Southwest Schedule Extended Through Nov. 2, Plus $159 Fares to Hawaii

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About 30 minutes ago, Southwest extended their flight schedule which means you can now book a Southwest flight through November 2, 2019. Up until now, you could only book flights through October 1st, so you can now go ahead and book flights for all of October. This is great for those trying to plan a long weekend getaway over Columbus Day Weekend. For many peak dates, today might actually be the best day to book to grab “low” fares.

Book Now, Cancel Later

I personally love the flexibility of Southwest because I can cancel my vacation plans with NO PENALTY! I can also continue to watch the prices of the flight and IF they go down in price I can get the difference in points back! You can read more about the exact process and steps to go about this with these blog posts: “Changing and Canceling a Southwest Flight”, “If a Southwest Flight Goes Down in Price….”, and “Seeing if a Southwest Flight Went Down in Price is Now a Lot Easier“. But essentially if you…

  • Paid for the flight… You will receive a voucher for the difference in fare price to be used one year from the date the flight was originally purchased (NOT the date the change process took place). This voucher is non-transferable. The voucher will be tied to the confirmation number of the original flight. There is NO fee for this.
  • Booked your flight using points… The difference in points will go back into your account immediately. Although, you might want to cancel and rebook. Again, there is NO fee for this. This is why I love booking Southwest flights using points!

Book Now, Add Your Companion Later

If you are going for the Southwest Companion Pass, where you can fly a companion 2-for-1, you can still book your flight now and add your companion later! Even if you are not officially a companion pass holder just yet, but know you will be within a month or two, you can still book the first passengers flight now. Once you actually receive the pass, you can go ahead and add on your companion to your reservation—for free, plus taxes/fees!

As long as there is one seat for sale, you can book your Companion!

Fly to Hawaii for 10,527 Points or $159 One-Way

Southwest’s new Hawaii service is about to start in just a few days on March 17th! When those flights were originally announced, we saw incredibly low fares of just $49 one-way! Unfortunately, this schedule extension did not bring the same fares, although you can still book for $159 one-way during the month of October. While you might find similar pricing on other airlines (maybe?), remember you can fly 2-for-1 with the Southwest Companion Pass! Also, no additional Hawaiian routes were announced, so you are still looking at the following routes:

  • Oakland (OAK) to Honolulu (HNL)
  • Oakland (OAK) to Maui (OGG)
  • San Jose (SJC) to Honolulu (HNL)
  • San Jose (SJC) to Maui (OGG)
  • Inter-island Honolulu (HNL) to Maui (OGG)
  • Inter-island Honolulu (HNL) to Kona (KOA)

Hopefully we will see additional routes announced in the near future, or at least with the next schedule extension.


Some of the schedule is still a little funky. There are some routes where most flights during the day were sold out, which seems incredibly odd. Clearly, for a random date in October, this is absolutely not the case. This makes me believe that the schedule is not fully loaded or that some of those flights were originally supposed to fly 737 MAX planes and until they figure out what they are doing with those itineraries, they are not selling seats to passengers (yet).

If there is a certain route are looking to book and it says Sold out across the board, I would keep on checking the Southwest site to see if availability opens up. I will definitely be paying attention to this as well and will report more when I have some more information to share.

For now though, if there is a flight you are looking to book through Nov. 2, you might want to consider booking now!

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