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

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

Update: The credit card offer in this post is no longer available. The new offer is 85,000 points after spending $3,000 on purchases in the first three months of account opening. Check our credit card page for the latest offers.

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 135,000 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 85,000 points.

Southwest Rapid Rewards® Premier Credit Card 85K Points

Southwest Rapid Rewards® Premier Credit Card Signup Bonus: 85,000 Southwest points. You can earn 85,000 points after spending $3,000 on purchases within the first 3 months of account opening.

With the Southwest Rapid Rewards® Premier Credit Card you get:

• Free checked bags (2 per person)
• 2 EarlyBird Check-In® every year
• 10,000 Companion Pass® qualifying points boost each year
• 6,000 points each year on your card anniversary
• 3X points on Southwest® purchases
• 2X points on Rapid Rewards® hotel and car rental partner purchases, rideshare, local transit and commuting
• 1X point on all other purchases
• Earn up to 15,000 tier qualifying points each year
• No foreign transaction fees
• $99 annual fee
• Member FDIC

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 ABOUT THE Southwest Rapid Rewards® Premier Credit Card

Southwest Rapid Rewards® Priority Credit Card 85K Points

Signup Bonus: 85,000 Southwest points. Earn 85,000 points after spending $3,000 on purchases within the first 3 months of account opening.

Perks of the Southwest Rapid Rewards(R) Priority Credit Card include:

• $75 Southwest travel credit each year
• Free checked bags (2 per person)
• 10,000 Companion Pass® qualifying points boost each year
• 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, rideshare, local transit and commuting
• 1X point on all other purchases
• 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
• Member FDIC

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 ABOUT THE Southwest Rapid Rewards® Priority Credit Card

Southwest Rapid Rewards® Plus Credit Card 85K Points

Southwest Rapid Rewards® Plus Credit Card Signup Bonus: 85,000 points. You’ll earn 85,000 points after spending $3,000 on purchases within the first 3 months of account opening.

The Southwest Rapid Rewards® Plus Credit Card offers:

• Free checked bags (2 per person)
• 2 EarlyBird Check-In® every year
• 10,000 Companion Pass® qualifying points boost each year
• 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
• Member FDIC

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 ABOUT THE Southwest Rapid Rewards® Plus Credit Card

Southwest® Rapid Rewards® Premier Business Credit Card 60K Points

Southwest® Rapid Rewards® Premier Business Credit Card Signup Bonus: 60,000 points after spending $3,000 on purchases in the first 3 months after opening your account.

With the Southwest® Rapid Rewards® Premier Business Credit Card, you get:

• Free checked bags (2 per person)
• 3X points on Southwest® purchases
• 2X points on 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
• Member FDIC

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

LEARN MORE ABOUT THE Southwest® Rapid Rewards® Premier Business Credit Card

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 135,000 points in a calendar year.

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

Because the signup bonus on the credit cards counts towards earning the Companion Pass, with a 50,000 point bonus on all three personal cards and Southwest Premier Business Card you can earn the Southwest Companion Pass from two cards.

Pro-tip: Apply for a personal and business card for a total of 189,000 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 can 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 when you combine the signup bonus on one of the personal Southwest cards and the bonus on a Southwest business card.

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® Card don’t count towards earning the Companion Pass.

Where are you going to fly on Southwest?

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Southwest® Rapid Rewards® Premier Business Credit Card

The Southwest® Rapid Rewards® Premier Business Credit Card is currently offering a quick way to get up to two years of free flights. The welcome offer is up to 120,000 points: 60,000 points after spending $3,000 in the first three months. And another 60,000 points after spending a total of $15,000 in the first 9 months. This offer will end soon.

 

My favorite perks about this card are earning 3X points per $1 on Southwest purchases, 2X points on rideshare, 2 free Earlybird checkins, and no foreign transaction fees.

 

Review of the Southwest Premier Business card.

 

Learn more about the Southwest® Rapid Rewards® Premier Business Credit Card and how to apply

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Capital One Venture X Business

With the Capital One Venture X Business the welcome offer is 150,000 mile bonus after spending $$30,000 on purchases in the first three months.

 

My favorite perks about this card are free Capital One Lounge access, earning 2X points on all purchases, and transferring miles to over 15 travel loyalty programs.

 

Learn more about the Capital One Venture X Business and how to apply

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Chase Sapphire Preferred® Card

The Chase Sapphire Preferred® Card is the best card to get started in the world of miles and points. 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.

 

Learn more about the Chase Sapphire Preferred® Card and how to apply