It’s Not Too Late! Here’s How You Can Still Get Deals on Holiday Travel

United States Insider Guides
by Maren Engh Nov 15, 2021

Planning holiday travel is hard, not just because it’s a true “joy” to visit family. Season greetings come with the season’s highest prices, making it even harder to budget for. With travel industries on the mend after a devastating 18 months, prices for flights and hotels are fluctuating more than the latest crypto coin, especially the closer you get to the holiday season. Don’t get your tinsel tangled; there are still plenty of deals ready to unwrap. Whether it’s a family vacay or a tropical escape, here are a few of our favorite tips for hotels and flight deals this holiday season…as well as a few tips on what not to do.

Be flexible and track prices

As you may have noticed, flight prices seem to skyrocket when you most need to travel. Unfortunately, that’s usually because when you need to travel, it happens when everyone else does too.  Despite the increased demand, there are a few things you can do to find the best deal for your holiday travel.

First thing’s first: If possible, be flexible with dates.

I know, I know, asking you to be flexible as my first tip might make you roll your eyes, but truth be told, flight deals will rarely if ever, happen to occur on your travel dates. If you have flexibility within 5-7 days, you’re WAY more likely to catch the best prices. Consider ways you might be able to extend or even break up your trip. If your office lets you work remotely for a day or 2, you might be able to save hundreds by avoiding the busiest travel days and leaving mid-week.

The easiest way to look at flight prices within a general time frame is by going to

If you have a specific destination in mind, search your origin airport, such as Las Vegas, and your destination, such as Cancun, Mexico. Then select the dates, and you’ll see the calendar appear:

You can select different date combinations to see the lowest prices appear and find the best variety of days. From there, you’ll be able to select the flights and book directly with the airline or via a third party.

If you do not see the prices you want, you can sign up for alerts in the event the price changes. I have personally used this option many times and lucked out when prices go down:

If you’re looking for more general deals or are flexible on where you want to go, we recommend signing up for some of the flight-deal services, many of which are free. Here are some of my favorites:

Most of these free services offer paid memberships, but the free versions are still a great option and can help you track deals from your home airport when you sign up. I have landed some incredible deals through these services, like a $250 roundtrip direct flight from San Francisco to Barcelona, Spain, a few years back.

Check all the hotel sites before booking

Hotels, while fun to discover and book, can fluctuate just as aggressively in price. Whether you’re using cash or points, there are a few ways to find the best deals, even during holiday travel.

For cash bookings, I generally recommend searching for deals on first. This will allow you to see all the available hotels in that location and, typically, 3-5 websites with pricing. It’s extremely helpful if you’re trying to get the “lay of the land” and find the best hotel options. When you search through Trivago, you can see the different deals and select the best option for your budget. For example, booking the Hotel Riu Cancun is more expensive on Expedia than it is on Trivago is an easy way to price compare to make sure you secure the best deal.

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Photo: Trivago

Another recommendation is to take a look at wholesalers like or While Costco offers great deals to members, Luxury Escapes is a free site to sign up for and offers incredible luxury deals with several add-ons. For example, if you’ve been dreaming of your dream trip to the Maldives, but it’s never really been a reality, I have news for you. This might be your year. Check out the offers on Luxury Escapes that include the $500 transfer fees per person for free as well as meals and more. Take this deal, for example:

Mercure Maldives is a newer property in the Maldives, and at $600 per night in a private villa, all-inclusive for two and including the transfers from the international airport, it’s a great option, particularly when you’re comparing the prices to holiday travel in the Caribbean or even Mexico.

Wholesalers, like Luxury Escapes, can offer incredible deals at major discounts, even around holidays. Traditionally, these types of deals were only available through travel agents. However, times have changed, and now you have the opportunity to search, click and book a great deal without breaking the bank.

Yes, you have hotel points

If you have a specific destination in mind or are looking to use points, there are options for you too. The best deals will usually come from larger loyalty programs like Hyatt, Marriott, or Hilton. As long as there is a standard room available, you can book a room on points. During peak travel season, like the winter festive season, cash rates can be astronomical. However, points can save the day.

Take, for example, The Confidante, a Hyatt property in Miami. With rates over Christmas at almost $500 per night, booking at 15,000 points per night is an exceptional deal:

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Photo: Hyatt

Do you have a Chase Ultimate Rewards credit card? If yes, then you “have” Hyatt points, almost. Chase credit cards offer transfer partners across the travel industry, and one of the best values is Hyatt. You can transfer your hard-earned credit card Ultimate Rewards points to Hyatt at a rate of 1:1, meaning one Ultimate Rewards point = 1 Hyatt point. If you don’t yet have the Chase Sapphire Preferred, one of the most loved in the collection, the sign-up bonus on the Preferred is enough to get you four free nights at The Confidante right now.

Speaking of credit cards, using your credit card’s booking portals may also offer you some great options, particularly if you want to use points. While the points rates through credit card portals are affected by price, there may still be great options to use points or combine points and cash exclusively. American Express offers their Fine Hotel & Resorts program that includes a variety of extras, like complimentary breakfast, resort credit, and more. Similarly, they have thousands of hotels on their portal that you can book with both cash and points. Often, you’ll even find excellent offers, like “book three nights, get one free.” Similar to, search for your destination and dates, and you’ll see the cash and points rates. If you have points saved up and are trying to save your cash, this may be just the option for you.

What not to do

Do not, under any circumstances, book a non-refundable hotel room or activity. It’s one thing to deal with airline credits and use that later, but airlines are more regulated and therefore more flexible with their change fees and issues related to your travel bookings. Since last year, many hotels and hotel companies have taken a much harder stance and will not refund you, credit you, or change your booking if you book the non-refundable rate. While it may seem like a deal at the time, I highly recommend you stay flexible and book the refundable rate. That way, if the pandemic cancels your trip or anything else goes wrong, you can cancel your hotel without penalty.

One pro tip on that note, though, is that I always book the refundable rate. As I get closer to my trip, I’ll look at the rates again. If I know, for a fact, that I’ll make it (i.e., 1-2 days out), I will book the non-refundable rate at a discount and cancel the refundable booking.

The second thing not to do is use the wrong credit card. When you use the right credit card, like the Chase Sapphire Reserve or the American Express Platinum card, there is tremendous peace of mind. Why? Because those credit cards offer amazing travel isurance. Especially during the holidays, there are millions of travelers, and ultimately, anything can go wrong. You could lose your luggage, there could be significant flight delays causing missed connections…and the list goes on. Using the right credit card could save you hundreds, or thousands, of dollars if you need to spend the night in your layover city or buy supplies because the airline lost your luggage.

Lastly, do not miss the booking window if you see a good deal in your inbox after setting those alerts. Don’t second guess yourself. If you see the deal, grab it now. Flight and hotel pricing can change by the minute, and you may never see that price again.

Prices fluctuate, both high and low, and with enough persistence and strategy, you can find the right combination of flights and hotels for your needs. Be sure to sign up for flight alerts and check your credit card or hotel loyalty program accounts ASAP to make sure you score the best deals. Get ready to dust off that passport – happy travels!

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