Too Late for Holidays? 3 Points Hacks to Save Now

Introduction: It’s Not Too Late (If You Stop Thinking Like a Tourist)

Most travelers think the window for holiday bookings closed in September. They are wrong. In the loyalty program world, efficiency dictates that unsold inventory is worthless once the plane door closes. As a result, airlines and hotels quietly release a “second wave” of award availability between 14 and 3 days prior to departure.

I see this every year. While the general public pays $1,200 for a basic economy seat to fly home, savvy redeemers are booking that same seat—or a better one—for fixed point values. The key is ignoring the dynamic pricing algorithms designed to panic you into overpaying.

You aren’t looking for a “sale.” You are looking for a system inefficiency. Here are the three specific mechanics I am using right now to book 2025 holiday travel for pennies on the dollar.

Hack 1: The “Partner Shield” (Bypass Close-In Surcharges)

The biggest mistake you can make right now is searching for flights on United.com or Delta.com. These airlines use “dynamic pricing,” which means when cash fares skyrocket for the holidays, point prices skyrocket too.

In November 2025, United quietly increased “close-in” award pricing by roughly 33% for flights booked within 14 days of departure. A standard 15,000-mile flight often prices at 20,000+ miles. The solution is to use a partner program that still uses a fixed award chart.

Option A: United via Avianca LifeMiles (Best for Mixed Routes)

Avianca LifeMiles is a Star Alliance partner of United. They do not see United’s dynamic price surges. They only see “Saver” award space. If there is a seat available, LifeMiles charges a flat rate based on region.

The Math:

• Flight: Newark (EWR) to Chicago (ORD) one-way, Dec 23, 2025.
• United.com Price: 22,500 miles + $5.60 (Dynamic Surge Pricing).
• LifeMiles.com Price: 7,500 – 10,000 miles + $25 booking fee.
• Value: You save 12,500+ miles. Even with the $25 fee, the math is undeniable.

Option B: American/Alaska via British Airways Avios (Best for Short Haul)

For American Airlines or Alaska Airlines flights, use British Airways Avios. Their distance-based chart is unbeatable for short hops (e.g., NYC to DC or Miami). While American might ask 30k+ miles for a last-minute holiday flight, BA charges a fixed rate.

Note: Following the mid-2024 devaluation, the pricing is slightly higher but still beats dynamic pricing:

• Zone 1 (Under 650 miles): 12,000 Avios (vs 8,250 previously).
• Zone 2 (651-1,151 miles): 16,000 Avios.

How to Execute:

1. Go to United.com (or AA.com) and search for your route. Look for flights labeled “Saver Award”.
2. If you find a Saver seat, immediately go to LifeMiles.com (for United) or BA.com (for American).
3. Search the exact same route. You should see it for the fixed lower price.
4. Transfer points instantly from Amex, Capital One, or Citi and book.

Hack 2: The “Buy Points” Arbitrage (Hotels)

Buying points is usually a bad deal. However, during the holidays, cash prices for hotels often disconnect from reality. A Courtyard Marriott might ask $450/night, or a Waldorf Astoria might ask $1,500. This is the only time I recommend buying points speculatively.

Right now, Hilton Honors is running a promotion offering a 100% bonus on purchased points through December 31, 2025. This effectively lets you buy points for 0.5 cents each.

The Math: Ski Trip Example

Let’s look at a high-demand property like a Hilton near a ski resort or in New York City for New Year’s Eve.

• Cash Price: $800 per night (including taxes).
• Points Price: 80,000 points per night.
• Buying Points: You buy 40,000 points for $400 and get 40,000 bonus points free. Total cost: $400.
• Result: You pay $400 for a room that costs $800. That is a 50% discount instantly.

Pro Tip: Hilton gives you the “5th Night Free” on award bookings if you have Silver status or higher (which you get automatically with most Hilton credit cards). If you buy enough points for 4 nights, you get a 5-night stay, driving your cost per night down even further.

Check the official Hilton Buy Points Promo.

Hack 3: The “T-14” Premium Cabin Dump

If you have been hoarding points for a “dream trip,” the next two weeks are your golden hour. Airlines would rather fly with an empty seat than sell it for cheap cash, but they will release it to partners for miles at the last minute to get some liability off their books.

We call this the “T-14” window (14 days before departure). For some airlines, it is even tighter—T-3 or T-4.

Current Sweet Spots (December 2025):

• Lufthansa First Class: Lufthansa is currently releasing First Class seats to partners (like LifeMiles and Aeroplan) roughly 3–4 days before departure. You can fly Frankfurt to US East Coast for ~87k LifeMiles vs $12,000 cash.
• ANA Business/First: ANA often dumps unsold inventory on routes like Tokyo (HND/NRT) to Chicago or JFK roughly 14–21 days out. Book via Virgin Atlantic Flying Club for incredible value if you can find the space.

How to Automate This:

Do not search manually. Use a tool like Seats.aero. Set an alert for your desired route for “next 14 days.” You will get an email the second a seat opens. You must book immediately—these disappear in minutes.