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How to Book a Holiday-Weekend Getaway on the Cheap

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You may find yourself disappointed, defeated and disgruntled if you give flight and hotel award availability for holiday weekend dates (or other peak travel periods) a quick glance. Of course everyone wants to fly out Thursday or Friday and fly back Monday, which means there are no available award seats — at least not at Saver or low levels. Today, I’ll discuss some strategies that allow for cheap travel on these peak dates and give the example of how I booked a last-minute trip for my family of four over the Columbus Day weekend.

The Challenge

When I searched for awards on American or United out of the DC area for Thursday and Friday on Columbus Day weekend, I found little availability. For many flights departing from DCA this past Friday, American was asking 50,000 miles for an economy seat — including on many regional flights less than two hours long. Please do not use your American miles in this manner.

The economy award calendar looks like this for AA flights out of DCA on the Friday before Columbus Day weekend.
The economy award calendar looks like this for AA flights out of DCA on the Friday before Columbus Day weekend.

Checking options from United’s Washington Dulles hub, I found only a few routes offering Saver economy seats on either Thursday or Friday before the Columbus Day weekend. A solid blue line on the dates below indicate Saver economy space available. There was some Saver first availability, but I don’t recommend using your United miles for a domestic first-class flight unless it’s a transcon or a flight to Hawaii.

United award routes out of IAD don't fair any better than what American is offering.
United award routes out of IAD didn’t fare any better than what AA offered for Columbus Day weekend.

These patterns for Saver and low-level availability for holiday weekends repeat themselves regardless of the airport you call home or the route you want to fly. My searches for return award flights on the holiday Monday looked the same. Considering this, you might think the logical solution is to pay for a flight over the holiday weekend. However, you’ll encounter sky-high prices, especially if you want to leave Thursday night or Friday morning and return Monday to maximize your weekend away.

Looking at hotel award availability and hotel prices for holiday weekends will lead to the same disappointments. So with seemingly dismal options for both hotel award nights and low-level award flights, how can you travel for cheap on holiday weekends?

The Tools

I used the below tools to book a cheap weekend trip to the Berkshires. Photo courtesy of
I used the tools below to book a cheap weekend trip to the Berkshires over Columbus Day weekend. Image courtesy of Shutterstock.

Let’s look at what tools you should have in your proverbial travel belt to combat paying high award or revenue prices on holiday weekends:

1. Transferable Points — As the popular sports idiom goes, the best defense you can have is a good offense. The best thing you can do to defend against paying high award prices or finding no hotel availability is earning transferable rewards points across a few different programs. This gives you options for multiple hotel chains and airlines. If you only earn AAdvantage miles, you have no defense against the prices listed above.

2. Points Allowing Revenue Redemptions — A few loyalty programs allow you to redeem your points toward revenue airfare at a value of more than 1 cent per point. This means you can find the cheapest airfare possible and then use points to cover that cost, while having the flight count toward elite status and earn you redeemable miles. You can redeem Citi ThankYou points for 1.25 cents apiece toward airfare on any carrier, while Citi Prestige cardholders can redeem points for 1.6 cents each for American Airlines tickets and 1.33 cents each on other carriers (until next year, at least). Wells Fargo Visa Signature cardholders can redeem points for 1.5 cents each toward airfare; Chase Sapphire Reserve cardholders can redeem Ultimate Rewards at 1.5 cents each toward travel; and those with the Chase Sapphire Preferred can redeem points at 1.25 cents apiece toward travel.

It’s also worth earning points in programs where the points are tied to the revenue cost of the ticket and there aren’t black-out dates for awards. JetBlue, Southwest and Virgin America come to mind. While the ticket will cost a lot of points if the cash price is expensive, you can still get free seats, or at least one free seat so you only have to pay for your travel companions.

3. Revenue Cost Minimization Tools

If you know award seats are going to be tough (or impossible) to come by, take measures to ensure you’re paying as little as possible for revenue tickets. Here are a few tools I suggest you gain access to and monitor/utilize regularly:

  • Amex Offers Amex Offers are opt-in, limited-time, targeted offers for Amex cardholders. It’s worth regularly reviewing all the options for each of your cards on the Amex website, as several travel companies have deals listed.
  • Bank of America BankAmeriDeals — Just like Amex Offers, these are limited-time, opt-in, targeted offers for Bank of America cardholders. October offers include 5% back on Airbnb bookings and 10% back on Hampton Inn bookings.
  • Discount Airline and Hotel Gift Cards — You can buy unused gift cards from resellers all over the internet, oftentimes at significant discounts. While you have to be careful of which sellers you buy from, as you need to make sure you have protection in case of a “bad” gift card, taking advantage of sales from these sites can save you money and potentially earn you bonus credit card rewards. I recommend buying cards from Paypal Digital gifts with your Chase Ink Plus Business Card as you’ll earn 5x points and they regularly have sales. is also a recommended reseller. I find myself stocking up on gift cards from time to time at a discounted rate which makes my purchases of holiday weekend airfare and hotels sting that much less.

The Solutions

Taking the above challenges and tools into consideration, let’s look at how I booked a highly subsidized last-minute family trip to the Berkshires over Columbus Day weekend. The trip was for myself, my wife and our two children, both under two years old (meaning they meet the lap-child qualification).

JetBlue from Washington, D.C. (DCA) – Hartford (BDL)
Retail: $356
Paid: 23,400 points + $11.20 (points earned by completing the JetBlue/Virgin America match promo)

American Airlines from Albany (ALB) – Washington, D.C. (DCA)
Retail: $382
Paid: 15,000 Citi ThankYou points + $142 (with possible upgrade due to my Executive Platinum status)

Alamo Full-Size Car Rental
Retail: $175 (comparable rates on Amex Travel, Chase Ultimate Rewards portal and the car rental agency sites)
Paid: $114 all in via Costco Travel

I saved $80 by booking a hotel through Amex Travel.
I saved $80 by booking a hotel through Amex Travel.

One-Bedroom Mountain Resort Suite, 3 Nights
Retail: $601.44 from the resort’s site
Paid: Found for $502 on Amex travel + Amex Offer for $80 off $500 or more spent at Amex Travel = $422

Total Trip Retail Price: $1,514.44
Paid: $689.20 (55% off)

Bottom Line

As you can see, it’s possible to save on last-minute travel over a holiday weekend using a combination of points, miles and travel offers. I could have lowered the cost of our trip further if I had used more Citi ThankYou points to make our return flight completely free, but I like to subsidize these types of trips down to a level I’m comfortable with and stretch my points further. I also could have booked a single, standard hotel room at a cheaper property, but with two babies we really enjoy having a separate bedroom with a closed door during nap time and at night after we put them to bed.

Having a diversified portfolio of reward points in your pocket while taking advantage of cash-saving measures is a quick way to find yourself on a cheap weekend trip, even during a holiday.

What strategies do you use for cheap travel on holiday weekends?

Featured image courtesy of Shutterstock.

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