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Southwest just extended its reservation schedule, which means you can now book flights through Nov. 2, 2019, including Columbus Day weekend. Up until this point, reservations were only available through Oct. 1, including for its new Hawaii routes. October falls during Hawaii’s shoulder season, when you can still experience great weather while also snagging lower than usual hotel pricing.

It makes sense to book as soon as the Southwest schedule gets extended, especially if you are looking to travel during peak travel dates (i.e., Columbus Day weekend). Southwest has an extremely flexible change and cancellation policy so if you book now and find a lower price at a future date, you can “rebook” your flight at the lower price. Here are the rules for the latter scenario:

  • If You Paid for the Flight: You will receive a Travel Fund credit for the difference in the fare price. You have one year from the date you initially booked the flight to use the credit. Travel Fund credits are nontransferable and can only be used for the same passenger.
  • If You Used Points for the Flight: The difference in points will automatically go back into the account from which those points were originally deducted if you reprice the flight.

Southwest is a low-risk airline to book with from a pricing perspective because if your family’s travel plans change, you can cancel your flight with no cost and if the price decreases, you’ll receive the difference back one way or another.

Book Hawaii for Just $159 One-Way

Now, let’s get to the real important stuff — Hawaii. Just recently, Southwest made its grand announcement that it will start flying to Hawaii on March 17, although some of the routes will not start until as late as the end of May:

  • Oakland (OAK) to Honolulu (HNL): Launches March 17
  • Oakland (OAK) to Maui (OGG): Launches April 7
  • San Jose (SJC) to Honolulu (HNL): Launches May 5
  • San Jose (SJC) to Maui (OGG): Launches May 26
  • Inter-island Honolulu (HNL) to Maui (OGG): Launches April 28
  • Inter-island Honolulu (HNL) to Kona (KOA): Launches May 12

Right now, with the fare schedule being extended, you can book flights to Hawaii for as low as $159 or 10,527 points during the month of October. During the introductory fare sale that we saw last week, the low fare flight prices sold out incredibly quickly. While these prices aren’t as low as they were when Hawaii flights were launched, if you have been eyeing a trip to Hawaii in October, book now. If you are booking a revenue fare, you have 24 hours to cancel for a full refund and if you are booking with points you can pretty much cancel at any point (up to 10 minutes before the flights departure time). With that being said, many other airlines have lowered their fares to Hawaii, so you might see some competitive pricing with another airlines as well.

However, no new Hawaiian routes were introduced with this schedule extension. Note that Southwest’s current Hawaii routes are on 737-800 aircraft and not the 737 MAX, that is currently grounded, but has been tapped for operating future Southwest flights to Hawaii.

Best of all, the Southwest Companion Pass works on all Southwest routes, including Hawaii. Your only requirement is paying the incredibly low taxes of $11.20 round-trip for your companion’s “free” ticket. Even if you are not yet a pass holder, you are allowed to add a companion on later as long as you earn the pass by the time of your flight. (Of course, there must be at least one seat left for sale when you do this.)

Tip: If you have Southwest points and think you will earn a pass by flight time, book your companion a seat on the flight now. Once you earn the pass, you can cancel that person’s existing reservation and add him or her onto your reservation to get that nearly-free flight.

Low Hotel Prices in October

Since October is considered an off-peak time for Hawaii, lodging should be relatively reasonable, too. While all of the Hawaiian Islands are filled with a ton of chain hotels, boutique properties and Airbnb options, here is a small sampling of where you can stay:

Andaz Maui at Wailea Resort

The Andaz Maui at Wailea Resort is a desirable hotel among couples (and some families), but availability is typically extremely limited when using points. Right now, the hotel costs just 25,000 World of Hyatt points a night (jumping up to 30,000 points on March 18,). This is a hotel that plays games with point availability from time to time, but if you look at booking exactly a three-night reservation or a six-plus-night stay, you’ll find that you can easily book with points. When using points, the $45 nightly resort fee is also waived.

 

This property in a suburban location is absolutely beautiful. Kids will love the pools and the beach, and — best of all — the kids club is complimentary for those who meet the age requirements. Free kids clubs are hard to come by in the United States, so this could save you a ton of money on your vacation. (Here are a few more US hotels that offer free kids clubs.)

Courtyard Waikiki Beach

If you are a AAA member, you can actually book a one-bedroom suite at the Courtyard Waikiki Beach for just $191 a night. This is a good option for families who prefer a bedroom separate from the living room and want some extra space to spread out, plus every room has a balcony. This is not an ultra-luxe resort, but there is a pool and you are right in the heart of Waikiki. To top it off, there are no resort fees.

Waikiki Beach, Honolulu. (Photo by AussieActive on Unsplash
Waikiki Beach, Honolulu. (Photo by AussieActive on Unsplash)

Kona Coast Resort

The Kona Coast Resort is one of Wyndham’s Vacation Club properties where you can book a 1,020 square foot one-bedroom villa for just 15,000 Wyndham Reward points. If you prefer another Wyndham property in Hawaii, you can book any of them right now for the same 15,000 points due to their flat award chart (that will change April 3, so make sure to book before then).

If you are low on Wyndham Reward points, the going rate at this property is as low as $143/night during the month of October; if you prefer a two-bedroom, you can stay for just $175/night, which is quite amazing for a room that is over 1,600 square feet! Use your Citi Prestige Card fourth night free benefit and you’ll pay less than $500 for a four-night stay. Despite the affordable price, each room comes with a fully equipped kitchen, which I find extremely appealing when traveling with kids. 

Bottom Line

Now is the perfect time to book a Southwest flight for October, especially if you want to visit Hawaii. If you are low on points, you can always earn more with one of the Southwest co-branded credit cards. Or transfer points from your Chase Ultimate Rewards account if you have the Chase Sapphire Preferred Card or Chase Sapphire Reserve credit cards; points transfer to Southwest at a 1:1 ratio.

My family books all upcoming Southwest flights on the day the schedule is announced to lock in low prices; if the fare decreases at all, I change my flight and receive the difference back in points. Planning now for the future could absolutely save you a boatload of points (or money) on Southwest. For those looking to book holiday travel, the next Southwest schedule extension is planned for May 23, 2019, when they extend through January 5, 2020.

To help you on your Hawaii planning journey:

Jennifer Yellin covers family travel deals for TPG and blogs at Deals We Like. Follow her family’s adventures on Twitter and Instagram.

Featured image by John M Lund Photography Inc / Getty Images

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