How to Fly Roundtrip to Hawaii with a Stopover for 25,000 Points!

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I wrote an earlier post on Hawaii award redemptions when I first discovered this particular loophole.  When I wrote about it, I was simply presenting the basic strategy, because we had not yet booked our trip.  I am happy to report that we now have an AMAZING trip on the books – including two days in Sonoma Valley and thirteen days in Hawaii!!!  Our entire roundtrip flight cost only 25,000 points + $33 per person!!  Read along to find out how we did it… 

This strategy is alarmingly simple on the surface, but requires just a bit of effort to pull off.  This article specifically addresses roundtrip economy award tickets for 25,000, but you can also book roundtrip first class tickets for 45,000 each.  I’ll break down the process in steps.:

Step 1:  Acquire 25,000 Transferrable Points (per person)

There are three very efficient options to grab these miles.

Option 1 – Chase Sapphire Preferred Card

sapphire_preferred_cardThe Chase Sapphire Preferred card comes with a 50,000 Ultimate Reward (UR) Point bonus + 5,000 Points for adding an authorized user.  To earn this bonus, you will need to spend $4,000 in 90 days.  With this bonus, you will have enough for TWO ROUND TRIP TICKETS!!  Chase UR points convert directly to Korean Air Skypass miles at a 1:1 ratio, and the transfer is instant.

Option 2 – Chase Ink Plus Business Card

ink_plus_cardThe Chase Ink Plus card comes with a LIMITED TIME 60,000 UR Point bonus!  This will be more than sufficient to get you and a companion to Hawaii.  You will even have 10,000 points left over if you need to top up your Hyatt account for a hotel while you’re in the islands!

Option 3 – American Express Starwood Preferred Guest (SPG) Card


The Amex Starwood Preferred Guest card and Starwood Business Card both feature a bonus of 25,000 SPG points. To earn this bonus, you must spend $3,000 (or $5,000 for the business card) within 90 days.  American Express recently announced Korean Air as a new transfer partner for Starwood Preferred Guest (SPG) points.  When transferring SPG points to airlines, you will receive an extra 5,000 miles for every 20,000 points you transfer.  Transferring 20,000 SPG points = 25,000 Korean Air miles!

If you do not use your SPG points for Korean Air miles, they are great for booking free nights in Hawaii.  We booked 5 nights at the Sheraton Kauai Resort for 48,000 Starwood Points!

Step 2: Create a Korean Air Skypass Account

Korean-Air-logo_white-backgroundOnce you have earned your Chase UR or SPG points, you must create a Korean Air Skypass Account. Register for an account here.  Korean Air also allows you to use your miles to book tickets for immediate family members.  If you plan to do this, your family member will also need a Skypass account.  Once they create an account, you must submit a Family Registration Application.  According to the rep, the online application is processed much more quickly than the paper application.  Mine and Brooke’s family application required us to scan a copy of our marriage certificate for proof.

Step 3: Find Award Seats on Delta

Yes, you read that correctly.  Delta is a sky team partner with Korean Airlines, therefore seats on Delta flights can be booked using your Skypass Miles.  Head over to Delta’s website to locate the flights you want.  You must have a sky miles account to view award availability, so go ahead and create one.  When you search, make sure you select “Show Price in Miles.”  To see which seats that Delta is making available to partners, you may want to do an award search on Air France or Alaska Airlines.

This is where it gets fun!  Korean Airlines has pretty generous routing rules.  They allow one stopover (connection lasting more than 24 hours) en route to your destination and one open jaw (fly into and out of different airports) at your destination.  All segments must be booked on Delta flights, because Korean Air does not allow multiple partner airlines to be booked on the same itinerary.  I chose to create the following itinerary:

Screen Shot 2015-08-06 at 3.48.10 PM
Price in $$ – Incredible Redemption Rate of 4 Cents/Point!!

MCI –> SFO (2 day stopover) –> LIH…(open jaw)…OGG –> MCI

Screen Shot 2015-08-14 at 11.56.57 AM

When you search for a route, you do not have to use these exact cities.  You can schedule your stopover in a completely different city, and you can use different islands for your open jaw.  Use the Multi-City search function to play around with routes.  Other possible itineraries could be:

ORD –> SEA (4 day stopover) –> HNL…(open jaw)…KOA –> ORD

JFK –> MCO (3 day stopover) –> OGG…(open jaw)…HNL –> JFK

As long as your route follows these rules, and delta shows award space at the saver level (45,000 – 60,000 Skymiles), you should be able to book the round trip for only 25,000 Skypass miles!  Write down the specific details of your itinerary, including flight times and numbers for the next step.

**NOTEYou MUST find your own transportation to complete the open jaw portion of your trip!  More on that in Step 7.

Step 4: Call Korean Airlines to Hold Your Itinerary

Now that you have an itinerary selected, and you have taken thorough notes, you need to call Korean Airlines at 1-800-438-5000 and speak to an agent.  The agent will take down your selected itinerary and schedule a call back from a booking agent within 24 hours.  If you ask nicely (especially if there is limited availability on your routes), they may be able to transfer you directly to the booking agent.

The booking agent will use the information you provided to determine if the seats are actually available.  It took me three calls to the booking agent before my itinerary was finalized.  On the first two calls, they had no availability on my flight of choice.  Sometimes this happens, and you must be willing to adapt.  Simply thank them for their time and re-work your itinerary.  They will also confirm whether your selected itinerary is within the Korean Air routing rules.  If everything checks out, they will hold your itinerary while you handle the next steps.

Step 5:  Transfer Points to Korean Air Skypass Miles

At this point, you will need to transfer the Chase UR or SPG Points that you earned in Step 1.  Chase UR points transfer to Korean Skypass Miles at a 1:1 ratio and transfer instantly.  SPG Points transfer at a ratio of 1:1.25 if you transfer in increments of 20,000 points and can take a few days.

Step 6:  Submit the Award Application Form

The final step to booking your ticket is to submit the Award Application Form.  You will need to fill out the form, print, and sign it.  Then, scan and email the form and a copy of your passport(s) to  If you are booking tickets for your immediate family, they must appear as family within your Skypass account (see Step 2).  If you plan to travel with people who are not immediate family, each passenger must submit this Award Application Form, and book with miles from their own accounts.

When your application has been accepted, you will receive a call from a Korean Air representative to collect the taxes of $11 per segment.  After paying, you should check back within your Skypass account under “my trips.”  Look for international tickets, and your tickets should appear within a few days.  Congratulations, you’re going to Hawaii!!

Step 7:  Complete the Open Jaw (optional)

If you chose to include an open jaw in the Hawaiian islands, you will be responsible for getting from your arrival airport to your departure airport.  For our trip, we land at LIH, and depart from OGG.  To close the jaw, we are using American Airlines miles to book island hopper flights on Hawaiian Airlines.  Simply search for the flights on American Airlines’ website.  They only cost 5,000 AA miles per segment (4,500 if you have the Citi AA Platinum MasterCard)!  We are flying LIH –> HNL –> OGG using this method.

Screen Shot 2015-08-14 at 11.57.42 AM
Use AA miles to “close the jaw.”

I hope this guide has been helpful to book your dream getaway to Hawaii!  What route to Hawaii will you choose??  Check out these links for a full review of our experiences in San Francisco/Wine Country, and our Complete Guide to Hawaii.  Cheers!

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68 thoughts on “How to Fly Roundtrip to Hawaii with a Stopover for 25,000 Points!

  1. I’ve been looking for a post from someone who actually did this for quite a while. Thank you and I’m glad I found your site! I’ll be working on a hawaii trip over the next few weeks or so. Hopefully I can grab some flights via koran air.


  2. Would this same logic apply in traveling the 80k award ticket to Asia? Wondering if you could do a flight from Detroit to Honolulu (stopover flight) then leave Honolulu to Chiang Mai (Open Jaw) with Bangkok to Detroit. or is that an extra segment?


    • You would need to call to confirm that your routing fits all of their rules, but I would assume this sort of routing will work. I have not delved too deeply into their international flights.


  3. Do you also have to create a Korean Skypass account for each of your children even if they are minors just so you can book a flight using your miles? Also create an account for the spouse? Thank you


    • For your family, you should be able to create and book with one master account. You will have to prove that you are indeed a family. I am honestly not sure how that works with children.


  4. […] Just like the flight from Kauai to Oahu, we used 4,500 American Airline miles to book island-hopper flights on Hawaiian Airlines.  These flights are available on for 5,000 AA miles, and we got a 10% rebate because of our Citi AA Platinum cards.  Availability was a bit spotty for award seats, but we were able to make it work with some careful planning.  If you can’t find award seats, the flights are inexpensive at $80-$100.  Our return trip to Kansas City was covered as part of the open jaw on our Korean Air booking. […]


  5. Why would you need to send in a copy of your passport as this is a domestic trip. I’m trying to get my sisters on slc-hnl round trip and neither of them have passports. Thanks.


  6. So am I looking for where Delta is charging 45K miles….that is how I know it is the lowest level so I can book them on Korean for 25K?


    • Your best bet would be to search delta and find the least expensive option, and then call Korean to check availability. They will be able to tell you pretty quickly if they see the seats.


  7. quick question:
    Would it be smart for my husband and I to BOTH get chase SP cards rather than for me to get the 5k bonus miles as an add on to my card?


  8. Great article. Did some research and have a quick question Jesse. Would the below be possible for 25K miles Roundtrip. Or am I assuming something wrong here?

    BMI-SFO(3 day StopOver) – SFO-OGG(Open Jaw) – LIH-BMI

    When I see this itenary for a set of dates in April, Delta shows 110K miles. I am afraid if I am missing something. Thanks for all your work.


  9. Quick question. You mentioned in your original post to depart from your closest airport to Honolulu. Will this work to fly into OGG or can I just fly into HNL?

    Basically I want to know if this will work for flying from DEN to OGG.

    Also, do layovers affect any of this?



  10. “As long as your route follows these rules, and delta shows award space at the saver level (45,000 – 60,000 Skymiles), you should be able to book the round trip for only 25,000 Skypass miles! Write down the specific details of your itinerary, including flight times and numbers for the next step.”

    Can you explain this a little more? Thank you.


  11. […] Unfortunately, in a space where the lines between advise and selling are often very blurry at best, we see far too many rah-rah-look-at-my-shower-in-the-plane-you-can-do-this-too-if-you-click-these-three-links-it’s-easy!!!!  posts that pay little or no attention to the dangers and difficulties involved. Not to pick on Jesse, but an example of this on Loophole Travel gives these specific steps: […]


  12. Hi Jesse I had a question about step 3. You say to show price in miles on the Delta website. When I do so the miles are way more than 25K, closer to 60K. Does that change things? Or does Korean charge 25k miles regardless based on their SkyTeam table?


  13. Hi Jesse, Thanks so much for your post. It is very helpful. I am looking at DEN>LAX>HNL but is pricing out at 75k Delta points. 25K DEN>LAX and 50K LAX>HNL. If using Korean Air would I still be able to book (F) for 45K points?


  14. Is this loophole still usable? We are looking to book 4 flights from Columbus Ohio to Kona Hawaii over thanksgiving of this year. I have 70,000 points on chase sapphire and can easily get it to 100,000. i created an account with delta and korean air but am a little stumped on what to do next. I couldn’t see anywhere on Korean Air’s website where it says they only charge 25K award points for partner flights. can you direct me?


  15. Hi Jesse, any idea on when DL releases the saver level awards i.e. within 7 days of booking, a month, etc. ? Not sure if I should spend time looking for flights that are <21 days out or not.

    Also, in order to get KE to book @ 25k miles, do I have to use the multi-city search? I want to use the flexible date function, but that's not available with multi-city, so is finding a bunch of one-ways legitimate?

    Where did you find saver level=45-60k? I tried Googling for another source on that claim, but couldn't find anything.

    My ideal itinerary would be RIC-SFO (stopover)-KOA-HNL(open jaw)-RIC


    • I’m really not sure how they handle the availability. Since their prices aren’t consistent, it’s probably worth your time to call Korean Air and ask if they see anything around your dates.


  16. After I originally commented I appear to have clicked on the -Notify me when new comments are added-
    checkbox and now each time a comment is added I receive 4 emails with the exact same
    comment. Is there a means you can remove me from
    that service? Thanks!


    • I can’t seem to find where you commented before. I was trying to go back and delete your old comment, thinking that may fix the issue. You may need to contact WordPress support, because I don’t think this is something I have control over. Sorry about that!


  17. This has been very helpful but would love advice on booking the entire trip for my family of 5. We are looking to go from New Orleans to Honolulu with a stop in San Francisco on the way for a total of two weeks. I have 110k Chase Saphire points, 42k SPG points, 100k Hilton points and 100k southwest points at the time. We are looking to go Summer 2017. How can I maximize the points I have as well as what do I need to do to cover all hotel and rental car expenses on points.


    • Hi Lori – Award booking complexity goes up significantly when you add more people. Finding five award seats on a single flight with a stopover at the Delta saver level, during prime travel season, will be a challenge. Your point balances will enable you to book these fights if there is availability. For hotels, look at Award Mapper, and car rentals you got use the Chase UR portal.

      We offer personalized award travel consulting, but this is a very complex situation.


      • Thank you. Do you find that it is better to book award seats as early as possible or should I wait until it’s closer? Also I am rethinking the hotel and found some great condos on the beach on vrbo. What would be the best credit card to use when booking vrbo?


      • Always best to book early, especially with 5 people. If you have a Barclay Arrival+ or Capital One Venture, you can redeem those miles against the price of the VRBO.


  18. Hello!

    I’m hoping you can help me. We are leaving on an Alaskan cruise from Vancouver 5/29/17 and I would like to tack on a week in Hawaii. My problem is that I would like to see Hawaii before the cruise…

    We live in the Midwest near Sioux Falls (FSD). Is it even possible to route FSD-LIH-SEA-FSD? I have found award availability FSD-LIH and SEA-FSD but I’m afraid the Korean miles won’t work since it’s not FSD-SEA-LIH-FSD.

    Any help you can provide would really be appreciated. I have loads of miles in multiple programs but the redemption part is CONFUSING!!

    Thank you!


    • The routing you found should be valid, with LIH-SEA being the open jaw. You would need to find a separate flight to fill the gap. You can search Delta or Alaska airlines for availability. The whole itinerary must be in a single airline and conform to the Korean routing rules. We offer personalized Award Travel Coaching services to assist with booking complex itineraries like this.


  19. Thought I would let you know I was able to book 7 round trip tickets from MSY with a stopover in LAX then on to HNL round trip for 175,000 miles. Have you ever tried to pay for a first class upgrade after the fact?


  20. what is the best way to handle the baggage fees from Delta, is it worth opening a Delta credit card to get one bag free for all of us or is another credit card a better option?


    • I highly advocate not checking any bags. It will make the whole process much smoother and more efficient. If you absolutely do not want to pack light, the delta card could be a good option.


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