How I just booked tickets for 4 to Orlando for $30

You might not believe it, but its true.  We’re headed to sunny Orlando later this Spring to celebrate my brother-in-law’s graduation from high school.  No, he’s not from Florida, but why not celebrate there, right?  Especially if I can get there for $30.

English: Orlando Skyline at night

Orlando Skyline at night (Photo credit: Wikipedia)

You’re probably thinking, Sheldon, you simply forgot two more 00’s on the end of the $30, which would make the trip $3000.  No.  You heard me right.  I’m simply paying $30 for booking tickets for 4 to Orlando, Florida.  I’m pretty stoked about it.

Ok.  I’ll be honest.  There is a little bit of cheating here.  The fourth person is a lap child, so I really booked the trip for three people and a lap infant, but regardless it’s a smoking deal.  Let me walk you through the process.

Why I picked Southwest Airlines

We’ve talked about Southwest being one of the best domestic airliners for a variety of reasons:

  • They offer peanuts (and they’re free)
  • They allow 2 checked bags to fly free
  • They allow for changes to your itinerary
  • They are the most generous on award travel within the USA
  • They found a way to make the safety video at the beginning of their flights interesting

I booked the flights to Orlando on Southwest with full confidence knowing that If needs be, I will be able to adjust the itinerary to other flights if for some reason these dates won’t work for me.

Booking the Tickets for 4 to Orlando

You really want to watch the dates carefully with Southwest because their sales come and go.  Upon shopping their flights I found a gem out there that only took 40,000 Southwest Rapid Rewards to pay for the three flights.

Booking Southwest

This Itinerary Made Me Happy

I booked this flight about 4 months before departure and the availability was amazing.  We picked the best flights with the shortest travel time between destinations, which leaves me with the least amount of time chasing children.

I’ll keep my eyes peeled from now until departure, because if for some reason they drop the points requirements for this flight I’ll simply cancel the old reservation and rebook the new one at the lower cost.

Here is a quick YouTube video if you need some help (Click playlist in the upper left and go to video #7):

How to Get your Hands on Some Rapid Rewards

The easiest way to get your paws on a serious amount of Rapid Rewards is to score the Chase Southwest Credit Card.  They actually have four versions of this card, two personal cards and two business cards.  Be patient an make sure you get at least 50,000 as a sign on bonus for picking up one of the four versions.

Transfer Ultimate RewardsA little over a year ago I picked up the Chase Ink Bold card the offered a bonus of 50,000 Ultimate Rewards after meeting a minimum spending requirement.  The card has paid of handsomely with 50,000 Ultimate Rewards, but in a little over a year I’ve been able to build up a stash of up to almost 90,000 points (Muchas gracias 5 points per dollar on many categories).  If you’re interested in transferring UR to airline points you can check out this post.I quickly transferred the points from my Chase card directly to my Rapid Rewards account, and they transferred within about 10 minutes.

It doesn’t matter whether you use the Southwest card, or an Ultimate Rewards earning card like the Sapphire Preferred, Ink Bold, or Ink Plus you should get one and start putting some points on the board.  If you love to travel, you’ll find a way to use them.  My Ultimate Rewards just got me tickets for 4 to Orlando for $30, and you can do the same too.

Come On, Just WorldWanderlust With Us

Whether you’re new to the site, or you’re an avid follower, you know that we encourage people to go more new places every year.  Doing so will enrich your lives with experiences whose value far exceeds that of money, gold, or silver.  Spend the time now making memories with those you love.

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10 Responses to How I just booked tickets for 4 to Orlando for $30

  1. Tyler Christesnen says:

    So uh, you take your brother-in-law to Orlando…. And your actual real live blood brother? What about him?

  2. Ken says:

    Are you going to manually check SW flights for reductions or is there some tool you use? We’ve got quite a few trips this summer as positioning flights for int’l travel and any savings would be helpful.

  3. Laura Beck says:

    Sheldon, we just came back from Orlando, we did use our Southwest Airlines and all four flew for 30$ too! We stayed at Art of Animation Disney resort, we loved it, they have some cool benefits just by staying there. Weather was amazing too

    • Sheldon says:

      Nice Laura!! I saw lots of pictures on FB. It looked like you had a lot of fun. Hopefully we survive the trip. We are glad that you went for $30. Always puts a smile on my face! I am sure Collin was stoked about it too!

  4. Judd says:

    Hey Sheldon or Brad, have you applied for both the Chase business cards and the non-business card? I technically have a small business and would like to get at least two Chase Ink cards. Thanks for the input fellas!


    • Sheldon says:

      I can’t imagine why they wouldn’t let you get all of them. You will have to space them out, but I believe that Brad has scored all three of those cards himself.

  5. Spring says:

    Has anyone used this lately? If so, how do you know when they offer 50k points at signing up? I’m assuming you need to use the “wanna get away flights”, but looking at the schedule, there is only one red-eye (sorry, I don’t like the idea of flying with three small kids on a red-eye, especially since I’ve tried, and I can never sleep on a plane) that is listed as wanna get away. Is there a trick to when the wanna get away flights are listed?

    • Sheldon says:

      Spring- Great question. Since I made this post SouthWest decreased the value of their miles. It now takes about 15% more miles to travel places than it used to. Bummer. That is a perfect example why points-hoarding isn’t the best idea.

      Yes. You need to use the “Wanna get away” flights When using points you may need to be flexible on your dates in order to get better flights. Make sure you click on the “Flexible Dates? Search the low fare calendar.” That way you can find all of the flights that will use less miles for your destination and find one that doesn’t require taking a redeye.

      Does that help?

  6. spring says:

    Yes, that does help, thank you. I may not be able to fly for $30, but if I can knock the price down some, that will be a big help. Thanks again!

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