Key Points

• Southwest and JetBlue don't have blackout dates, making them reliable backup options when traditional award availability vanishes during peak holiday periods.
• Positioning flights to alternate airports can unlock award space that doesn't exist from major hubs, often saving you 30,000+ points compared to cash fares.
• Hotel points become more valuable than airline miles during holidays since accommodations rarely have blackout dates and can be combined with positioning strategies.

Introduction

Holiday travel with points feels impossible when you search for award flights and see nothing but "no seats available" messages staring back at you. Thanksgiving week, Christmas, and New Year's consistently rank as the worst times to find award availability, with some routes showing zero business class seats for months.

But here's what most points enthusiasts miss: holiday travel isn't about finding the perfect award flight from your home airport. It's about using points strategically across multiple programs, being flexible with your approach, and knowing which backup plans actually work when award seats disappear.

I'll show you exactly how to book holiday travel using points when traditional award availability dries up completely.

Why Holiday Award Availability Disappears

Airlines know exactly what they're doing during peak travel periods. Revenue management systems identify high-demand dates and pull award seats from inventory months in advance, directing those seats to cash-paying customers who'll pay premium prices.

The result? Award availability for major holidays typically gets released in three waves: 330-365 days out when the schedule opens, 14-21 days before departure when airlines assess remaining inventory, and occasionally 24-72 hours before the flight for last-minute releases.

That middle period from 60-15 days before departure is where award seats become nearly impossible to find for holiday travel.

Programs Without Blackout Dates

Southwest Rapid Rewards

Southwest operates on a revenue-based model where every seat can be booked with points. During holidays, you'll pay more points than usual, but seats remain available when other programs show nothing.

The math works because Southwest prices awards based on the cash fare. A $400 Thanksgiving flight might cost 26,000-30,000 points instead of the typical 12,000-15,000, but that's still better than paying cash or transferring 50,000+ points to another program only to find zero availability.

The Southwest Companion Pass becomes incredibly valuable during holidays. One person flies on points while your companion flies free (excluding taxes), effectively cutting your points cost in half on expensive holiday fares.

You can earn the Companion Pass by flying 100 qualifying one-way flights or earning 135,000 qualifying points in a calendar year. The fastest route for most people involves opening two Southwest credit cards and meeting minimum spend requirements strategically.

JetBlue TrueBlue

JetBlue also offers revenue-based pricing with no blackout dates. Their points maintain relatively consistent value even during peak periods, typically hovering around 1.3-1.5 cents per point.

For popular holiday routes to Florida, the Caribbean, or Northeast destinations, JetBlue often releases more award inventory than legacy carriers because their entire business model depends on filling seats rather than upselling premium cabins.

Chase Ultimate Rewards Portal

When you have the Chase Sapphire Reserve, you can book any cash fare through the Chase portal at 1.5 cents per point. The Chase Sapphire Preferred offers 1.25 cents per point.

This guaranteed floor value means you'll never be stuck without options during holidays. A $600 roundtrip becomes 40,000 points with the Sapphire Reserve or 48,000 with the Preferred, regardless of award availability through transfer partners.

The portal shines during holidays because it bypasses award inventory entirely. You're essentially converting points to cash and booking regular tickets.

Positioning Flight Strategies

What Positioning Flights Are

A positioning flight means flying to a different city first, then catching your main flight from there. This sounds counterintuitive until you see the numbers.

Example: Chicago to New York direct shows no award availability for Thanksgiving week. But Chicago to Toronto has plenty of award space, and Toronto to New York also has availability. Your "positioning flight" gets you to Toronto, where better award options exist.

Finding Profitable Positioning Routes

Use Seats.Aero to search multiple departure cities simultaneously. Premium accounts let you set up alerts for specific routes and dates, sending notifications when award space opens up.

West Coast travelers often position through Seattle or Vancouver to access Alaska Airlines and Air Canada award space that doesn't exist from California. East Coast travelers position through smaller airports like Providence, Hartford, or even Montreal.

The math works when positioning flights cost 7,500-12,500 points but unlock business class awards that would otherwise be impossible to book. You're spending an extra 10,000-15,000 points total but accessing seats worth $3,000-5,000 in cash value.

Positioning Flight Booking Strategy

Book positioning flights on Southwest or with Ultimate Rewards portal bookings. Both offer free cancellations, giving you flexibility if award space opens up later on your preferred route.

Leave at least 3-4 hours between your positioning flight arrival and main flight departure. Longer connections are better during holidays when delays become more common. You're not checking bags for positioning flights because that adds complexity and risk.

Consider booking positioning flights the night before your main departure, especially for morning holiday flights. The extra hotel night costs points but eliminates the stress of tight connections during peak travel chaos.

Alternative Airport Tactics

Secondary Airport Advantage

Major hub airports like Atlanta, Chicago O'Hare, and Dallas have the worst award availability during holidays because airlines prioritize revenue passengers on these routes. Secondary airports often maintain better award space because they're not primary revenue generators.

New York area travelers should search Newark, JFK, LaGuardia, and even Westchester or Islip. Los Angeles travelers check Burbank, Long Beach, and Orange County alongside LAX. The extra driving time pays off when you find business class awards that don't exist at main airports.

Alaska Airlines frequently releases more award space from Seattle, Portland, and smaller West Coast cities than from major California hubs. Their Mileage Plan partnership with Virgin Atlantic offers interesting routing options through London that bypass crowded domestic hubs entirely.

International Gateway Strategy

Flying to Canada or Mexico first can unlock completely different award availability. Air Canada, Aeromexico, and smaller carriers maintain separate award inventory from U.S. airlines.

Transfer Chase or Amex points to Aeroplan (Air Canada's program) and search Toronto, Montreal, or Vancouver as departure cities. The award charts often show space on the same Star Alliance flights that appear sold out when searching from U.S. cities.

This works because foreign carriers allocate award seats differently than U.S. airlines. They view North American connecting passengers as feed traffic for their international flights, releasing more space to fill those long-haul premium cabins.

Hotel Points Strategy for Holidays

Why Hotels Beat Flights During Holidays

Hotel loyalty programs rarely impose blackout dates because hotels benefit from occupancy regardless of payment method. Marriott Bonvoy, World of Hyatt, and Hilton Honors let you book any standard room with points when availability exists for cash bookings.

This creates opportunities when flight awards disappear but hotel awards remain bookable. You can position to an alternative city the night before, stay on hotel points, then catch better award flights the next morning.

The math often favors using points for hotels during holidays while paying cash or using portal bookings for flights. A peak-season Hyatt might cost 30,000 points but would cost $500-700 in cash. That same 30,000 Chase points only covers $375-450 worth of flights through the portal.

Fifth Night Free Advantage

Marriott Bonvoy and World of Hyatt offer fifth night free on award bookings. This becomes incredibly valuable for longer holiday stays because you're getting 20% off your points cost automatically.

A five-night Thanksgiving stay that would normally cost 125,000 points only costs 100,000 with the fifth night free. That 25,000-point savings could cover your positioning flights or holiday flights on Southwest.

American Express Membership Rewards transfer to Marriott at 1:1 ratios, making it easy to move points for hotel stays when flight awards aren't available. Amex also transfers to Hilton at 1:2, giving you incredible value for holiday hotel stays at lower-tier properties.

Hotel + Flight Packages

Book hotels in cities with better award flight availability, essentially creating your own positioning strategy with accommodation included. Stay in Boston the night before Thanksgiving and fly out of Logan instead of dealing with New York's airport chaos and non-existent award space.

Use Hilton Honors points for airport hotels near secondary airports. Hilton often has excellent availability at airport properties, and their points go further than other programs. A 40,000-point Hilton stay near a secondary airport could unlock award flights that would cost 70,000-100,000 points from major hubs.

Last-Minute Award Availability

The 14-Day Window

Airlines release award seats approximately 14 days before departure when they can better predict load factors. Set up alerts through ExpertFlyer or Seats.Aero for your desired routes starting 21 days before travel.

Business class awards appear more frequently than economy during this window because airlines would rather fill premium cabins with award travelers than fly with empty seats. This seems counterintuitive, but empty business class seats generate zero revenue while award bookings at least move points out of the system.

Have your points already transferred and ready to book when space appears. Award seats during this window disappear within hours, sometimes minutes. You can't wait for points to transfer from Chase or Amex because that takes 1-3 days in most cases.

Waitlist Strategies

Several programs offer award waitlists that can clear even on popular holiday routes. United MileagePlus and Air Canada Aeroplan both maintain waitlists that clear with surprising frequency 7-14 days before departure.

Book the waitlist as early as possible, even if it's 100+ days before travel. Your position in the waitlist queue matters, and earlier bookings get priority when seats open up. Meanwhile, book a backup option using Southwest or the Chase portal that you can cancel if the waitlist clears.

The waitlist strategy works best for premium cabins because those are the seats most likely to open up last-minute. Economy award space that's gone during holidays typically stays gone.

Credit Card Welcome Bonuses

Building Points for Next Year

Start earning points now for next year's holiday travel. The best credit card welcome bonuses put you in position to book holiday travel 12-18 months in advance when award availability is actually decent.

The Chase Sapphire Preferred offers 60,000 Ultimate Rewards points after spending $4,000 in three months. Those points can book $750 worth of flights through the portal or transfer to partners when better availability appears.

American Express Gold Card currently offers 90,000 Membership Rewards points after spending $6,000 in six months. That's enough for multiple domestic award flights or significant progress toward international business class awards.

Business credit cards offer higher welcome bonuses without counting against Chase's 5/24 rule. The Southwest Performance Business offers 80,000 points after spending $5,000, putting you more than halfway to Companion Pass status.

Strategic Application Timing

Apply for cards 9-12 months before holiday travel, giving you time to meet minimum spend requirements and accumulate additional points through everyday spending. This timeline also lets you maximize category bonuses throughout the year.

Focus on flexible points currencies like Chase Ultimate Rewards, Amex Membership Rewards, and Capital One miles. These transfer to multiple airline and hotel partners, giving you maximum flexibility when holiday award availability opens up.

Alternative Holiday Destinations

Off-Peak Holiday Travel

Consider celebrating holidays at different times. Flying the weekend before Thanksgiving or the week after Christmas dramatically improves award availability while maintaining the holiday experience.

This approach works especially well for families without school-age children or remote workers with flexible schedules. You're getting the same destinations and experiences for 50-70% fewer points.

Award space to Europe actually improves during American holidays because fewer Europeans travel during Thanksgiving and Christmas week. You can find excellent business class availability to London, Paris, or Frankfurt during peak U.S. holiday periods.

Domestic Alternatives

Skip the traditional holiday destinations entirely and explore places that don't see holiday crowds. National parks, mountain destinations, and Southwest cities often have excellent award availability during holidays because they're not traditional family gathering spots.

Marriott Bonvoy and World of Hyatt both have excellent properties in Sedona, Park City, and other outdoor destinations where holiday availability remains strong. You're creating new holiday traditions while using points efficiently.

Conclusion

Holiday travel with points requires abandoning the traditional approach of searching for direct flights from your home airport to your destination. The strategies that work involve Southwest's no-blackout-date policy, positioning flights to unlock hidden award space, prioritizing hotel points over flights, and timing your bookings for the 14-day last-minute release window.

Start building points now through credit card welcome bonuses so you're ready to book 330+ days in advance when next year's holiday award space opens. Set up award alerts for multiple routing options including positioning cities and secondary airports. Most importantly, stay flexible with dates, destinations, and routing because rigid holiday travel plans and award bookings don't mix well.

The combination of these strategies turns impossible holiday award bookings into manageable projects. You won't always get the exact flights you want on the exact dates you prefer, but you will get home for the holidays while keeping your points balances intact.

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