How I Booked Two Southwest Round Trip Flights for $23

Or, “Why you should get the Chase Southwest Rapid Rewards card right now.”

Interrupting your regularly scheduled programming to share some humble-braggy news: I just booked two round trips to Miami for February for $22 and change. I’d be lying if I said I wasn’t super pumped about it. I’ve already had some people ask me how I did it, so I wanted to lay it all out below.

Let’s get this out of the way first. There’s no magical secret or crazy sale or mistake fare that brought flights down to $7. This was a combination of research, timing, flexibility, and effort.

I recently started doing more research on something called “travel hacking.” I kept seeing these crazy posts of people getting all sorts of flights & hotels for free. I just assumed it was too good to be true. That I would never have that kind of luck. It’s not too good to be true and there’s zero luck required. It takes some effort. But it is totally possible for anyone who wants to earn free travel. This is my first ever nearly-free flight. I started pretty small with a short domestic trip, but you bet I’ll be looking for how to score bigger & better flights from now on.

Here’s how I did it:

Step 1: I signed up for the Chase Southwest Rapid Rewards credit card.

Note: I’m not getting reimbursed in any way for writing about this card. I just love it and want to share my secrets. However, Southwest does offer points for referrals. So if you decide to sign up, use this link and we both get points. Help a girl out. Yay.

When I signed up a few months ago, they were running a promotion. It offered 40,000 points after you spent $1,000 in three months.

I’m not seeing this promotion advertised on the Southwest site anymore. But if you sign up using this link, you’ll still be able to get it. (If you don’t have a Rapid Rewards account with Southwest, sign up. It’s free & quick, and it’s where your points will accumulate.)

I started putting all of my everyday expenses (gas, groceries, etc.) on the card as soon as I got it. That $1,000 added up way faster than I expected. My 40,000 points posted to my Rapid Rewards account the same day of my second statement from Chase.

How much is 40,000 points worth? A $100 flight seems to be around 5,000 points as of the time this post is being written. So this bonus is worth around $800.

Step 2: I waited for a sale.

Waiting for a sale is crucial to maximizing your points spending and getting the most out of your 40k bonus.

Once my 40,000 points posted, it was time to shop. I have a week off from work in February, and I knew that’s when I wanted to travel. I had a few destinations in mind–New Orleans, Havana, Miami, and Cancun, but I wasn’t super picky about where I ended up going.

Flexibility is key here. If you absolutely have to go to a specific city on a specific date & time, you’re not going to get any good deals.

I researched the prices of Southwest flights to all of the destinations I had in mind for the dates I wanted. I originally wanted to travel Friday-Wednesday, but I quickly realized that a Monday-Friday trip had significantly less expensive flights no matter where I ended up going. (Flexibility, y’all.) I immediately ruled out Havana because the flights were expensive and inconvenient, but I was still stuck between New Orleans, Miami, and Cancun.

So I waited for a sale. Southwest runs “sales” fairly often. These sales don’t knock hundreds of dollars off ticket prices. The goal, I imagine, is to fill up the still-empty flights, which are the ones at awkward times or with annoying layovers. I believe the flight I bought was reduced by about $40. Nothing to write home about, but a great way to maximize my point spending.

I found a one-way 5:30 a.m. flight to Miami that cost $112, or about 5800 points. This was reduced from around $170, I believe. Early flights suck, but it’s definitely worth it. I found an equally early return flight for a little more. In total each round trip cost 12,550 points, plus about $11.50 each in taxes and fees.

I got two round trips for a total of 25,100 points and around $23. This leaves me with about 15,000 points of my bonus. Plus I have another 5,000 that I’ve earned over the last couple of years from flying Southwest. I still have enough in my account to book another round trip flight for free! I consider getting three round trips a great use of my bonus. It definitely makes it worth signing up for the Chase Southwest Rapid Rewards card.

Quick recap:

  1. Sign up for the Chase Southwest Rapid Rewards card using this link
  2. Spend $1,000 in 3 months and get 40,000 bonus points
  3. Be flexible about your dates & destinations
  4. Use sales to make the most out of your bonus points

It’s not magic. But it is a foolproof and simple formula to earn a couple of free vacations. Who doesn’t want that?

Have you ever scored amazing flight deals? Do you use the Chase Southwest Rapid Rewards card? Let me know in the comments. If you liked this post, be sure to follow me on Pinterest and Instagram for more.


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