Beginners Guide to Award Travel Planning - Award Flights Beginners Guide to Award Travel Planning - Award Flights

Beginners Guide to Award Travel Planning - Award Flights

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Following up our post on why travel goals are crucial to award travel success, we're back this time with an example of the planning process.

We’ve selected flying two people round-trip to Hawaii in economy for this demo. Our example is not business class, and it’s not an exotic jaunt to ancient Southeast Asian ruins; we’ve chosen it as a beginners destination for several reasons.

  • It’s still in the US, so you don’t have to worry about the added stress of visas and immigration, etc.
  • It's a popular destination, with multiple carriers flying from most US hubs, and economy awards are comparatively easy to find and affordable
  • Lots of accommodation options with chain hotels across a variety of rewards programs
  • You can access lots of guides from reputable sources detailing how to get there and where to stay
  • It ties into what we love about rewards travel. It’s a little exotic, beautiful, has great food, offers a wide array of experiences, and caters to a variety of demographics

Which Airline's Fly To Your Chosen Destination?

The initial step is discovering which airlines fly to Hawaii from the mainland US. The quickest way to tackle this is jumping on the Honolulu Airport (HNL) Wiki page. If you scroll down to ‘Airlines & Destinations,’ you'll find a list of the airlines that fly into HNL and the airports where those flights originate.


You can also use an online tool like to conduct this analysis, as they show which airlines/programs you can use, or, use Google Flights or if you prefer a visual representation of routes and carriers, but today we want to strip it right back to basics.

We can get to Honolulu on Alaska, American, Delta, Hawaiian Air, and United. Unfortunately, none of the US frequent flyer programs offer top value. Keep in mind, there are other islands with non-stop service from the mainland — don't forget them!

Which Frequent Flyer Program Is Best to Book Your Award?

Our go-to here is a simple Google search – ‘best points and miles for award flights to Hawaii.‘ If the destination is popular, Google will throw up a bunch of results. Look for articles that are current and up-to-date. You can filter your search using the ‘Tools’ button in Google's search console and select ‘Past Year‘ from the drop-down.


Here, we'll use our own post breaking down the best award programs for free flights to Hawaii. While US carriers offer flights, the legacy carrier frequent flyer programs don’t offer the best value. Here's where airline partnerships come in.

Instead, we can use:

  • British Airways Avios to fly from the West Coast (BA has a distance-based award chart) flying on partners Alaska or American for 25K miles.
  • Korean SKYPASS miles allow you to fly from anywhere in the US on partner Delta for 25K miles.
  • Or, for an extra 10K miles, you could use KrisFlyer miles to fly United for 35K miles or Alaska for 12,500 miles each way (must be direct flights).

This covers all three global alliances, so it doesn’t matter which alliance you’re loyal to.

Earning BA Avios is straightforward with the British Airways Visa Signature® Card. But you may wonder how on earth you earn Korean SKYPASS miles, or KrisFlyer miles when you live in the US? That brings us to another piece of the rewards travel puzzle: Which points should you collect?

What Points Will You Need to Book Your Flights?

You can transfer points to each of the above programs, including Avios, from Marriott Bonvoy, and to all except Korean from Ultimate Rewards. BA Avios also lets you transfer Membership Rewards points, and for Singapore Airlines, you can transfer all four flexible currencies to KrisFlyer, so you can also use Citi ThankYou Rewards.

Flying United using KrisFlyer miles may cost 10K more miles. But if you only had 10K points in each of your Chase, Amex, Citi, and Marriott accounts, you have round-trip flights to Hawaii.

This is the main reason we recommend focusing on transferable rewards currencies as the base of your rewards travel strategy. It provides flexible planning and tons of options to redeem your points for the greatest value. We’ve put together a table showing the difference in miles to get to Hawaii for the different programs. On the right of the table, it shows you which flexible currencies transfer into each program.

Rewards ProgramOperating AirlineEconomy
Transfer Points From
Miles & Smiles
• Capital One Miles
• Citi ThankYou Rewards
• Marriott Bonvoy
• Bilt Rewards
Rapid Rewards
Southwest12,500+N/A• Chase Ultimate Rewards
• Marriott Bonvoy
Singapore Airlines
Alaska Air23,000-25,00084,000-96,000• Ultimate Rewards
• Amex Membership Rewards
• Citi ThankYou Rewards
• Capital One Rewards
• Marriott Bonvoy
Korean Air
Delta25,00045,000• Marriott Bonvoy
British Airways
Executive Club
American, Alaska26,000(+)75,000(+)• Chase Ultimate Rewards
• Amex Membership Rewards
• Capital One Miles
• Marriott Bonvoy
• Bilt Rewards
Korean Air
Alaska, Hawaiian Air30,00060,000• Marriott Bonvoy
Air France/KLM
Flying Blue
Delta35,00060,000• Chase Ultimate Rewards
• Amex Membership Rewards
• Citi ThankYou Rewards
• Capital One Rewards
• Marriott Bonvoy
• Bilt Rewards
Singapore Airlines
United39,00078,000• Chase Ultimate Rewards
• Amex Membership Rewards
• Citi ThankYou Rewards
• Capital One Rewards
• Marriott Bonvoy
Hawaiian Airlines
Hawaiian Airlines40,000(+)80,000(+)• Amex Membership Rewards
• Marriott Bonvoy
• Bilt Rewards
United20,000+80,000++• Chase Ultimate Rewards
• Marriott Bonvoy
American Airlines
American Airlines25,000+80,000++• Marriott Bonvoy
• Bilt Rewards
Delta17,000+80,000++• Amex Membership Rewards
• Marriott Bonvoy
Alaska Mileage PlanAlaska20,000+40,000+• Marriott Bonvoy

Ultimate Rewards gives us options across a range of carriers and programs to get to Hawaii as does Membership Rewards and Marriott. Citi ThankYou Rewards only allows us to book through KrisFlyer and Flying Blue.

The least expensive choice is Korean or BA. Who you pick is typically determined by your location and the carrier you prefer to fly. Flights for two people round-trip will cost 50,000 Avios, Ultimate Rewards points, or Membership Rewards points. Or we can use 120,000 Marriott points as Marriott Rewards awards an additional 5,000 miles for every 60,000 points you transfer (60K Marriott points = 25K airline miles).

Learn more: Which Rewards Programs Allow You to Combine Points and Miles for Free?

Which Rewards Credit Cards Earn the Points You Need?

For flights we need:

  • 50,000 Avios, SKYPASS miles, or Ultimate Rewards points — or 120K Marriott points

Chase offers multiple cards that earn Ultimate Rewards and provided you hold a card that will transfer to partners; you can combine points earned from each card into one pool to transfer and redeem as you please.

The Chase Sapphire Preferred® Card, which we rate as the best beginners rewards card available, has a solid signup offer, or, if you own or operate a small business, you could apply for the Ink Business Preferred® Credit Card which offers 100,000 bonus points after you spend $8,000 on purchases in the first 3 months from account opening. Business cards are more accessible than most people think, almost anyone qualifies for a business credit card if you run even a hobby business or part-time gig.

You could also throw The Blue Business® Plus Credit Card from American Express into the mix. It tops our list of best credit cards for everyday spend earning a solid Earn 2X Membership Rewards® points on everyday business purchases such as office supplies or client dinners. 2X applies to the first $50,000 in purchases per year, 1 point per dollar thereafter..

Create a Spending Plan, Based Around the Points You Need to Earn

Developing a spending plan requires you to dig into the bonus categories of each card you hold to learn about category bonuses. You will also need to use shopping portals and apps like the Ultimate Rewards Shopping Portal to maximize points earned for all your purchases, and look at the opportunity cost of using services like Plastiq to get you over the line if you are close to reaching a travel goal.

If your goal is to hit an additional 30,000 Ultimate Rewards points, plan a realistic spending roadmap with a little wiggle room so you can jump on promos and shopping portal offers as they come to light. Use category bonuses, or offer to pay accounts or expenses for family members and have them reimburse you to help you reach your goals.

Final Thoughts

An achievable travel goal and a plan to earn the points and miles required to pull it off are just as important as the physical credit cards that earn the rewards while you first come to grips with earning and redeeming rewards points for travel.

Without a roadmap to achieve your travel goals, you will struggle to reach them and waste unnecessary time, money, and effort in the pursuit of your goals.

We plan on expanding this series in more depth over the coming months. If there is any subject you want us to dig into in more detail, please let us know in the comments.

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  • My biggest reservation/concern with locating, and transferring miles to purchase a award tickets is the
    Possibility that between the time I locate award availability and time needed to transfer points the award availability may disappear. Perhaps could address in a future post your suggestions, insight and “knowledge” how to maximize the process of locating, transferring points and successful making a award reservation.


  • Just getting into the travel hacks game. Ran a blog search for “beginners”. This popped up; and it is exactly what I was looking for. Bookmarking for future reference. Thank you for writing these “how-to’s” for those of us who are just starting to try to figure everything out!

  • Patty Hales says:

    The date on top says June 28, 2019. All of the comments come from 2017. What the post updated in some way? Is all of the info in it current?

  • Very comprehensible indeed. Yet it takes so much time and planning that often it is a lot easier to buy rather competitive airfare than use award tickets. Sad but true.

  • Jimmie Lin says:

    Sadly outside the US miles earning without flying is really hard! Hope you make an international series too to unlock the less-known deals outside the US.

  • I think two things which add value to points / miles are flexibility and having alternative.
    Flexibility allows you to redeem more easily for your favourite destination whereas having alternative allows you to have some plan B if something go wrong.
    This is even more true for families travelling together on high season.

  • Great article, but unfortunately for economy class traveler (leisure travel) from Europe reward flights are really hard to achieve, unless flying is part of your everyday business.

  • Hi,
    Any thoughts/suggestions on booking a business/first class trip to Hawaii, or is that essentially impossible?

  • It is very interesting to see just how many alternative ways to get to just one destination using points and miles. I tend to transfer my Membership Rewards to the same place, but this shows the value of keeping them until you need them for maximum flexibility. The article is also a very interesting demonstration of the use of pooling points from various sources.

  • I’m loving this new series Howie. Sometimes blogs tend to assume you’ve earned a lot of miles and redeemed a lot of them for flights and already know what to do. Many people don’t. Would love to see a follow up article on how to use points for stays/food/experiences once you’re there. Getting there and back is only half the challenge in my opinion.

  • Very good info. I am starting to plan an around-the-world trip, mostly southern hemisphere, and need to start planning.

  • angelo fonseca says:

    very informative. the best travel guide. thanks

  • This is a comprehensive overview that should be helpful for a lot of people. I think a good follow-up blog article could examine when is it better to use points/miles vs buying a ticket. For example, an Alaska Airlines sale to Hawaii combined with the free companion ticket (excluding taxes and fees) from the Bank of America credit card could make for an incredible deal.

  • Wish I had seen this when I first started it would have saved me some time, money, and precious pionts

  • For those outside the US these rewards are not available 🙁

  • Extremely informative article! Thx so much! What a treat to find applicable and helpful info all in one place! Mahalo!

  • Alice Chen says:

    This is awesome for beginners! It definitely is less complicated than it seems

  • One of the most helpful posts ever on a points and miles blog. Thank you!

  • This is such a great post and almost makes this miles and point hobby seem easy! I wish I had a reference like this when I had started out. I will be sharing this with skeptical family and friends.

  • Great things to consider. Does anyone else to their bookings through a partner airline? I tend to stick to American or United. Maybe it’s just fear of trying something new.

  • Any one know the best way to book award travel LAX to Peru??

  • lorem ipsum says:

    This is an excellent post for those getting into points and miles. I will be sharing it with friends and relatives, who keep asking me for details. This explains the basics better than I ever could.

  • Rob Arias says:

    Interesting, I have yet to book an award flight but good to see the process so thoroughly explained

  • Sebastian says:

    I tried to book an Award on LH with M&M – but the System always says “no Space on your Dates” – are there certain Route that don’t work?

  • Wow! This is a very informative article! I really appreciate the visual help.

  • Many noob mileage collectors overlook that 2nd critical aspect of spending miles efficiently.

  • Thank you for this series. Trying to figure out how to do reward flights is so difficult. I hope you do continue this series to move onto the intermediate and advanced techniques of successfully booking award flights to various international destinations.

  • Solid piece. Wish I had this when I was starting out.

  • Research, research, research is key in this game. I wouldn’t know half as much about miles/ points redemptions without great blogs like this.

  • This is a good workflow.
    Note, I think you meant OpenFlights instead of OpenFlight.

  • excellent advice for those just starting to enjoy the benefits of this hobby

  • Since comments seem to be turned off on the ‘importance of travel goals’ post, I’ll say it here: I can’t tell you how many times I’ve been asked by someone interested in getting into travel-hacking, “which card should I get?”. And the only way I can ever answer that is by replying with my own question: “where do you want to go?” I always tell newbies: one needs to start with a destination, and then figure out what the best pints currencies will be to get there.

  • There’s so much to consider, thanks for the smart grids and visual look at this. Most of us here have scratched down fifteen pages of notes when deciding how to book, where to book and which accounts work for us in any given scenario. This will be a big time saver.

  • Thanks! This is an awesome post I’ll definitely do some research on this for my next redemption.

  • This is one of your most informative posts, thank you!

  • Planning and research is key to getting the best trip experience and the best bang for your buck/points. Don’t burn those points or your hard earned $$ until you comparison shop….

  • This is such an awesome post! It just happens that I am planning a trip next spring to Hawaii. I’m bouncing back and forth between United and American. I’m looking for nonstop really but well, can’t be picky. But I’m unsure about all the transferring to SPG, etc. I think I might be looking at UR and book American, since they discount. I do admit I am curious about Hawaiian airlines.

  • This is exactly what I am looking for. Thanks for the writing!