Free Flights: 5 Ways I Maximize Earning Potential With Southwest Airlines

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I’m a big fan of Southwest Airlines for many reasons. Whether it’s the family-friendly attitude, the free checked bags, the whimsical heart-themed marketing, or flexible change policies, there’s something appealing about Southwest for almost everyone.

Personally, I love flying Southwest for the flexibility of changing or canceling my travel at any point, picking my own seat, and booking cheap award flights for spontaneous getaways. In fact, I book flights on points almost four times as often as I pay for Southwest flights in cash, according to my travel history over the last ten years. 

Here’s how I book more than a dozen free flights each year on Southwest.

1. Sign Up For a Southwest Frequent Flyer Account

I’ve been a Southwest Rapid Rewards loyalty program member for the past 15 years. By taking three minutes to fill out an online form, I’ve been able to earn points on every single cash flight I’ve taken since then, including for travel paid by my employers. And because I have an account for those points, I’ve been able to book several hundred free flights through the years - yes, really. 

While this may sound like an obvious tip, you’d be surprised how many travelers never bother to claim points they’ve already earned - myself included, prior to 2007. Even if you only fly once or twice a year, those points will add up - and since Southwest points never expire, you can keep saving them until the right time. 

And of course, having a loyalty account with any airline makes it easier to keep track of your boarding pass, Known Traveler Number for TSA PreCheck and Global Entry, and more. When I book a Southwest flight, my boarding pass automatically appears on my account so I can skip the check-in desk at the airport and go straight to the priority security line. In fact, I make it a game to see how quickly I can get from the airport curb to my flight gate; my current record is 3 minutes, and 12 seconds at my home airport. 

2. Hold a Credit Card That Earns Rapid Rewards Points

I earn almost all of my free travel by paying for everyday expenses with a credit card that earns travel rewards. Not only do I earn between one to five points on every dollar I spend, but I’ve also earned multiple sign-up bonuses for meeting certain spending requirements within the first few months of holding each credit card. 

Southwest Rapid Rewards® Plus Credit Card

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Secure application on issuer’s website

• Our Rating 4.0/5 How our ratings work
• APR20.99% - 27.99% (Variable)
• Annual Fee$69
• Sign Up Bonus $400 statement credit + 40,000 pts.Southwest Rapid Rewards Points More Info

  Earn a $400 statement credit and 40,000 bonus points after spending $3,000 on purchases in the first 4 months from account opening. Dollar Equivalent:

This is a great starter card for infrequent domestic travelers who want to earn rewards toward discounted Southwest flights without a huge annual fee. You won't get a ton of perks compared to other Southwest cards, and this card does charge foreign transaction fees so probably isn’t best for international travelers.

• Overview
• Pros & Cons

Overview

This is the entry-level card for aspiring Rapid Rewards point earners, and new cardholders can earn a nice sign-up bonus, which can help get you closer to booking flights for your next travel destination. This card also earns 3,000 anniversary points each year and 2 EarlyBird check-ins annually.

Above all, for a modest $69 annual fee, the Rapid Rewards Plus credit card helps you rack up points as cheaply as possible.

Pros

• 2x points on Southwest purchases, local transit and commuting, select streaming and more
• Annual fee that's palatable
• All points earned count towards Companion Pass®

Cons

• In exchange for a lower annual fee, the card's ongoing benefits may seem lackluster
• 3% foreign transaction fee

Southwest offers multiple credit cards with varying annual fees and perks to fit your unique needs. As a small business owner, my favorite Southwest card is the Southwest® Rapid Rewards® Performance Business Credit Card, which includes annual credits for free Wi-Fi on board as well as four free priority boarding credits each year. 

Since I often fly other airlines as well, I prefer putting the bulk of my daily expenses on credit cards that offer rewards that are transferable to multiple airlines and hotels. Sometimes when I run out of Rapid Rewards points, I’ll top off my Southwest account with points from one of these cards in order to book the flight I want. 

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A Roundup of Current Southwest Credit Card Deals

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Some of my favorite cards for travel are the Chase Sapphire Preferred® and the Chase Sapphire Reserve®, and Capital One Venture Rewards Credit Card. All of these cards earn multiple points per dollar spent on travel, and some even include generous travel benefits including insurance for delayed or lost baggage, and trip interruptions such as missed flights. 

3. Earn Bonus Points on Everyday Expenses

Believe it or not, you can earn free flights even without flying or holding a credit card that earns rewards.

Shopping portals are one of the best-kept secrets for earning cash back or points and miles, where businesses pay affiliate partners commission in exchange for driving consumers to their retail websites. In turn, those business partners attract shoppers by sharing a small percentage of the order total.

For example, if I spend $100 sending my mother flowers through a Teleflora shopping portal merchant, I can earn as much as 15% cash back or up to 30 points per dollar. In fact, back when I was a new graduate with a whopping $28,000 annual salary, I earned enough points every year through various airline shopping portals to take a free international Asia trip to see family.

Southwest has a shopping portal, and Slickdeals has its own browser plugin that automatically applies the best coupon deals and discount codes to your order at checkout. But they’re not the only ones: There are dozens of companies that offer rewards ranging from cash back to travel miles to hotel points. Cashbackmonitor.com is a great tool that shows the best rewards you can earn from thousands of retailers.

Earning amounts vary, but some merchants offer reward multipliers ranging as high as 15 or 30 points per dollar. And even small amounts add up relatively quickly: with the right discipline, you’ll be flying high for free in no time, especially on airlines like Southwest that offer award flights from as low as 1,300 points one way. 

So the next time you shop online for new clothes, household goods, or your latest Slickdeals find, take an extra five seconds to see what rewards you can earn by using a shopping portal. 

4. Dine Out (Yes, Seriously)

You can even earn travel points when dining out. In addition to any points you might earn from a dining-friendly credit card, you can sign up for dining programs from Southwest and other airlines that reward you for every dollar you spend at their partner restaurants. You’ll often earn between 1 to 2 points per dollar if you opt-in to receive marketing emails, and will also be eligible to earn bonus points for leaving reviews or participating in special promotions as they arise. 

5. Fly a Buddy For Free With the Southwest Companion Pass 

The Southwest Companion Pass is arguably the most valuable perk in the travel industry, especially if you know how to use it effectively. I’ve been an on-and-off Companion Pass holder since 2013, and have used mine to book more than 120 free flights for relationship partners, family members, and friends. 

The coveted Companion Pass allows you to fly a designated travel companion for free on any flight you book - even if you booked on points. But the pass isn't easy to get: Earning a Companion Pass requires earning 135,000 Rapid Rewards points within a calendar year.

Of course, it can be a challenge to earn 135,000 points in a single year by flying. And unfortunately, Rapid Reward points from dining, shopping, and credit card transfer partners do not count toward your 135,000 quota. So your primary options will be to earn your points by flying paid Southwest flights, or by spending on a Southwest credit card.

Every so often, Southwest has been known to offer promotions for customers interested in earning the Companion Pass on a trial basis - including as recently as September 2022. The rules for earning the promotional pass will vary with each promotion, but the perks are usually well worth the effort required.