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How I Plan My Trips Using Miles and Points



In this article, I'll show you some of the websites I use to search for award flights, tips and tricks on how I plan my travel, and what credit cards you can use to boost your points and miles right from the start.


Maximizing Points and Miles with the Right Destination


Just because traveling right now isn’t easy doesn’t mean we can't start planning for future travel. If you're like me,then planning for your future trip is almost as exciting as the actual trip itself.


I don't plan my travel and vacations like a normal person would. I choose my destinations based on award flight availability. Whereas, someone might choose their destination based on a bucket list item. I’m Miles Miser, I try to get the most bang for my buck! I focus on finding First or Business Class flight awards and redeem them for points or miles, for fractions of what I’d pay in cash for the same flight.


One-Way Flights Can Offer the Best Value


I like one-way flights, they offer a little bit more flexibility and I can use multiple partner awards in one trip. I might find a one-way departing flight on a One World Alliance carrier and then I'll find a great return one-way flight back on a Star Alliance carrier.


For instance, I recently found a flight going out to a particular Island destination that I’ll be visiting in the near future. I'm going to be departing and traveling on a SkyTeam Alliance partner flight in a Business Class seat. It cost 120k miles and 60 USD in tax. If I’d paid cash for this flight it would have cost $4000! For my return flight, I found a Star Alliance First Class award flight through Aeroplan. That cost me 110k miles and $101.50 USD. If I’d paid cash for this flight it would have cost $7000! I will reveal to you those flights in upcoming videos, so subscribe and hit that alert bell, so you will be notified when I post. You don’t want to miss these flight reviews! You have to mix and match whatever flight awards work for you depending on what miles and points you have.


There are some exceptions, if you have enough miles and you're going to, let’s say Narita (NRT) or Haneda (HND) Airport, you can book a round-trip Business or First Class award ticket on ANA for typically less than what you would pay for a one-way trip. You can book for around 120k to 130k points for Business or First Class. Some carriers only allow round trips. Make sure to check out the rules of your carrier and go from there.


Book Trips Far in Advance OR Last Minute To Get the Best Deals


The best policy is to start looking as far out as possible, up to one year. To book my trips, typically I have been looking as far out as one year to six months in advance. In the new year, airlines will start releasing award ticket availability, so you want to get on the ball and see what's out there as soon as they release the flights. Also, check every couple months.


However, another option is booking last minute. Sometimes airlines only release First and Business Class award availability a week to two weeks, maybe even two days, before the flight. If you have more flexibility within your personal schedule, you might score an awesome last minute First Class flight internationally like I did, for my Japan Airlines flight the last time I went to Asia. Two days before the trip I found the First Class flight for 75k Alaska Airline miles one-way.


Booking Flights Using Points and Miles in 4 Steps


Step 1. I first think about the places or countries I'd love to see.

I pick three or four destinations from that list. Then I find the months that are good to travel and visit those areas based on the weather or off-season travel. I find out what airlines fly there.


Step 2. Research Your Destination Accommodation Options.

I check to see if there’s a resort that I can use points to stay in, or maybe even an Airbnb. Basically, I make sure there are plenty of accommodation options.


Step 3. Take inventory of all your points and miles.

Know how many points and miles you have available in all your different programs.

I take inventory of what points or miles I currently have and in what programs. I keep this in mind because certain credit cards from Chase, Capital One, CITI, and Amex, have the option to transfer points to different airlines directly. This makes those points flexible and valuable. I look through the various partner websites (OneWorld, SkyTeam or Star Alliance) for award availability depending on how many miles or points I have in that particular program or what points I can transfer from my various credit cards.


Step 4. Then I go about the tedious process of finding award availability.

I use the following websites for searching award availability. There’s a ton more but these are my goto’s. It’s a long process but it’s worth it!

  • British Airways for OneWorld.

  • AeroPlan go to for Star Alliance

  • Delta and AirFrance for SkyTeam

  • ITA matrix and google flights if I'm paying in cash.

  • NOTE: You have to have an account and be logged in to search on BA and aeroplan!

I look during the different months I've already researched in Step 1. I’ll look at the major hub airports around where I live, like the New York area (LGA, EWR, or JFK), and if find any awards I may have to look for flight leaving from Boston (BOS) or might even have to go to Chicago (ORD) and look from there. This goes on, until I find a great award or exhaust my search for that particular month, then I start over on a different month or a different destination.


If you live on the West coast, check your respective airports like San Francisco (SFO), San Diego (SAN), and Seattle (SEA). Don’t forget other Midwest hubs like, Detroit (DTW), and Minneapolis (MSP) and southwest like Dallas (DFW). These are some of the major hub airports. You should also check your local airports because sometimes you can get connecting routes to a major hub airport near you and these might show award availability whereas going directly from a major hub wont.


You have to find a way home, so make sure to reverse your routes and see if there are award flights flying back home too. In reality, it takes a lot of time and effort to find these award flights, sometimes you give up on a particular city or that place you want to go and start over.


The Best Award Redemptions I Have Found


It all depends on luck but I try to be diligent and search all the time. Alaska Airlines have been really good to me. I've scored two First-Class International JAL flights for 75K Alaska miles each with under $75 USD in taxes. Those flights would have cost $10K-$16K per person one-way, and I scored not 1 but 2 one way tickets on two different occasions!


Another program I’ve had luck with is Aeroplan, because it has so many Star Alliance Partners. Unfortunately, they just did a revamp of their program and I noticed that many of it’s First-Class awards are non-existent and can’t be found anymore. At least that's what I'm seeing at the time I'm recording this but that may change in the future. Although, it now costs a little bit more miles for the same trips because they restructured their program, overall it appears to have a plentiful. They did reduce some of the fees that are associated with the redemption of award flights, such as carrier fuel surcharges and taxes. What’s that you ask? Airlines pass on fuel costs and fees in their tickets to the person flying.


American Airlines has good award redemption for their partner Airlines through One World. Cathay Pacific and JAL are One World partners. For instance, you can score a one-way First Class award from JFK to NRT on JAL for 80k AA miles! That's a really good Redemption.


Redemption for partners airlines usually go off the partners award chart. That means that an award chart redemption on a partner like Cathay Pacific would reference American Airlines partner award chart and that's how many miles it will take in American Airline miles to book that fight.


That's why you have to be flexible and have a miles and points stash stockpile, it helps to have American Express, Chase, Citi or Capital One cards which generate points that are transferable. That means that you can transfer those points to a particular Airline or award program when you find a great award.


Airlines have been devaluing their miles programs a lot lately. For example, Delta devalued their Skymiles program twice within the last 6 months. What does that mean? That means it takes more miles to get the same flight than in the past.


Best Bang for Your Buck: Domestic or International Flights?


If you want to use your points or miles for domestic travel, there's nothing wrong with booking short trips domestically in the US. Although for me the best miles award redemption is going to be had by booking international flights.


Ask yourself this, would you rather sit on a First Class transcontinental flight from JFK to San Francisco, typically it's only a recliner seat, and costs like 25K - 50K points or miles, or would you rather fly 14 hours in a fully lie flat Business Class suite with a great big entertainment screen, pillows, great food and all the champagne you can drink flying to Japan or Bangkok for 50k miles or 75k miles? To me it's a no-brainer, Namaste in first class tyvm! I’d rather be in a First Class flight eating steak, and caviar and sipping champagne for 14 hours that I paid for with miles.


Sure you do earn those miles and points on your credit card spending and that takes time. But ask yourself this, are you ever going to pay for that trip out of pocket when it costs $10K-$20K? No, not me, I can't afford that. That's why I have to leverage points and miles to fly on these flights. So that's what I do!

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