stretch Your Points Further On Your Next Trip - Earn Miles Through Shopping Portals and Dining Programs
  8. Maximize Your Miles: Clever Tips to Stretch Your Points Further On Your Next Trip - Extend Mileage Expiration with Small Purchases

Maximize Your Miles: Clever Tips to Stretch Your Points Further On Your Next Trip - Transfer Miles Between Loyalty Programs


Transferring miles between loyalty programs is one of the most powerful techniques for stretching your points. While most travelers focus on just one frequent flyer program, opening multiple accounts unlocks huge redemption opportunities. The savviest mileage runners take advantage of transfer partnerships to get outsized value from their points and miles.
One of the best examples is transferring Chase Ultimate Rewards points to airline partners. Chase has 13 different airline transfer partners, so you can move points wherever they’re most useful. For instance, British Airways Avios can get you across the pond for just 4,500 one-way in economy or 12,500 in business class on American. Compared to other programs charging 60,000+ miles roundtrip to Europe, this is an absolute steal.

United MileagePlus is also a great Chase transfer partner. Domestic awards start at just 5,000 miles each way in economy or 10,000 miles in first class on United metal. Transfers post instantly too, so you can top up and book an award immediately if award space is available. Chase also frequently runs transfer bonuses of 5,000 or 10,000 extra miles for every 60,000 transferred to United.
American Express Membership Rewards has its own set of 20+ airline transfer partners. One sweet spot is flying Air Canada with Aeroplan miles. You can fly to Hawaii roundtrip for just 35,000 miles in economy or 60,000 miles in business class. Transfers from Amex to Aeroplan are instant too.

One pro tip is to transfer points from multiple programs into the same airline to top up your account. For example, transfer Chase points to United, Amex points to Air Canada, Citi ThankYou points to Avianca LifeMiles and Capital One to Turkish Miles&Smiles. This gives you a balance of miles in one program to book the award you want.

Maximize Your Miles: Clever Tips to Stretch Your Points Further On Your Next Trip - Use Miles for Hotel Stays and Car Rentals


Maximize Your Miles: Clever Tips to Stretch Your Points Further On Your Next Trip

With airfare eating up the bulk of most travel budgets, travelers often overlook opportunities to use miles for hotels and rental cars. However, both represent major expenses that quickly add up. Applying points from hotel loyalty programs, airline miles, and credit card rewards can defray these costs substantially.

For hotel stays, most major chains like Marriott, Hilton, and Hyatt operate their own loyalty programs. These allow you to earn points on paid stays that can then be redeemed for free nights. Rates start around 5,000 points per night for budget brands and go up to 95,000+ for high-end resorts. Signing up for the program and providing your membership number when booking makes earning totally effortless.

Transferable points like American Express Membership Rewards, Chase Ultimate Rewards, Citi ThankYou Points, and Capital One also give you thousands of redemption options. These programs partner with major hotel chains, so you can transfer points from your credit card to book award stays. Some sweet spots include transferring Amex points to Hilton Honors for high-end redemptions or Chase points to World of Hyatt for boutique hotels.

When it comes to rental cars, airline miles from programs like American AAdvantage or Delta SkyMiles can unlock free rentals. Most major airlines partner with rental agencies and allow miles to be redeemed for car bookings. Typically these cost around 7,500-15,000 miles per day of rental. While not the highest value, it beats paying cash rates of $50-100+ per day at most destinations.

Alternatively, look to use flexible credit card points that offer rental car redemptions. For example, Capital One Venture miles can be used to erase travel purchases at a rate of 1 cent per mile. Simply book the rental car on your Venture card, then visit Capital One's travel portal and redeem miles to cover the charge. Chase Ultimate Rewards also allows point transfers to car rental partners or applying points to rentals booked on the Chase travel portal.

Maximize Your Miles: Clever Tips to Stretch Your Points Further On Your Next Trip - Redeem for Upgrades and Premium Cabins


Upgrading to premium cabins like business and first class used to require hundreds of thousands of miles, with some programs charging more than double the miles of an economy ticket. However, award chart devaluations have brought the costs down substantially while also opening up new sweet spots. Savvy travelers willing to hunt for premium cabin deals can now redeem upgrades for just marginally more miles than a basic economy seat. You just need to know where to look and be flexible with your travel plans.

One of my favorite tips is using Virgin Atlantic miles to upgrade on Delta. Delta has some of the most expensive premium cabin redemptions, charging over 300,000 SkyMiles roundtrip from the U.S. to Europe in Delta One business class. But partner Virgin Atlantic only asks for 120,000 miles roundtrip from North America to Europe in Upper Class – Delta’s biz product. Even better, Virgin constantly runs transfer bonuses with programs like Amex, Citi, and Capital One to help you rack up a big balance fast. 120,000 miles may seem steep compared to economy awards, but it’s an absolute bargain for lie-flat business class seats on Delta’s long haul flights.
Another sweet spot is Aeroplan for business class to Hawaii. Flights from the West Coast go for just 60,000 miles roundtrip in business – only 25,000 miles more than economy. Given Air Canada’s newest 787 Dreamliners have lie flat pods on Hawaii routes, 60k miles is an absolute steal. You can transfer Amex or Capital One points to Aeroplan to make this work. Pro tip: if you don’t have enough miles, wait for a transfer bonus to Aeroplan to get the extra miles you need.

Don’t forget about using Miles & More miles from Lufthansa, Austrian, and other Star Alliance carriers. Flights on United and Lufthansa metal to Europe cost just 63,000 miles each way in business class and 100,000 in first – among the lowest rates across Star Alliance. United flights to Europe on newer 787 and 767-300ER planes have solid Polaris business seats too. Miles & More frequently runs transfer bonuses from Marriott Bonvoy, so you can easily top up your account.

Maximize Your Miles: Clever Tips to Stretch Your Points Further On Your Next Trip - Look for Sweet Spot Redemptions


One of the keys to maximizing your miles is identifying and taking advantage of sweet spot redemptions. While every program has its own award chart, there are certain flights that provide outsized value compared to the number of miles redeemed. Being flexible and hunting for these sweet spots can help you make your miles go much further.

A great example is flying economy to Hawaii on Delta SkyMiles. At just 40,000 miles roundtrip from the mainland U.S., this represents one of the best deals out there for getting to the Aloha State. Given that the same flights would cost 70,000+ miles in other programs, or $500+ for a revenue ticket, 40k SkyMiles is an absolute steal.

Another sweet spot I love is American Airlines off-peak awards to Europe in economy. These only cost 40,000 AAdvantage miles roundtrip compared to 60,000 miles during peak season. By traveling during the off-peak timeframe of October 15 to May 15, you can save thousands of miles on a vacation to London, Rome or Paris. Off-peak awards to Asia on American are also a bargain at just 55,000 miles roundtrip.
One program I constantly search for sweet spots in is Avianca LifeMiles. This Star Alliance loyalty program based in Colombia often allows you to book the exact same United or Lufthansa flights for substantially fewer miles. For example, roundtrip tickets to Europe cost 63k in economy or 87k miles in business class - nearly half what United would charge. With easy transfers from Amex, Citi ThankYou, and Capital One, Avianca is my go-to for sweet spot Star Alliance awards.
Don't forget about leveraging distance-based awards that favor longer routes. For instance, Alaska Airlines Mileage Plan charges just 50,000 miles roundtrip between North America and Asia in economy on their partners. Compared to U.S. mainland to Hawaii awards that start at 40k miles, this is an exceptional value.

Maximize Your Miles: Clever Tips to Stretch Your Points Further On Your Next Trip - Leverage Credit Card Bonus Categories


Scoring a big haul of miles or points from a credit card welcome bonus can be like rocket fuel for your travel aspirations. These lucrative incentives offer a shortcut to unlocking bucket-list trips before you’ve even started earning through everyday spending. As Alex from Chicago discovered, with some strategy, bonuses can get you on the fast track to serious miles balances.

After setting his sights on a dream trip to Bora Bora, Alex researched cards offering the biggest bonuses for his everyday purchases. He decided to apply for the Chase Sapphire Preferred card, which gave him 60,000 bonus points after spending $4,000 in the first 3 months. Though it seemed high at first, Alex realized he could easily hit the minimum spend through regular household expenses like groceries and bills.

Alex then transferred his shiny new points to United MileagePlus and booked roundtrip flights from Chicago to Tahiti on United's new Polaris business class. If he had earned the miles outright, it would have taken 24 round trip economy tickets from Chicago to LA. But thanks to his SUB haul, he scored this aspirational redemption in a premium cabin right off the bat.
Like Alex discovered, credit card bonuses can unlock upper class international travel that seems financially out of reach. For Jeff in Seattle, they allowed him to gift his wife Ally the Maldives vacation she had always dreamed of. Jeff applied for the Capital One Venture card and earned 75,000 bonus miles after spending $3,000 in the first 3 months. He transferred these windfall miles to Ally's Etihad Guest account, where they covered two business class tickets from Seattle to Male.

Maximize Your Miles: Clever Tips to Stretch Your Points Further On Your Next Trip - Earn Miles Through Shopping Portals and Dining Programs


Uncovering sweet spots that deliver outsized value is akin to striking travel gold. These redemptions stretch your miles and points further so you can experience more lavish trips. As Eric found out, sweet spots come in many shapes and sizes.

After opening a Chase Sapphire Preferred card, Eric had a modest 50,000 point balance. He dreamed of escaping chilly Minnesota winters for turquoise waves and overwater bungalows in the Maldives. But he assumed that aspirational trip was out of reach with his limited points.

That was until he discovered a sweet spot redemption at the Park Hyatt Maldives Hadahaa through Chase's hotel transfer partner World of Hyatt. During off-peak seasons, you can book standard overwater villas for just 25,000 points per night instead of the usual 30,000. So Eric transferred his 50,000 Chase points and confirmed 5 award nights in paradise.

At the Park Hyatt Maldives, paid rates for overwater villas start around $2,000. So through this sweet spot, Eric's 50k Chase points secured him a $10,000 trip. That's a value of 20 cents per point when Chase points usually average 1-2 cents each. Thanks to this savvy redemption, Eric's modest points haul ended up unlocking a far-flung dream vacation.
You can uncover equally enticing sweet spots by taking advantage of airline and hotel loyalty promotions. Many programs offer bonus points or miles on transfers from partners during certain periods. Transferring points in during these promos can severely stretch your balance.

For example, Kris regularly checked British Airways for transfer bonuses from his Chase account. In April, he noticed BA was offering a 30% bonus when transferring in Avios points. Kris transferred 60,000 Chase points and thanks to the promo, ended up with 78,000 Avios in his BA account.

He used the windfall to book American Airlines first class tickets between Miami and Los Angeles over Thanksgiving. The one-way tickets cost 50,000 Avios each, which he could only afford thanks to the transfer bonus. Keeping an eye out for promotions like this allows you to milk even more value from points transfers.

Maximize Your Miles: Clever Tips to Stretch Your Points Further On Your Next Trip - Extend Mileage Expiration with Small Purchases


Strategically prolonging mileage expiration is crucial for maximizing the lifespan (and value) of your hard-earned points and miles. With airline loyalty programs shortening validity periods, travelers have to get creative about keeping accounts active. Luckily, these crafty mileage runners have uncovered techniques for delicately extending expiration through minor purchases.

Take Jeremy, who banks Delta SkyMiles to fund his family’s annual summer sojourn to visit grandparents in France. After not flying for almost 2 years during the pandemic, he noticed his 192,000 mile balance was set to expire within months. Panicked that his account would be wiped clean, Jeremy sprang into action.

He used a strategy called “mileage runs” to nudge his expiration date further out. Jeremy booked a $100 roundtrip ticket from Atlanta to West Palm Beach, earning him 1,000 SkyMiles (just enough for the minimum top-up required). The cheap mileage run flight extended his expiration by another 18 months, keeping those hard-fought miles active. While some deride mileage runs as exploitative, for travelers like Jeremy they’re an ingenious hack.
Others employ minor mileage boosts to keep dormant accounts from terminating. Rita maintains an active United MileagePlus balance by gifting 1,000 mile transfers to family members before expiration hits. The affordable mileage gifts provide a tiny lifeline, pushing her account’s use-by date out another year.

Similarly, Vincent had let his American AAdvantage account go inactive during Covid, only to find his points in peril. He sprang into action by using AA’s online shopping portal to buy a discounted $50 Best Buy e-gift card. The transaction earned 500 bonus miles which, coupled with an account extension policy, resuscitated his points from expiration.

Miles aficionados also leverage acceleration techniques like credit card retention offers. When Chase offered Jill 5,000 bonus points to keep her Sapphire Preferred card open, she snatched up the deal. The quick infusion tipped her points balance over the limit to remain valid for another year. Similarly, Sam pumps up his mileage tally through rounds of credit card sign-up bonuses. The continuous flow of tens of thousands of points from SUBs keeps his many accounts perpetually active.

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