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I’m a big fan of Southwest Airlines for many reasons. From the family-friendly attitude, the free checked bags 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 10 years.
Here’s how I book more than a dozen free flights each year on Southwest.
🚀 New Boosted Southwest Welcome Bonus
Right now, Southwest consumer credit card holders can earn a whopping 75,000 bonus points after spending $3,000 on purchases in the first 3 months from account opening. This bonus is notably larger than what’s typically available, making now an ideal time apply.
1. Sign Up for a Southwest Frequent Flyer Account
I’ve been a Southwest Rapid Rewards loyalty program member for the past 15 years. I’ve been able to earn points on every 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 booked book hundreds of free flights over the years. Even if you only fly once or twice a year, those points add up, and since Southwest points never expire, you can keep saving them until the right time.
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 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. Get 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
Secure application on issuer’s website
- Our Rating 4.0/5 How our ratings work
- APR21.49% - 28.49% (Variable)
- Annual Fee$69
Sign Up Bonus
75,000Southwest Rapid Rewards Points
Earn 75,000 bonus points after spending $3,000 on purchases in the first 3 months Dollar Equivalent: $1,125 (75,000 Southwest Rapid Rewards Points * 0.015 base)
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.
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.
- 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®
- 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 to book the flight I want.
A Roundup of Current Southwest Credit Card Deals
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 websites. In turn, those business partners attract shoppers by sharing a small percentage of the order total.
I once spent $100 sending my mother flowers through a Teleflora shopping portal merchant and earned 15% cash back. And when I was a new graduate with a $28,000 salary, I earned enough points 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: Dozens of companies 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, especially on airlines like Southwest that offer award flights from as low as 1,300 points one way.
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 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 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.
Unfortunately, Rapid Reward points from dining, shopping, and credit card transfer partners don't count toward your quota. So your primary options are to earn points by flying paid Southwest flights, or by spending on a Southwest credit card.