$1800 in flights to Disney World for less than $250 out of pocket

Southwest Rapid Rewards
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We live in Orange County, California and have Disneyland in our back yard, but our family and another family decided to check out Orlando for the Disney and Universal theme parks, especially the opening of the new Harry Potter world.  There are 3 of us in my family and our friends have 4 in their family.

We’ve been traveling using miles and points for years and years.  Their family has just started earning miles, but has yet to take a huge money-saving trip where the real value of miles and points shines through… this is that trip for them!

Orlando Trip Details

How much did the flights cost?

(When my friend booked his family’s flights, I didn’t take a screen shot, but these flights approximate his point usage and the out-of-pocket amount that he would have had to pay if he didn’t use points.)

Using points, each ticket cost 26,438 Southwest Rapid Reward points and $11.20 in taxes, for a total of 105,752 and $45.

Southwest SNA to MCO roundtrip points

If he had to pay cash for these tickets, that would have been almost $450 per person!  For a family of 4, that would be $1800!!!

Southwest SNA to MCO roundtrip cash

Using Southwest Rapid Reward points saved him $1755… but there’s another cost that we haven’t factored in yet that is associated with earning all of these points.

How did he earn the points?

My friend knows that my family and I fly all over the United States using Southwest points.  He has shown an interest in learning how to travel, so I shared with him a few best practices in traveling for pennies…. while everyone else pays full price!

There is a Chase Southwest credit card offer that provides 50,000 points for each of the business and personal versions of their cards.  He applied for each version… one for his personal expenses and the business version for his side business for when work is slow.

Combined, he earned 100,000 Southwest Rapid Rewards points for opening the cards.  In order to earn those points, he had to pay a $99 annual fee for each card and spend $2,000 within 90 days on each.

Reasonable concerns

Before he applied, he had three main concerns…

First, how would this affect his credit?  This concerns everyone… your credit score is something that you should protect at all costs because it can affect your employment, your ability to rent an apartment or buy a home, insurance rates, and so many other factors in life.  When you apply, your score will drop 3-5 points for every inquiry, but this impact is temporary and is quickly offset by the positives of having more credit available.

Second, he had the belief that you shouldn’t pay an annual fee.  I totally agree that paying annual fees are lame!  However, when you look at the value you receive, it makes sense.  I asked him, “If I could fly you and your family to Orlando from California for $250 vs. $1,800, would you take me up on that offer?”  Of course, you would!

The second reasonable concern that he had was being able to spend $4,000 within 90 days.  That is totally understandable… but when you put your gas, food, groceries, utilities, cell phone, car insurance, and other types of bills on your card, it doesn’t take much effort or time to reach $4,000.

Approved and earning some points

After spending $2,000 on each card, he now had 104,000 Southwest Rapid Reward points.

If you’d like to receive the promo code for the Chase Southwest 50,000 point offer, please complete this form, and I will send you the steps and offer code via email.  The current offer expires 9/30/2014, but I usually receive several promotions from them each year.  (Please note that Southwest will give me some points for referring you to them.)

How he took an extra step and earned $900 in additional flights

Since my friend had already earned 104,000 points, he was only 6,000 points away from earning the Southwest Companion Pass!  This benefit of the Rapid Rewards frequent flier program is my favorite across all airlines.  Whether you are using points or cash to buy your ticket, your designated companion can fly for free (just paying taxes) anywhere you fly when you’re on the same flight.

Southwest Airlines Companion Pass 2015 BaldThoughts.com
We’ve already earned our 2015 Companion Pass!

So, my friend spent the necessary $6,000 over the next couple of months so that he could have the Companion Pass.  When he earned it in March of this year, he not only receives the benefits for this year, but also for the ENTIRE year next year.  This benefit is not on a rolling 12 months, like some other airline and hotel benefit programs.

Once he earned the Companion Pass, he designated his wife as his companion.  With that, he was able to book her ticket to Orlando as a companion ticket, then cancel the ticket he originally bought for her.  This returned 26,438 points back into his account… using Southwest Wanna Get Away fares, those points would allow him to book a ticket for about $450 AND bring his wife with him for FREE… resulting in $900 in future flights for the happy couple!

PLUS, his wife is flying with him for free to Orlando now, so really that’s another $450 in flights for free because he earned the Companion Pass.


With the personal and business versions of the Chase Southwest credit card, my friend was able to save almost $1,600 in airfare from California to Orlando.  His flights would have cost $1,800, and he’s flying for free after using some Southwest points, paying about $50 in taxes, and two $99 annual fees.  As a bonus, he and his wife will be able to take another $900 in flights sometime this year or next!


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