How You and Your Bestie Can Fly—and Stay—in Hawaii for $22!

A Motel 6 hotel in Columbus, Ohio will cost ~$60 per night. My bestie a/k/a my wife, and I, recently stayed in Maui, Hawaii, for a week. How much did I have to pay for roundtrip airfare and seven days at an oceanfront resort? $22.40!


Say what?


That's right! Thanks to the wonderful world of credit card miles & points. In this post, I'll show how it was done, which will give you a blueprint of how to do it!


Award Travel can save thousands of dollars on travel expenses—such as to Maui, Hawaii!
Award Travel can help you save thousands of dollars on travel expenses—such as to Maui, Hawaii!

All opinions and reviews expressed herein are the author's alone and have not been reviewed or approved by any credit card issuer, airline, bank, hotel chain, or other entity. Some of the credit card offers and links appearing in this article are from companies from which we may receive commission or a referral bonus when you click on the link. You do not need to use our links but we appreciate it when you do—it helps support our website! Some of the credit card offers mentioned herein are time-sensitive and may no longer be available.


How to Book Your Award Flight


Although this is not a hard and fast rule, I generally recommend that you book your Award Flight first—before booking your hotel. Award availability can dry up, and you don't want to book your hotel only to find out that the price for your Award Flight has doubled, or even tripled!


I used Rapid Rewards®—the loyalty program of Southwest Airlines—to book our Award Flights. I have the Companion Pass which allows you to designate a companion to fly with you on any Southwest Airlines flight for free; your traveling companion only needs to pay the taxes for the ticket.


I designated my bestie—my wife—and we originally only needed 40,872 points + $22.40 to book roundtrip tickets from Columbus, Ohio (CMH) to Maui, Hawaii (OGG). However, the next day, Southwest ran a 30% promotion, and I was able to get 12,260 points redeposited into my Rapid Rewards® account after talking to a Southwest Airlines representative!


Cha-ching!


In other words, we both redeemed roundtrip Award Flights from CMH to OGG for a total of 28,612 points + $22.40!


Award Flight: Primary roundtrip itinerary from CMH to OGG for 40,872 points + $11.20!
Award Flight: Primary roundtrip itinerary from CMH to OGG for 40,872 points + $11.20! Image courtesy of Southwest Airlines
Award Flight: Companion roundtrip itinerary from CMH to OGG for 0 points + $11.20!
Award Flight: Companion roundtrip itinerary from CMH to OGG for 0 points + $11.20! Image courtesy of Southwest Airlines
Southwest's 30% promotion resulted in both roundtrip Award Flights to cost 28,612 points + $22.40!
Southwest's 30% promotion resulted in BOTH roundtrip Award Flights requiring 28,612 points + $22.40! Image courtesy of Southwest Airlines

How much cash would this same itinerary have cost me? It would have been $1,163.


2 Cash Flights: Roundtrip itinerary from CMH to OGG for $1,163
2 Cash Flights: Roundtrip itinerary from CMH to OGG for $1,163. Image courtesy of Southwest Airlines

In other words, I redeemed 28,612 points at a value of ~3.9 cents per point—when factoring in the Companion Pass! I strive to get at least 1.5 cents per point when redeeming my miles/ points.


How to Book Your Award Stay


It is no secret in the Award Travel community that World of Hyatt® is one of the best hotel elite status programs out there. One tip is to utilize their off-peak pricing. That is exactly what we did!


We stayed at Lahaina Shores Beach Resort, a Destination by Hyatt Residence. It is a category 4 hotel; the standard rate for the standard room is 15,000 points per night. The peak rate is 18,000 points per night. However, off-peak is only 12,000 points per night!


We were able to transfer 72,000 Chase Ultimate Rewards® points to my World of Hyatt® account and redeem 6 nights at this resort for 72,000 Hyatt points! How much did we pay in resort fees and taxes? Zero.

Award Stay: 6 nights at Lahaina Shores Beach Resort for 72,000 points!
Award Stay: 6 nights at Lahaina Shores Beach Resort for 72,000 points! Image courtesy of Hyatt

How much cash would this same stay have cost me? It would have been $1,961.81!


Cash Stay: 6 nights at Lahaina Shores Beach Resort for $1,961.81
Cash Stay: 6 nights at Lahaina Shores Beach Resort for $1,961.81. Image courtesy of Hyatt

In other words, I redeemed 72,000 points at a value of ~2.7 cents per point!


Lahaina Shores Beach Resort is a great location to stay in Maui!
Lahaina Shores Beach Resort is a great location to stay in Maui!

The Value of Credit Cards!


My wife and I were able to save over $3,000 on this trip to Maui, Hawaii, using credit card rewards. In other words, if we had only been using a debit card on all our purchases, we would have paid an additional $3,000 for this trip! This is one reason using a credit card has tremendous advantages over using a debit card.


The Feast at Lele—regarded as one of the best Luau's in Maui
The Feast at Lele—regarded as one of the best Luau's in Maui.

If there is one thing I could change about credit cards, it is this: I wish I used them more frequently when I was younger! I wish someone had educated me about the benefits of Award Travel. But, hindsight is 20/20.


"Responsible credit card use can open the door to Award Travel—and save you thousands of dollars on travel expenses every year."

Nevertheless, you can learn from our experiences. I enjoy teaching others how to benefit from Award Travel and would be happy to help you out as well! The purpose of this post is not to brag—it is to open a door to travel to different parts of the world you may not have thought possible. Because my wife has a brain tumor, we have had to find creative ways to reduce our travel expenses—Award Travel was the solution! You can also learn Award Travel tips from our recent vacation in Greece. Learn how to fly—and stay—in Greece for $100!


How to Choose Your Credit Card


Choosing the right credit card is important in your Award Travel journey. You will want to focus on Flexible Points Credit Cards. Nevertheless, co-branded credit cards do have their place in your credit card portfolio.


In my opinion, the best credit card to get started with is the Chase Sapphire Preferred® Card. The current sign-up bonus is 60,000 Ultimate Rewards® points. Southwest Airlines is a transfer partner of Chase. Hence, you can transfer your Ultimate Rewards® points to your Southwest Rapid Rewards® account. You can apply for this card here! You can also learn more about this card in the following post: Chase Sapphire Preferred—The Best Credit Card Just Got Better!


Southwest Airlines also has three personal co-branded Chase credit cards that will help you directly earn Rapid Rewards® points. In my opinion, the best of the three is the Southwest Rapid Rewards® Priority Credit Card. It currently has a 50,000 points sign-up bonus with only a $1,000 minimum spend threshold. You can apply for this card here!


Additional credit cards that will help you increase your stash of Ultimate Rewards® are: Chase Freedom Unlimited® and Chase Freedom Flex℠. Both currently have a sign-up bonus of 20,000 Ultimate Rewards® points. My wife and I have both of these cards. When paired with the Chase Sapphire Preferred® Card or the Chase Sapphire Reserve® they make up the "Chase Trifecta." The "Chase trifecta" is a term known by Chase Ultimate Rewards® enthusiasts. Essentially, it is strategically combining three Chase credit cards to boost their rewards-earning potential. Not all Chase-branded credit cards "qualify" for this special designation. You can apply for both of these cards here! You can learn more about these cards in the following posts: Chase Freedom Unlimited—Don't Miss Out on This Card! Chase Freedom Flex—A Remarkable No Annual Fee Card!


The Bottom Line


Traveling to your dream destination can become a reality—with proper planning. Do you feel overwhelmed with all the options available when it comes to redeeming your miles & points? Would you like some assistance to get you started in the right direction? You will benefit from the services of a Credit Card Miles & Points Consultant. You will be assisted with regards to earning miles & points through credit card use and leveraging those miles & points for Award Travel. Or, feel free to use any of our Award Travel Tools online. Get started today!


#awardyourmiles #awardtravel #travel #credit #creditcard #creditcards #creditcardrewards #pointsandmiles #hawaii #maui