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 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! Image courtesy of Southwest Airlines

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 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. 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! 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. Image courtesy of Hyatt

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