New at Southwest in 2017: Flights to Hawaii, Better Reservations, & Companion Pass Changes

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Lyn writes about Southwest Airlines on her blog and I’ve asked her to update us on the latest happenings with the airline during this first quarter of 2017.

Lyn:   There have been some exciting changes to Southwest Airlines at the beginning of 2017, especially with improvements to their reservation system and more promised updates coming soon.

New Southwest Airlines Routes 2017

Hawaii Is on Southwest’s To-Do List! You’ll Be Able to Book a Ticket on Their New Reservation System. But Taking a Companion Will Be More Challenging!

I’ll share with you the newest destinations, when Hawaii may become a reality, and changes to how you can earn the Southwest Companion Pass. It’s all the latest Southwest news you need to know!

Changes to How to Earn the Southwest Companion Pass

At the beginning of the year, Southwest updated its Terms & Conditions to say points transferred from hotel and car loyalty programs, as well as e-Rewards, e-Miles, Valued Opinions and Diners Club, no longer qualified for the Southwest Companion Pass.

Daraius and Emily believe the Southwest Companion Pass is the best deal in travel, as it allows 1 person to fly almost free with you for up to 2 years! 

New Southwest Airlines Routes 2017

Transferred Hotel Points No Longer Qualify for the Southwest Companion Pass, But There Are Still Plenty of Other Ways to Earn This Best Deal in Travel

This angered many of us who look forward to earning the Companion Pass every year and include such points as part of our plans.  Because they gave no warning of the change, Southwest granted a grace period through March 31, 2017, to continue to allow these points to qualify for the pass.  That period has now ended.

Here are the ways you can now earn points that qualify for the Southwest Companion Pass:

  • Paid flights on Southwest
  • Points earned through Chase Southwest Rapid Rewards credit cards
  • Base points (not BONUS points) earned via transactions with Southwest Rapid Rewards partners, which may include the Southwest Rapid Rewards Shopping Portal, car rentals, paying your electric bill, Southwest Rapid Rewards Dining, and other programs

Reservation System Updates

Southwest has an outdated reservations system that has limited their ability to schedule different flight times on different days (you may notice it’s the same schedule nearly every day).  This is also the reason you can only book flights about 6 months ahead.  But they are working hard to update it, and we’ve already seen some improvements in the last few months.

New Southwest Airlines Routes 2017

Changes to Southwest’s Reservation System Mean More Flexible Flight Schedules, Longer Booking Windows, and Easier Re-Bookings

For example, when they opened the Southwest flight schedule through November 3, they explained they are now able to optimize the schedule so that Monday through Friday flights are nearly the same each day, while Saturdays and Sundays each have different schedules.

The changes to the reservations system will eventually make re-bookings easier and result in shorter waits for connecting flights.

New Southwest Airlines Routes 2017

While Southwest already flies to Mexico, Jamaica, the Bahamas, the Dominican Republic, Costa Rica, and Cuba, they’ve added yet another warm weather international destination: Grand Cayman.  

Beginning June 4, 2017, you’ll be able to fly to the Cayman Islands on Southwest via Fort Lauderdale.

New Southwest Airlines Routes 2017

Beginning June 4, You Can Book Southwest Flights to the Cayman Islands!

What about other new Southwest Airlines routes for 2017 like Hawaii?  Southwest Airlines CEO Gary Kelly has continually said Southwest has plans to add Hawaii – and Canada – as destinations, but that has yet to happen.

The bloggers at recently said on Million Mile Secrets that flight attendants announced on a recent flight to Aruba that Southwest WILL be going to Hawaii soon!  I think once Southwest gets their reservation system fully upgraded, Hawaii will be more practical.

Southwest officials also said they plan to increase service to Mexico with more flights to Mexico City.

What’s Coming on Southwest

On October 1, 2017, Southwest will add 9 brand new 737-MAX 8 aircraft to its fleet, retiring its 737-300s.

By the end of the year, they will have 14 of the new airplanes in place.  The new planes have the Boeing Sky interior with Southwest’s Heart layout, as well as large pivoting overhead bins and will largely be used for long-haul flights.

New Southwest Airlines Routes 2017

Southwest Will Add 14 New 737-MAX 8 Planes to Its Fleet by Year’s End

Additionally, Southwest has promised that all planes will have Wi-Fi by year’s end.  Until that happens, here’s how to check if your flight will have Southwest WiFi.

Odds & Ends

Flying standby on Southwest just got a little easier this quarter.  Elite status members, who include A-List and A-List Preferred members (achieved by accumulating a certain number of flights and/or Southwest points), can fly standby free, and in February, they removed the 2-hour window restriction.  Now elite members can fly standby anytime on the same day as the original flight.

New Southwest Airlines Routes 2017

Now Southwest Elite Status Members Can Fly Standby FREE Anytime During the Same Day as Their Original Flight

You also now have a new alcoholic beverage option when flying Southwest!  In addition to choosing from various wines, beers, spirits and cocktails, now you can order sparkling wine, perhaps to celebrate a special occasion like a honeymoon, graduation, or anniversary!  Here’s how to get Southwest free drink coupons so you can say cheers in the air without spending a dime!

Finally, when enjoying Southwest’s free entertainment on Wi-Fi enabled planes, you can now opt to watch your favorite sports team on ESPN or ESPN2, and the younger members of your crew can tune into Disney – all new channels you can watch on your own compatible devices.

Bottom Line

Southwest has been busy this quarter, making the flying experience even more enjoyable from improved flight schedules to new planes and destinations.  Now, kick back with a glass of sparkling wine and enjoy your favorite sport on ESPN on your next Southwest flight!

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6 responses to “New at Southwest in 2017: Flights to Hawaii, Better Reservations, & Companion Pass Changes

  1. I had hoped them moving to the new system would make it easier to connect flights that would not connect in the reservation system before and I’ve seen I’ve seen that in some flights I’ve searched but now flights that I have taken, that did connect in the system are no longer connecting and I don’t understand why. It is a pain to have to book separate flights to get to a destination. I’ve also noticed that with the changes of the number of flights and flight time changes, it has knocked out some of the Carribbean destinations from Tulsa, unless I overnight in Houston. I hope they are still working on this aspect of it.

  2. One expected downside of the improved reservation system: WN can now detect and cancel duplicate or near-duplicate bookings. This has been well covered in other blogs, so I won’t go into a lot of detail here. (I have no complaints – they’re still the most flexible domestic airline, and the old reservation system was far too easy to abuse.)

  3. I’ve been waiting with bated breath for WN to add Hawaii as destination and am excited to hear that may finally happen soonish. Sure, I have other ways of getting there, but the companion pass in that case (assuming it’s permitted for use on that route) would be ideal for us. Thinking back on it, it’s been right around 3 years since I made my first & so far only trip there…really need to go back. Anyway, Thanks D.D. & Lyn for this coverage of Southwest developments.

  4. Why or why can’t one do a search for co terminals, eg., NYC to WAS? I sometimes have to do 6 separate searches to see the options?

  5. Maybe I’m just getting hung up on phrasing but are you saying that it will be more difficult to use a companion pass on Hawaii flights or did you just mean it’s harder to get the companion pass in general? Thanks.

    • I second the confusion/complaint. More like “click bait” — it got us to read for something new — that isn’t there. The only companion pass change that I can discern here is very old news, re. the tired complaints about not being able to transfer hotel this or that. (an issue very much overcome by recent promo bonuses for the SWA credit cards — both of them — to 60k…. but NO MENTION OF THAT)

      Alas, this essay wasn’t up to usual MMS editing standards….. I too made the connection at first, that somehow the routes to Hawaii would not be eligible for companion pass…. But then see utterly no evidence, even speculation to that effect.