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Paid Business Expenses = Free Flights

And not just you, take a companion for free too!

Flying for free is one of my favorite things to do. It's easy too! Step one: get two new specific credit cards. Step two: pay your small business expenses with those credit cards. Step three: you and your companion get to fly to over 100 destinations in 11 countries -- for free. This step-by-step guide shows you exactly how to do it all.

Which airlines can I fly free?

The best one: Southwest. It's the world's largest low-cost carrier and flies to over 100 destinations in 11 different countries. It's also the only airline in the world that gives you a special Companion Pass that allows you to always bring someone with you -- for free! That includes your spouse, your child, a friend, or even a random person you just met. You can bring anyone you want. However, if Southwest doesn't fly out of an airport within driving distance, use this guide instead.

Why not American Airlines or Delta or any other airline?

Because none of those airlines give you a Companion Pass. When you fly on those other airlines, you pay more for a single ticket. With Southwest, you pay less and get two tickets. It's the best value in flying -- by far. Additionally, it lasts for two years! You get the benefits for the rest of this year, and ALL of next year. However, if you don't like Southwest, prefer to fly 1st class, or you really and truly prefer another airline, use this guide instead.

Ok, how do I get the Companion Pass? Let's goooooo!

As with everything, there's an easy way -- and a hard way. The hard way is to fly 100 or more paid one-way flights on Southwest in a calendar year. That's a whole lot of flying. If you don't have the time (or the money) for that, then I suggest you take the easy way and get two new credit cards instead. You'll need one for business expenses, and another one for personal spending.

What do I need to make this happen?

Business Expenses - The hardest part (which isn't actually hard) is having a business with expenses that you need to pay.
Good Credit - Ideally, you'll also have a 650+ credit score. You can successfully apply for these credit cards with lower scores, but you may need to go through the reconsideration process to do it.
Few New Credit Cards - You'll need to be under 5/24. That's a fancy way of saying that as long as you haven't received more than four new personal credit cards in the past twenty-four months -- you're good.
Two More Credit Cards - Last but not least, you'll need these two new credit cards:

#1. Southwest Rapid Rewards® Performance Business Credit Card

Summary: Less than 650 credit score? Get unlimited 1.5% cashback with a small annual fee that you'll make back.

This card has an annual fee of $199. It's so worth it. First, they give you 9,000 free points each year (worth $123). Next, they give you four upgraded boardings each year (worth $120). But wait, there's more. You also get free Global Entry or TSA PreCheck (worth $100) so you can skip those long security lines at the airport. And last but not least, they give you free Wi-Fi on every single flight. That's right. You'll never have to pay for Wi-Fi on a Southwest plane again. They give you waaaaaay more value than the annual fee. So essentially -- they're paying you to have this credit card.

#2. Southwest Rapid Rewards® Priority Credit Card

Summary: 650+ credit score? With unlimited 2% cashback, this is the best pure cashback card.

This card also has a high annual fee, but once again -- they're actually paying you to have this card. Here's the math. Chase charges you $149 per year to have this card. However, they also give you $75 to spend on flights, so that brings the cost down to $74. But wait, there's more! They also pay for four upgraded boardings that let you board before almost everyone else, at a cost of $30 each. After that $120 in credits, they're paying you to have this credit card. There are even more benefits to this card like getting 7,500 free points (worth $96) every year and 25% back on inflight purchases -- but none of that matters, because they're still paying you to fly Southwest!

Oh, I almost forgot to mention that both of these cards come with substantial sign-up bonuses. That's the real reason that you need both of these cards. The sign-up bonus points count towards your Companion Pass qualification. To qualify, you need 125,000 points. With these two sign-up bonuses -- you qualify! Because Chase has rules that limit the number of credit cards you can get in a 24-month period, make sure you get the business credit card first. After that, get the personal card. Remember though, you need both credit cards.

You got it! Once you qualify for the Companion Pass with 125,000 points from your sign-up bonuses and initial spending, you actually have:

Year #1:

125,000 points x 1.37 cents = $1,712.50 in free flights
$1,712.50 + $75 flight credit = $1,787.50 in free flights
$1,787.50 x 2 from the Companion Pass = $3,575 in free flights

Year #2:

7,500 anniversary points + 9,000 anniversary points = 16,500 free points every year
16,500 points x 1.37 cents = $226.05 in free flights
$226.05 + $75 flight credit = $301.05 in free flights
$301.05 x 2 from the Companion Pass = $602.10 in free flights

You get a minimum of $3,575 in free flights on Southwest, and $602 in additional free flights the next year, just by signing up for two new credit cards and paying your normal expenses. So to recap:

The Southwest Companion Pass is the best value in flying.
Once you have the pass, you can take anyone you want with you on every Southwest flight.
You'll have the Companion Pass for the rest of this year and all of next year.
You need the sign-up bonuses from both of these credit cards to qualify for the Companion Pass.
The sign-up bonuses and anniversary points give you and your companion $4,177.10 worth of free flights with very little effort.
They actually pay you to have both these cards with $100's in useful credits.
You get to board before most everyone else.
You get free Wi-Fi.
You get free Global Entry or TSA PreCheck.
You save 25% on everything you buy in-flight.
There are even more benefits to list but I'm running out of words.
You're welcome.