How to Get Cheap Flights on Southwest Airlines

My “go to” airline for family travel is Southwest Airlines. Their rates are very reasonable and affordable and their customer service personnel are extremely helpful. In addition, their flight crews are pleasant, and they are rarely late. Because I have an airport nearby that is serviced by Southwest Airlines, our family uses them to travel often. In the last ten years, our family has used both the Chase Sapphire Preferred credit card and the Southwest Rewards credit card to help pay for the cost of flights. In addition, I have also found some ways to maximize the point value and get Southwest flights for cheap.

How to get cheap flights on Southwest Airlines

The Southwest Airlines rewards program is fantastic and you can redeem miles for very little. In fact, we have even scheduled impromptu trips (our Nashville trip) based off of what was on sale or what was the cheapest to be redeemed. I started off by getting the Chase Southwest credit card a few years ago. With the generous 50,000 mile sign up bonus, it was enough to get my family of 4 somewhere in the country for free. We traveled to Seattle and took a road trip around northern Oregon. I canceled the card before the first year was up because I found more value in the Chase Sapphire (that annual fee was about $80 too).

Check out: How to Find Cheap Flights to Europe

Transfer Points on Credit Cards

Here is what I do very often: I transfer my Chase Sapphire points and convert them into Southwest miles. This simply requires entering your Southwest Airlines Rapid Rewards number and pressing a button (very easy to do on the Ultimate Rewards portal). Since I charge most of my spending on my Chase Sapphire credit card, I have thousands of points in just a few months. We usually travel somewhere “big” in the summer, so I try to save points for that trip, and make all my purchases on my Chase Sapphire card, accumulate the points, and transfer it over to Southwest (by the way, the points transfer instantaneously). If we don’t have enough points for all 4 of us to travel to the destination, at least some of us would travel for free and the others pay. This is still a pretty big discount.

To read more about how I use the Chase Sapphire Preferred credit card to travel cheap, click below on my two earlier posts:

How to Use Credit Cards to Save on Family Travel

Smart Ways to Use Your Chase Sapphire Credit Card


Check out: How to Find Cheap Flights from Travel Bloggers

When to Book a Southwest Airlines Flight

Every now and again I look at the Southwest app and when there is a sale going on I find a cheap destination and just go! I have found one-way flights for 2,000 miles!!! (like this Weekend in Nashville or 4 days in Baltimore and Williamsburg). However, what I usually do is book with plenty of anticipation (what can I say… I’m a planner).

Since we usually have a big trip in the summer, I buy my family’s tickets when Southwest comes out with their flight schedules around November/December. In the summer (around June), they release the flights for December (my holiday trip). Therefore, I plan for the summer trip the November before, and I plan for the winter trip, the May before. By booking it literally the morning the flight schedule is released, I get better availability and schedules. You can check when the flight schedules are released by doing a simple Google search.

Southwest Airlines Boarding Process

Some people gripe that this is their “issue” with Southwest Airlines. I have no problems with it… again because I am a planner. 24 hours before the flight (exactly) I check into Southwest and get our seats. The day I book the flight, I set a reminder on my phone to alert me (exactly 24 hours before the flight). I make sure to have all the confirmation numbers ready and then check the 4 of us in.

We almost always get an A boarding. We have gotten B before and still always end up together – it has never been a problem. My kids are now too old for it, but when our daughter was 5 we could use “family boarding” which was after A and before B groups. You could also pay $15 one-way to guarantee that you will be an A boarding – it is called Early Bird Check-In.

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Bottom Line

To me, Southwest is the BEST airline for reward travel. It is even better when you have the Chase Sapphire credit card and can transfer those points over to get even more discounts on the flight price. To check out other ways I save money on travel, click below:

Best Cash Back Apps

How to Save on Your Car Rental

How to Get Free Hotel Stays

Five Easy Ways to Save Up for Travel

Travel Hacking E-Book

I recently wrote a short 25 page e-book that highlights our how our family uses credit cards to travel for cheap. It is a step by step guide for beginners who would like to know more about how to use credit card sign-ups to gain points and convert them into free flights and hotel stays. Our family started using this method a few years ago and it has dramatically changed how we travel. I encourage you to give it a read – How to Start Travel Hacking. Use code TLZ908AP47 for 24% off.

e-book cover

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