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20 Months of Free Flights Guaranteed or Chance of 2 Years of Free Flights

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Update: The credit card offer in this post is no longer available. This offer has ended. The new offer is 40,000 points. Check our credit card page for the latest offers.

Which would you choose: 20 Months of Free Flights Guaranteed or Chance of 2 Years of Free Flights? Your mission should you choose to accept it.

Do you go for the sure thing? Or take a gamble on the hope of something better? Game shows like Let’s Make a Deal count on you risking it all and going for the bigger payoff. Risking a blender is one thing but should you risk months of relaxation?

Is it worth giving up free flights for almost two years for the possibility of four extra months of free flight? Let’s take a look and find out.

But this offer is only valid through June 10, 2019.

20 Months of Free Flights Guaranteed or Chance of 2 Years of Free Flights

You could fly free to places like California

 
Southwest offers a Companion Pass that gives you two years of free flights when you fly 100 flights or earn 125,000 points. They sweetened the offer earlier this year by giving away the Companion Pass after you got and spent $4,000 on one of their credit cards.
 
Throughout the year they offer a higher signup bonus on their credit cards which makes it easier to earn the Southwest Companion Pass. This is one of those times.
 

All four Southwest credit cards were offering a 60,000 point signup bonus when you apply by June 10, 2019. The current offer is 40,000 points.

Southwest Premier Card 40K Points

 

Signup Bonus: 40,000 Southwest points. You can earn 40,000 points after spending $1,000 on purchases within the first 3 months of account opening. 

With the Southwest Rapid Rewards Premier Card you get:

  • Free checked bags (2 per person)
  • 6,000 points each year on your card anniversary
  • 2X points on Southwest purchases, Rapid Rewards hotel and car rental partner purchases
  • 1X point on everything else
  • Earn up to 15,000 tier qualifying points each year
  • No foreign transaction fees
  • $99 annual fee

Why you should get this card: you want to be among the first to board the plane. Using this card earns tier qualifying points towards A-List and A-List preferred status. A-List status gets “A” boarding passes instead of a “B” or “C.”

LEARN MORE HERE

Southwest Priority 40K Points

 

Signup Bonus: 40,000 Southwest points. Earn 40,000 points after spending $1,000 on purchases within the first 3 months of opening your account. 

Perks of the Southwest Rapid Rewards Priority Card include:

  • $75 Southwest travel credit each year
  • Free checked bags (2 per person)
  • 4 upgraded boarding each year
  • 7,500 points each year on your card anniversary
  • 2X points on Southwest purchases, Rapid Rewards hotel and car rental partner purchases
  • 1X point on everything else
  • 1,500 tier qualifying points towards A-List and A-List Preferred status for every $10,000 spend (up to $100,000)
  • 20% back on in-flight purchases
  • No foreign transaction fees
  • $149 annual fee

Why you should get this card: you fly Southwest but not enough to earn A-List status. The four upgraded boarding passes and $75 travel credit make this card worth it for regular Southwest flyers.

LEARN MORE HERE

Southwest Plus Card 40K Points

 

Signup Bonus: 40,000 points. You’ll earn 40,000 points after spending $1,000 on purchases within the first 3 months of account opening.

The Southwest Rapid Rewards Plus Card offers:

  • Free checked bags (2 per person)
  • 2X points on Southwest purchases, Rapid Rewards hotel and car rental partner purchases
  • 1X point on all other purchases
  • 3,000 points each year on your card anniversary
  • No foreign transaction fees
  • $69 annual fee

Why you should get this card: you want another way to earn more Southwest points, don’t mind getting a “B” or “C” boarding pass, and want to pay a lower annual fee.

LEARN MORE HERE

Southwest Premier Business Card 60K Points

Signup Bonus: 60,000 points after spending $3,000 on purchases in the first 3 months of getting your card

With the Southwest Rapid Rewards Premier Business Card you get:

  • Free checked bags (2 per person)
  • 2X points on Southwest purchases, Rapid Rewards hotel and car rental partner purchases
  • 1X point on all other purchases
  • 6,000 points each year on your card anniversary
  • No foreign transaction fees
  • $99 annual fee

Why you should get this card: you want to earn more Southwest points from your business expenses.

LEARN MORE HERE

Southwest Companion Pass

With the Southwest Companion Pass, your companion flies for free with you to 101 US cities (including Hawaii) and 10 countries. The pass is valid for the year it’s earned and all of the following year. 

If you earned it now you’d have 20 months of free flights.

You can use your pass as often or as little as you like. You could fly every day, every weekend, or once every few months. It’s your choice.

Booking flights using your Southwest Companion Pass is easy. When you book your ticket, you can pay cash or use points (so you can travel for free too). Then you add your companion and pay the airline tax of $5.60. 

And with Southwest, if you find a lower price on your flight, you can rebook and change your flight without any penalties. Plus they give you credit for the difference!

To earn that pass you have to fly 100 flights or earn 125,000 points in a calendar year. 

Pro-tip: Chase Ultimate Rewards points transferred from cards like the Chase Sapphire Preferred or the Ink Business Preferred doesn’t count towards the Pass. 

Because the signup bonus on the credit cards counts towards earning the Companion Pass, with a 40,000 point bonus on all four cards: Southwest Priority Card, Southwest Premier Card, Southwest Plus Card, and Southwest Premier Business Card you can almost earn the Southwest Companion Pass from two cards.

Pro-tip: Apply for a personal and business card for a total of 100,000 points.

Normally, you can’t apply for two personal cards. But recently some people have been able to get two personal cards. YMMV (your miles may vary).

Get the Pass Now or Wait

Southwest frequently offers signup bonuses of 50,000 or 60,000 points on all four credit cards towards the end of the year.

This year they’ve offered several opportunities to earn the Southwest Companion Pass and high signup bonuses. But there’s no guarantee that they’ll offer the same bonus later in the year.

Normally, the signup bonus is 40,000 points. You could earn a Companion Pass now and travel for free for the next 20 months. 

Or you can take your chance and hope the cards offer a high signup bonus at the end of the year and with the right timing, get two years of free flights.

But are you willing to wait eight months and risk 4 months of free flights?

I’d rather travel now than wait and possibly lose out on the high signup bonus. But you should do what’s right for you. Are you a gambler? Or are you willing to go for the sure thing?

What You Need to Know

Eligibility

You can apply for these cards if you:

  • Don’t currently have any Southwest credit card
  • Haven’t received a bonus on a Southwest credit card within the last 24 months

Chase 5/24

The Southwest cards are subject to Chase’s 5/24 rule.

This means it could be hard to get approved if you’ve opened 5 new credit cards in the last 24 months aka 5/24.

Conclusion

You can get 20 months of free flights or wait eight months and hope to get two years of free flights. 

Three cards: Southwest Priority Card, Southwest Premier Card, and Southwest Plus Card are offering 60,000 points through June 10, 2019. This offer has ended. The offer is now 40,000 points. But the Southwest Premier Business Card is still offering 60,000 points.

This means you can earn the Southwest Companion Pass if you are approved for two cards: one personal and one business.

Remember Ultimate Rewards points transferred from cards like the Chase Sapphire Preferred or the Ink Business Preferred doesn’t count towards earning the Companion Pass.

Where are you going to fly on Southwest?

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Featured photo courtesy: Austin Neill via Unsplash

Traveling Well For Less has partnered with CardRatings for our coverage of credit card products. Traveling Well For Less and CardRatings may receive a commission from card issuers.


Southwest Rapid Rewards Priority Card

TSouthwest Rapid Rewards Priority Card's newest signup bonus can get you up to 2 years of free flights! The welcome offer is 100,000 points: 50,000 points after spending $2,000 in the first three months; another 50,000 points after spending a total of $12,000 in the first 12 months.
 
My favorite perks about this card are earning 3X points on Southwest purchases, 2X points on internet, cable, phone, streaming, ride share, and Rapid Rewards hotel and car rental partners, $75 yearly travel credit, 4 upgraded boardings each year, and no foreign transaction fees.
 


Chase Sapphire Preferred

The Chase Sapphire Preferred is the best card for beginning travel hackers. It is the first card you should get to start traveling for free because the welcome offer is 60,000 points after spending $4,000 in the first three months.
 
My favorite perks about this card are earning 5X points on travel when booked through the Chase portal (2X if direct purchase), 3X points on dining , $50 yearly credit on hotels booked through the Chase portal, no foreign transaction fees, and transferring points to 13 airline and hotel partners like Hyatt, United, and Southwest.
 


Chase Freedom Unlimited

The Chase Freedom Unlimited is one of my favorite cards for earning cash back card and travel rewards. It offers a welcome offer of $200 after spending $500 in the first three months.
 
My favorite perks about this card are earning 5% cash back at grocery stores the first 12 months (up to $12k), unlimited 1.5% cash back on all purchases and no annual fee. When paired with cards like the Chase Sapphire Reserve, you can use your points to travel for free.
 
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Suruchi

Wednesday 8th of May 2019

Now these cards sounds like a complete bonus with lots and lots of rewards. We would have definitely checked these out but unfortunately we are from India and can’t apply for them.

Debra Schroeder

Monday 13th of May 2019

Hi Suruchi,

They are a great deal. That's unfortunate that India doesn't offer something comparible.

Nicole LaBarge

Tuesday 7th of May 2019

Travel Hacking is so worth it! These Southwest credit cards each have their own benefit. Such good offers and we all want to have a free checked bag!

Debra Schroeder

Monday 13th of May 2019

Hi Nicole,

Travel hacking sure is, it makes more travel possible. :)

Cat Lin

Tuesday 7th of May 2019

Those offers sound great! The free checked bags and no foreign transaction fees are big pluses for us. Too bad we are in Canada and can't apply for them!

Debra Schroeder

Monday 13th of May 2019

Hi Cat,

What a bummer. :(

Rosemary

Tuesday 7th of May 2019

Now that Southwest is starting to fly to more international destinations, their offers sound a lot more interesting. When I was working in my corporate job, I used to fly Southwest all the time and had racked up enough points for the Companion Pass. It's a sweet deal for sure. Will keep this card in mind as Southwest continues to expand :)

Debra Schroeder

Monday 13th of May 2019

Hi Rosemary,

Please do. :)

Jenn and Ed Coleman

Monday 6th of May 2019

That companion pass is a sweet deal. I have several people in the office who travelled enough on business to get a companion pass. Now, their wives get to enjoy per diem with them. Plus, they finally get so see each other since they were travelling all the time.

Debra Schroeder

Monday 13th of May 2019

Hi Jenn and Ed,

Exactly. It's a great perk for business travelers. Plus regular people who like to travel can benefit too. :)

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