Spend Less on Winter Break Flights With Southwest Airlines by Preparing Now

Quick summary

Southwest has extended its booking window, allowing reservations through Jan. 5, 2020, making it possible to secure flights for major winter holidays.
Booking early is recommended to access the best prices, especially for peak travel dates like Christmas and Thanksgiving.
Southwest offers flexible change and cancellation policies, letting travelers rebook at lower prices or cancel with minimal risk.
Travelers can use loyalty points or travel credits, and the Companion Pass benefit allows a companion to fly for only taxes and fees if added while seats remain.

What to consider

Travel credits from fare differences are nontransferable and expire 12 months after the original booking date.
Points bookings are fully refundable, with points returned to the original account if plans change or prices drop.
Adding a companion with the Companion Pass requires at least one seat to be available on the flight.

What you'll miss from the article

Detailed guidance on leveraging Southwest's flexible policies, loyalty points transfers, and optimal booking strategies for peak holiday travel.

Generated by AI with support from our editorial team.

Update: Some offers mentioned below are no longer available. View the current offers here.

If you have yet to book your Christmas or other peak winter holiday vacation flights and want to score the best deals, there is still time — if you’re a Southwest customer. Although some carriers allow you to book 330 days in advance, Southwest is one of the airlines that extends its booking window in batches only a few months at a time.

As of this morning, Southwest extended its reservation schedule to book flights through Jan. 5, 2020. This means run — do not walk — and go book your Veterans Day long weekend, Thanksgiving and Christmas holiday flights now. (Previously you could only book flights through Nov. 2, 2019.)

The Christmas to New Year’s week is one of the most popular times of year for families to fly, so booking the moment the Southwest schedule gets extended is important. Although availability will (probably) still be around for a little while, the best prices will most likely be had today, especially for those peak travel dates. Southwest has an extremely flexible change and cancellation policy so if you book now and find a lower price at a future date, you can “rebook” your flight at the lower price. Here are the rules for the latter scenario:

If You Paid for the Flight: You will receive a Travel Fund credit for the difference in the fare price. You have one year from the date you initially booked the flight to use the credit. Travel Fund credits are nontransferable and can only be used for the same passenger.
If You Used Points for the Flight: The difference in points will automatically go back into the account from which those points were originally deducted if you reprice the flight.

This means if your family's travel plans change, you can cancel your flight with no cost and if the price decreases, you'll receive the difference back one way or another. This is a very low-risk booking situation, which is important for family travel.

Score the best deals on Southwest winter break flights:

1. Book Right Now!

I recommend booking flights immediately when the booking window opens. This already happened around 9:30am ET this morning, so you are still within the realm of being able to get a good deal (relatively speaking). As mentioned above, there is minimal risk with booking Southwest flights due to their flexible policies, so even if you are not 100% certain of your plans, book now — especially if you are using points. Southwest also allows you to cancel a flight within 24 hours of booking and you'll get a full refund. So go book your flight and then sleep on it overnight. If it is a paid reservation just make sure to cancel within the 24-hour timeframe. Note: If using points, your reservation is always fully refundable.

2. Transfer Points from Chase Ultimate Rewards to Southwest

Using Southwest points is my preferred method for booking a Southwest flight because of the airline’s flexible policies. If you need to cancel a flight booked with points, there is absolutely no penalty and your points go straight back into your Rapid Rewards account (you can cancel up until 10 minutes before the flight’s departure time).

If you do not have enough points in your Southwest Rapid Rewards account, you can transfer points from your Chase Ultimate Rewards account via cards such as the Chase Sapphire Preferred Card or Chase Sapphire Reserve (1:1 ratio). Although this might not provide you with the absolute best value for your Ultimate Rewards points, it is still a great option to secure holiday flights.

First, you'll need to link your two accounts, which only takes a minute or two. Log in to your Chase Ultimate Rewards account and go to "Transfer to Travel Partners." Scroll down to the Southwest Airlines Rapid Rewards option and select "Transfer Points."

You'll need to select the recipient and enter your Southwest Rapid Rewards number. While you can transfer points to one authorized user on your account (who is also a household member), you'll need to re-enter their information every time when initiating a transfer. After you click the "Continue" button, your information will be saved in your Frequent Travel Programs, even if you did not actually transfer any points.

Then, hover over the Southwest Rapid Rewards box and click "Transfer Points". Enter the number of points you want to transfer over, click "Continue" and then confirm the transfer. Note: Points must be transferred in 1,000 point increments.

3. Use a Companion Pass, But You Can Add it Later

The Southwest Companion Pass is my favorite benefit in the travel industry. You’ve probably read about it before on TPG, but it ultimately allows a friend or family member to fly with you for free (plus taxes/fees) for the life of the pass. Normally, the pass expires Dec. 31 the following year after you earn it (though sometimes promotional passes only last for one year).

If you do not yet have the pass but you are planning on earning it this year, you can still book your Christmas vacation flights now and then add your companion’s ticket later. The only requirement for adding your companion onto your reservation is that there must be at least one seat left for sale. Since Christmas is an extremely busy time of year, there is the chance that your flight will sell out if you wait too long.

Remember, welcome bonuses and credit card spending from all four cobranded Southwest credit cards count toward the 125,000 qualifying points needed in a calendar year to earn the pass. These include: Southwest Rapid Rewards Plus Credit Card, Southwest Rapid Rewards Premier Credit Card, Southwest Rapid Rewards Priority Credit Card and Southwest Rapid Rewards Premier Business Credit Card. All three personal consumer cards are currently offering 40,000 points after you spend $1,000 on purchases in the first 3 months from account opening.

4. Have Alternative Dates in Mind

If you have some flexibility for your holiday travel, use that to your advantage when booking your flights. The most expensive day to depart for your Christmas vacation this year will probably be Saturday, Dec. 21. If you can shift your dates one or two days before or after, you might find the price to be significantly less (although Friday and Sunday will still be expensive). If you want to book the least expensive dates, leaving for your vacation early on Dec. 18 or 19, or waiting until Dec. 24 or 25, might provide a decent amount of savings. Of course, those dates might not work for all families, but having backup dates might pay off.

5. Watch Prices, and Request a Credit

If your flight happens to go down in price between when you book and when you fly, you can easily get the difference in Rapid Rewards points back into your account. Of course, these flexible policies still exist when you pay for your fare with cash, but you'll end up with a nontransferable Southwest credit instead, which expires 12 months after your original booking.

Christmas Flight Options

Here are some samples fares I came across. With this extension window, being flexible is key.

Ft. Lauderdale to Cancun

If you are willing to fly out on Christmas Eve, you can enjoy Cancun or the surrounding area for just 6,000 Southwest Rapid Reward points! If you are looking to use your World of Hyatt points, I am still seeing availability for most (although not all) dates at the Hyatt Ziva Cancun.

Oakland to Honolulu

With Southwest now flying to Hawaii, you can fly to Honolulu for 13,000 Southwest Rapid Reward points. Just leave a few days before school departs and you'll get a great deal.

Providence to Ft. Lauderdale

For those in the Northeast that are looking to get out of the potential snow and cold this upcoming winter, head to South Florida for less than 18,000 Southwest Rapid Reward points. And that is on one of the most peak days of the year.

Bottom Line

Knowing the ins and outs of booking a Southwest flight can allow you to book the best flights possible for your family at the lowest cost. I personally was able to snag semi-good fares to the Caribbean for my family, although Wanna Getaway Fares were pretty nonexistent for peak dates. Congrats to those who are able to snag some good fares.

Jennifer Yellin covers family travel deals for TPG and blogs at Deals We Like. Follow her family’s adventures on Twitter and Instagram.

Update: Some offers mentioned below are no longer available. View the current offers here.

If You Paid for the Flight: You will receive a Travel Fund credit for the difference in the fare price. You have one year from the date you initially booked the flight to use the credit. Travel Fund credits are nontransferable and can only be used for the same passenger.
If You Used Points for the Flight: The difference in points will automatically go back into the account from which those points were originally deducted if you reprice the flight.