Southwest adds new cities (and you can fly for free)

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In the midst of a pandemic, Southwest has expanded and continues to expand its network. To name a few, Steamboat Springs, Sarasota (Ryan’s hometown!), Telluride, and Palm Springs were recently added.

Taylor and her seashell in Sarasota, home to Siesta Key, which is consistently voted one of the best US beaches by various publications and entities

Last week, Southwest announced that service to Bozeman, Montana, and Destin, Florida will begin in May. Destin, Florida excites us because it’s another way to get to one of our favorite beach areas, 30a (with the other airport being Panama City Beach). Service to Bozeman, Montana will be of interest for anyone looking to visit Yellowstone or Big Sky.

These routes are already available for purchase (paid or on points) at Southwest.com. There is a sale on these routes until March 4, 2021. Southwest has an extremely generous cancellation policy so it’s worth booking now if you have a trip in mind.

Southwest to fly to destin 2021
Service to Destin/Ft. Walton Beach (VPS) begins May 6, 2021

Connecting flights are available from 50 cities. There will be at least one nonstop daily flight each way from these 4 cities:

  • Baltimore/Washington (BWI)
  • Chicago Midway (MDW) beginning June 6
  • Dallas Love Field (DAL)
  • Nashvile (BNA)

One way fares start at $69 which is usually around 4,000 Rapid Rewards points if you want to book with points.

Service to Bozeman, Montana (BZN) begins May 27, 2021

Connecting flights are available from 50 cities. There will be at least 2 nonstop daily flights each way from 2 cities:

  • Denver (DEN)
  • Las Vegas (LAS)

One way fares start at $39 which is usually less than 2,000 Rapid Rewards points if you want to book with points.

How to book free flights on Southwest

Southwest Rapid Rewards points are the currency of Southwest’s loyalty program. Obviously you earn them by flying, but the other way to accumulate lots of points is through credit card spending and sign up bonuses.

Chase issues 5 Southwest Rapid Rewards credit cards.  All of these cards earn Southwest Rapid Rewards points which you can redeem for free Southwest flights. 3 are personal cards and 2 are business cards.

A Southwest Rapid Rewards credit card is not the only way to earn Southwest points from credit cards

Our favorite cards are those that earn points with multiple redemption options. Chase Ultimate Rewards is one of our favorite rewards programs because there are 10 airline transfer partners and 3 hotel partners. Also, there are even more options when you redeem Chase Ultimate Rewards points in the redemption portal. You can read all about the Chase Ultimate Rewards system here.

Chase Ultimate Rewards has 10 airline transfer partners.  Southwest is one of the Chase Ultimate Rewards transfer partners. This means that you can transfer your Chase Ultimate Rewards to your Southwest Rapid Rewards account at a 1:1 ratio. Then you can use the Southwest Rapid Rewards points to book flights just like you would if you were earning Southwest Rapid Rewards points from Southwest credit cards.

Chase Ultimate Rewards airline partners 2021

The obvious choice for amassing Southwest Rapid Rewards points would be Southwest co-branded credit cards from Chase. But other than those trying to earn a Southwest Companion Pass, most people would benefit more by opening a transferable Chase Ultimate Rewards earning card.

The current welcome offer on the Chase Sapphire Preferred card is 100,000 Ultimate Rewards points. The Chase Sapphire Preferred credit card also earns 2 points per dollar on Southwest flights.  But you get 2 points per dollar on all travel, not just Southwest flights. Also, earn 2 points per dollar at restaurants.

Remember, those points transfer to Southwest or 9 other airlines. If you redeem 100k Ultimate Rewards points earned from your Chase Sapphire Preferred in the Chase redemption portal, those points would be worth $1250 in travel. With transfer partners, 100,000 points could be worth even more than $1250.

Earn your first 100,000 Ultimate Rewards points today!  Click here for 25 valuable ways to redeem the bonus.

Chase Sapphire Preferred 2021

I almost always encourage people to open a Chase Ultimate Rewards earning card before opening co-branded cards such as the Southwest cards from Chase. You can read more details about why in this post: 4 reasons to open a Chase Sapphire Preferred instead of a Southwest card. The exception is when your goal is to earn a Southwest Companion Pass.

Southwest Rapid Rewards personal credit cards

The current offer on all 3 versions of Southwest personal cards is 40,000 Rapid Rewards points after spending $1,000 in the first 3 months. Also, new cardmembers will earn 3 points on dining, including eligible takeout and delivery services for the first year.

Here are other details about each of the cards:

Southwest Rapid Rewards Plus Credit Card

The annual Fee is $69. Bonus Categories include 2 points per dollar on Southwest airfare and Rapid Rewards hotel and car rental partner purchases, and you’ll earn 1 point per dollar on all other purchases. Extra Benefits inclue 3,000 bonus points every anniversary.

Southwest Rapid Rewards Premier Credit Card

The annual Fee is $99. Bonus Categories include 2 points per dollar on Southwest airfare and Rapid Rewards hotel and car rental partner purchases, then you’ll earn 1 point per dollar on all other purchases. Extra Benefits include 6,000 bonus points every anniversary, the ability to earn tier qualifying points towards A-List status, and no foreign transaction fees.

Southwest Rapid Rewards Priority Credit Card

The annual Fee is $149. Bonus Categories include 2 points per dollar on Southwest airfare and Rapid Rewards hotel and car rental partner purchases, and you’ll earn 1 point per dollar on all other purchases. Extra Benefits include 7,500 bonus points every anniversary, $75 annual Southwest credit, 4 upgraded boarding positions per year, 20% back on inflight drinks and WiFi. Also, earn tier qualifying points towards A-List status, and no foreign transaction fees.

Southwest Rapid Rewards credit cards 2021

While we love Southwest and their loyalty program, you can only book Southwest flights with Southwest Rapid Rewards points

All 5 Southwest credit cards earn Southwest Rapid Rewards points.  Southwest Rapid Rewards points cannot be transferred to hotel programs (such as World of Hyatt), bank programs (such as Chase Ultimate Rewards), or other airlines.  Southwest is not part of an airline alliance and they do not have partner airlines. This means that you can only book Southwest flights with Southwest Rapid Rewards points. On the other hand, earning transferable points such as Chase Ultimate Rewards will give you more redemption options.

That said, Chase Ultimate Rewards points will not qualify for the Companion Pass if you transfer them to Southwest. So your decision between a Chase Sapphire Preferred or other UR earning card and a Southwest card should be pretty simple. It really just comes down to whether or not having the Companion Pass is your top priority.

A few reasons we love Southwest Rapid Rewards

Southwest is a great airline for many reasons: low fares, free checked bags, friendly employees, free changes/cancellations, and an easy-to-use loyalty program.

If you live in a city that Southwest serves, Southwest Rapid Rewards is a great loyalty program.

  • Points are easy to earn and use
  • Unlike most airline loyalty programs, award ticket availability isn’t limited
  • Low fares=low redemption costs
  • You can make your points twice as valuable if you are able to earn a Southwest Companion Pass
The Southwest Rapid Rewards program does not have an award chart

Redemption pricing for Southwest award flights is directly tied to the paid fare at the time of booking.  In other words, a lower fare will require a lower amount of Southwest Rapid Rewards points.  On the other hand, a higher fare is going to cost more points.  

Unlike most other airline programs, if a seat is available to book with money, you can book it on points. But this isn’t always a good thing. If fares are higher, more points are required. The examples below are only great because the paid fares were low. Having the Companion Pass would still potentially make for a good deal, but more points are going to be required during peak travel times when paid fares are higher.

With Southwest, you do not have to worry about award ticket availability

Southwest does not limit the amount of tickets available to book on points like American Airlines and most other airline programs.  You will always be able to book an available seat with Southwest Rapid Rewards points, but it might not be the lowest redemption option if you’re redeeming Chase Ultimate Rewards points. You can transfer Chase Ultimate Rewards points to Southwest, but if fares are higher, a different Chase Ultimate Rewards airline partner may have better redemption pricing.

Southwest Rapid Rewards credit cards 2021

Southwest Rapid Rewards Points are twice as valuable if you have the Companion Pass

The 40,000 points you earn with the current sign up offer could easily book a roundtrip flight. But if you have a Companion Pass, the value doubles since you would be able to add your Companion to any booking. If you’re able to book with Rapid Rewards points during a fare sale like the one currently going on, you could probably book more than one trip. For example, I found a roundtrip from Dallas to Destin for around 8,000 points. Although it would be a connecting flight, I also found a roundtrip between Dallas and Bozeman for around 12,000 total. I could book both of these and add Ryan to Both. so for a total of 20,000 points, I would be able to book 4 tickets total!

We took the kids to Steamboat for less than 10,000 Rapid Rewards points per ticket thanks to a sale on the recently added route between DAL and Steamboat Springs

You can read a more in-depth post about the Companion Pass here, but here are a few facts:

  • Unlike annual companion passes that are valid for one flight per year (such as the Alaska Airlines companion pass) that come with some credit cards, the Southwest Companion Pass allows you to book a companion as many times as you want for the entire period in which your pass is valid.
  • You can add your companion to any ticket booked on Southwest.  That includes tickets booked on points!
  • This includes tickets to Southwest’s international destinations in Mexico, Central America, and the Caribbean.
  • Generally, you will only pay $5.60 in taxes and fees for your companion each way.  This may be slightly higher if you’re booking an international trip due to departure taxes and other fees imposed by foreign governments.
  • You can only designate one companion at any given time but you can change your companion up to 3 times per year
  • The companion does not have to be a family member, it can be anyone you choose
  • You must be present in order for your companion to fly.  In other words, you cannot book a flight, add a companion, and then cancel your flight but still have the companion fly.
  • If you earn the pass after you’ve already booked a trip, you can go back and add the companion to your reservation
  • There are no blackout dates or seat restrictions

See terms and conditions on southwest.com.

chase sapphire preferred bonus category, chase ultimate rewards, southwest rapid rewards credit cards, chase southwest credit cards, chase ultimate rewards transfer partners
2 for the price of 1!

Common questions

Can I have a Chase Sapphire Preferred and a Southwest Rapid Rewards credit card at the same time?

Yes, and I actually encourage it. If you’re trying to earn the Southwest Companion Pass, you will want to start with Southwest cards. After that, a Chase Ultimate Rewards earning card should be your next move.

Remember, all of these cards are subject to 5/24, so you will want to open them before opening credit cards from other banks!  Once you’ve opened 5 cards, you will not be approved for any Chase 5/24 cards until 25 months after your 5th newest card was opened.

 Can I have 2 Southwest credit cards?

You cannot have more than 1 personal version of a Southwest credit card at the same time.  But you can have one personal card and a business card.

Southwest Rapid Rewards credit cards are subject to Chase 5/24

If you do not know what this is, read this post about Chase’s 5/24 policy. 

Chase has an unofficial policy that is known as the 5/24 rule.  It means that if you have opened 5 or more cards from ANY bank (not just Chase) in the past 24 months, you will not be approved for any Chase 5/24 cards until 25 months after your 5th newest card was opened. All Chase cards discussed on this site are now 5/24 cards, therefore, it is important to open the Chase cards that you want before opening cards issued by other banks.

Final Thoughts

These two new destinations plus the destinations recently added by Southwest are much welcomed in a year full of disappointment for travelers. We hope to visit Montana/Yellowstone soon!

The two best ways to earn free Southwest flights via credit card rewards are the obvious Southwest co-branded cards from Chase and the less obvious choice of transferable Ultimate Rewards earning cards from Chase such as the Chase Sapphire Preferred.

Chase Sapphire Preferred 2021

Advertiser disclosure: The Miles Genie has partnered with CardRatings for our coverage of credit card products.  The Miles Genie and CardRatings may receive a commission from card issuers.

Comments below are not provided or commissioned by the bank advertiser. The comments have not been reviewed, approved or otherwise endorsed by the bank advertiser. It is not the bank advertiser’s responsibility to ensure all posts and/or questions are answered.

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