Booking Southwest Flights

Lately, I luv Southwest.  I’ve had great service recently and plenty of good experiences with the carrier.  With my Companion Pass on the horizon, that is, if all goes according to plan, I’ll be flying them even more in the next two years.

Speaking of Companion Passes…I should have an update for you in the next week or two.  Fingers crossed!

With all the practice I’m getting booking Southwest flights, I thought a little tutorial might be helpful.  Southwest’s website is fairly user-friendly, in my opinion, but I hope this information is still helpful!

This post is especially timely, since Southwest is currently having a sale!  Book by tomorrow (June 9th), and fly from most of September to December.  If you don’t have time to book by then, don’t worry.  Southwest runs these sales all the time.  I try to wait until Southwest is having these “flash” sales to book domestic flights, as I know the next sale will be right around the corner.  Want to know when the next sale is?  Just sign up for Southwest’s emails, they’ll be more than happy to drop you a note!

Step 1:  Find your flights.


First, you obviously want to know which flights you want.  Simple.  Select your departure city, date, and arrival city.  Let’s fly to Baltimore.  How about September 21st?


If you plan on going back home, you can book a roundtrip, although, Southwest’s booking lends itself to one-ways in most cases.  We’ll look into that more in a future post, I’m sure.

For now, let’s just assume I’m flying one way.

Maybe I plan on flying home from a different airport, or driving home.

Step 2:  Select your flights.

Southwest will turn up a series of flights for the date and airports you selected.  Hopefully the price is good, otherwise, you can use the “low fare calendar” if your travel dates have some wiggle room.


Southwest’s flights from Boston to Baltimore on September 21st, 2016.

Once you select your date, it will bring you back to the flight results page.  Keep in mind that the lowest fare on the calendar may have a terrible connection or something else that makes it impractical.   Remember, there’s a reason it’s the cheapest flight.  Be sure that the flight offers you the best value, which isn’t always the cheapest ticket price.

BOS-BWI Calendar

The low fare calendar, great if you have flexible travel plans!  There’s not a whole lot of discrepancy in this example, but sometimes you can find a great deal by moving your trip forward or back by even one day.

You can select points or cash to pay your flight.  And by cash, I obviously mean a credit card that will earn extra miles on Southwest flights, or extra points on airfare booked directly with any airline.

Step 3 Book you flights (with cash or points)!

When paying up front for your flights, the price is easy.  For domestic flights, the total cost per ticket should come out to exactly the quoted price of the tickets.


BOS-PUJ Fee Breakdown

Boston to Punta Cana, the fees increase quite a bit…

When booking with points though, you’ll have to pay the points required plus any government imposed taxes and fees.  For domestic flights, this is a simple $5.60 per passenger per flight.  International flights typically incur steeper fees, as shown here.  Depending on where you’re going, airlines will add airport fees, arrival or departure fees, flight taxes, environmental subsidies, etc.  These fees will show up on any airline, since they’re dictated by the governmental agency or port authority figure at the location, and have nothing to do with individual carriers.  (Not to be confused with surcharges on partner award flights.)

I’m going to book with points, so I can cancel these flights later.  Even when I book with points or miles, I always price out the flights, so I can see the value I’m getting from my points.  Most folks value Southwest Rapid Rewards around 1.5 cents apiece, so anything at 1.5 or higher, I’m happy.  In my experience, I’ve been able to get closer to 1.8 cents per point.

Definitely a travel hacking win!

I hope some of you get some use out of this quick how-to!  It’s pretty straightforward, so you shouldn’t have any issues.  If you do, feel free to ask away, and I’ll do my best to answer!  I’ll be getting plenty of practice booking Southwest in the coming year and a half, so I’ll be sure to report back on any changes or updates to the system.

How to Cancel Southwest Flights coming soon!

You know, since I don’t actually have any reason to fly to Baltimore in September…


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