How I Booked $20,000 Tickets for $362.80 with Travel Hacking

How to fly for free using travel hackingOne Sunday back in July, I booked two tickets that would have cost more than $20,000 total, but only paid $362.80. I’m also flying first and business class to Sydney and Bali on one of the best airlines in the world, including one flight with our very own suite.

I can’t wait!

You too can be flying for cheap and even in first class if you want. I’ll tell you how in this post.

Booking this ticket was one of the more spontaneous things I’ve done. That morning I had no plans to book a ticket, but by the end of that day, I had two tickets for next February.

However, I had begun preparing for this kinda of opportunity just about a year ago when I found my favorite new hobby.

If you’ve ever thought about taking your dream trip or traveling the world for free and in style, you’re going to love this post.

Cashback = Not the best deal

I knew about earning miles while flying as long as I’ve been flying, but didn’t know too much about earning it from credit cards.

I’ve had credit cards and I thought I was getting a great deal getting 1%-5% cash back. I thought if I spent $1000, getting $10 was awesome!

Better than nothing, but not maximizing the opportunities out there.

Last year, I started reading about people booking free airline tickets, often in first and business class, all over the world with points from huge credit card bonuses. Trips that would have cost thousands of dollars. That’s the type of award I wanted to get. Not cash back.

I love to fly. I like just being in an airport. I get exciting knowing I’m flying somewhere.

However I’m not a millionaire, so I can’t pay full price for first class seats. I had learn more about travel hacking.

I realized I used my credits cards often, but instead of cash back, I could be getting so much more out of them.

That’s when I began to learn the world of collecting points and miles and I’m loving it.

My First Airline Credit Card

Last year in August, I signed up for my first airline credit card, the Alaskan Airlines card that gave me 40,000 points and a certificate for a companion ticket for only $99. I just had to be approved to get the benefits.

That means I could book a ticket anywhere Alaskan Airlines flies and my companion ticket would only be $99! That ticket could even be to Hawaii! Who wouldn’t love to go to Hawaii for $99?

That’s the kind of deals airlines are giving away if you sign up for their credit cards.

Since then I’ve signed up for eight more credit cards, done mattress runs and have earned easily over 500,000 airline and hotel points which I have used to redeem for free hotel night and airline tickets.

In July, Eleanor and I went to California for 10 days and 9 nights. We started in Santa Barbara and drove the Pacific Coast highway to San Francisco. We spent four nights on the road and then five nights in San Francisco.

We only paid for one night in a hotel the whole trip.

The other nights I used hotel points I had earned to redeem free nights in different hotels. We stayed at the Hyatt Santa Barbara, which was right across the street from the beach. In Monterey, we stayed at the Marriott with views of the ocean.

In San Francisco, I used points to stay at the Radisson at Fisherman’s Wharf. When I checked in, they upgraded us to a room with a courtyard view and standing on the balcony, got a view of Alcatraz.

How we booked the Radisson Alcatraz for free

I can almost swim there

The last two nights, we stayed at the Le Meredien in San Francisco. Since I have gold status with Starwood, I got upgraded to a room with a view of the city and bay. Two nights there would have been $900. I used points from signing up for their credit card. First year no annual free.

How to booked the Le Meridien San Francisco hotel for free

View from our room

I added our hotel stays and we saved at least $2,000.

I’m definitely not an expert in this area. There are many more people out there who know the system better and how to maximize the number of points they can get.

However, I learned enough to be able to get free hotel stays and airline tickets and I know you can too.

How I Got So Many Points

Among my many credit cards, two are the Chase Sapphire Preferred and the Chase Ink Bold.

When I signed up for them last year I got 50,000 points for the personal version and another 50,000 for the business credit card. (Now the bonuses are 40,000 each)

You can do a lot with 100,000 points. Free airline tickets. Free hotel stays.

I would receive those points when I spent $3,000 in the first three months for the personal card and $5,000 for the business card.

That may seem like a lot, but when I’ve needed to meet the minimum spend I’ll put everything on that card. If you don’t spend that much, here is a great blog post that gives you 45 ways to meet your minimum spend.

I just spent normally too. I didn’t buy stuff I didn’t need just to meet the minimum spend. This is important because you might think I spent like a crazy fool.

Far from it.

Also the Chase Sapphire Preferred card has 2x points for travel and dining. So anytime we went out to eat or bought a plane ticket, I charged it to the card.

For the business credit card I was paying for work on Photo 365 and Gratitude 365 so I charged it to the credit card.

In about nine months, I had already accummulated 200,000 Ulimate Reward points alone. And if you’re doing the math, I’ll just say I definitely didn’t spend $100,000 to get the other 100,000 points!!

I took advantage of bonus points offers from Chase to get as many points as I could, while spending normally.

Putting My Travel Hacking Skills to Work

It was a Sunday morning and I had no desire to book any trips. Since I do follow travel blogs, I did see about a glitch in the United website’s booking system. There was a lot of excitment over it, but I didn’t think much about it.

Singapore Airline is one of the top airlines in the world. The service in first class is consistently rated the best in the world.

The reason travel hackers were so excited was because typically Singapore Airlines only allows reward booking through their website. You have to use their own frequent flyer points to redeem as well. Also they don’t open up availability until closer to the travel dates.

That makes it tougher to get a free ticket on Singapore.

However, their reservation system was down so for that weekend and for some reason all reward tickets were available through United’s website, which is a Star Alliance partner with Singapore Airlines.

They rarely release award space to alliance members (i.e. United), but this weekend everything was bookable. They were available months in advance as well.

This was the stars aligning perfectly! People were going crazy and booking tickets.

I kept reading the what exciting itineraries people were booking and I thought maybe I could take advantage of this with all these miles I’ve been collecting.

(Note: Here is the post that I learned about that limited time opportunity. 441 comments! Also Ben wrote a FAQ about it if you want to read more about why it was a big deal.)

For a long time I had so many Chase Ultimate Reward points and I hadn’t redeemed them for anything. I felt like a hoarder!

I easily could have booked free domestic flights or hotels. But my goal has been to book a free ticket for an international flight in first class.

I wanted to go big when I finally redeemed them.

This was my opportunity.

Planning the Itinerary

I decided to start looking for a trip we could take.

I thought about flying to Sydney, Australia since Eleanor and I have been wanting to go back since we lived there for a few months in 2008-2009.

I searched to see what was available. I briefly told Eleanor what was going on. She thought it was a great idea, but maybe we could leave from Taipei and take her mom too.

Next Februrary she’ll have a week off work because of Chinese New Year. She’s always wanted to take her mom to Sydney. Though I didn’t have enough points to book free tickets for all three of us, she said that’s okay. Her mom could just fly on another flight and meet us in Sydney.

So I looked for tickets starting in Taipei.

Then I thought let’s not just go only to Sydney. That’s too boring. Plus adding more stops wouldn’t cost any extra points.

She loves Bali and is always talking about going back since we were there in April 2011. That’s where I proposed to her. 🙂

I decided we could fly to Sydney, stay a week with her mom, then another week after her mom left. Then we would fly to Bali and stay for almost two weeks. Finally we would fly back to Taiwan.

A great plan.

I searched for hours for the best flight with the most first class seats. The itineraries came with with a mix of business and first class. I think I waited a bit too long so I couldn’t get all first class seats. That’s okay though because I could live with first and business class.

I checked different days just to make sure I covered all possibilities.

I probably spent 4-6 hours just searching, but it was exciting.

Finally I found the best itinerary for our trip.

On United, I had about 77,000 miles through probably a lifetime of flying. I had never used it to book a reward ticket.

I needed 260,000 points for two tickets. I had 200,000 points in my Chase Ultimate Rewards account. Whew! I’m so glad I had been hoarding so many points for so long!

The great thing with Ultimate Reward points is that they transfer to many airlines and hotels, including United. That’s why Ultimate Reward points are arguably the best right now. What’s even better is they transfer instantly. I just logged in and said how many points I wanted to transfer.

Once my points were in United, I quickly booked the ticket and paid $362.40 in fees. Done!!

It did give me the option of just buying both tickets for $20,000!! Let me think about that…hmmm… thanks.

Just writing about this post makes me excited about our trip. We’re flying a mix of business and first class, but our three longest flights will all be in in first class.

I was so excited in booking the ticket that I didn’t care that we have to take three different flights to get from Taipei to Sydney. That night Eleanor reminded me that if we flew direct from Taipei to Sydney it would take 8.5 hours.

The ticket I booked would take us 28 hours to get there. Our layover in Beijing is 7 hrs 55 mins alone! Crazy? Yes, but we’ll be able to wait in the first class lounge and flying first class will make it much more exciting!

Here’s how our trip looks.

Our trip and how to fly for free

Singapore Airline’s Famous A380

I even got an amazing surprise three weeks after I booked the ticket.

I remember when I first heard about the A380 first class suites back in 2007 when they started

It takes flying first class to a whole different level. It’s not just a big seat, but it’s an actual suite with doors for privacy. The seats don’t turn into a bed. You sleep on an actual standalone bed.

Luxury in the air!

Seats were tens of thousands of dollars at the beginning.

You can’t use points to redeem for a suite either. You can only purchase a seat. However there is a way around it with some luck.

After I booked this ticket, I read if you’re booked in first class and Singapore changes the plane to an A380, you get moved into the suites!

One day I went to Singapore’s website check our seat assignments and noticed one leg of our trip was upgraded to an A380. What?? A380? I had to look a few times to make sure it said A380 and not the original 777.

It wasn’t a mistake.

That means we’ll be flying in the suites!

How to fly for free in the Singapore A380 Suites

The bed in the Singapore A380 suites

It’s our flight from Singapore to Tokyo on the way back home. So we’ll have 6 hrs 45 mins to enjoy the suites. Not long enough, but still amazing! It’s a redeye flight so it’ll be nice to sleep on a real bed. I may not want to leave the plane.

I check Singapore’s website to see how much booking a suite would be for that flight. It would be $8,949.44 for two seats. If I divided that by seven hours, that’s $1278.49 per hour for the two of us!

Talk about getting even more value out of this reward ticket.

Anyone Can Do This

The beauty of collecting points and miles is that anyone can do it. If you love to travel, but feel like it costs too much, this is something you should look into.

(Note: Anyone can, but not everyone should. If you cannot pay your credit card bill in full every month, then don’t sign up for a bunch of credit cards. The interest you would pay isn’t worth it.

Also if you’re about to take out a big loan for a house or car, you may not want to sign up for a bunch of credit cards too close to it. The reason is every time you sign up for a credit card, your credit score takes a hit. Just wait.)

If none apply to you, I would look into sign up for credit cards and get those bonuses!

Double the Rewards

I could have had more points. How?

If my wife was eligible to sign up for credit cards, I would have signed her up and gotten more points and more rewards.

Unfortunately, we were waiting for her green card so she wasn’t able to.

You can easily have your boyfriend/girlfriend/husband/wife/partner sign up for credit cards as well and combine your points and rewards.

Here is a great example of how you can double the bonuses.

I signed up for the Hyatt Visa card. After my first purchase, I can get two free nights at ANY Hyatt in the world.

We’re looking to use two nights at the Park Hyatt in Sydney next Februrary. A quick check at the rooms show they’re going for $1,040 a night!!!

Park Hyatt Sydney

Now if wife could have signed up, we would have four free nights total to use. That would be $4,160 in value!

There is an annual free of $75, but when I signed up there was an offer to waive that fee after my first purchase. Still I’d easily pay the annual fee to get two free nights at a room like that.

The cool part about it is if I can do all this, you can too for sure.

Join the Travel Hacking Cartel

Travel Hacking Cartel. How to fly for free

If you want to learn how to do all this, you can join the Travel Hacking Cartel which is run by Chris Guillebeau. I’m going to assume most of you know who he is, but if you don’t, he is a blogger, author and travel guru.

He’s only six countries away from visiting every single country in the world. That’s an amazing achievement!

He’s gotten many of these flights for free from travel hacking and this course teaches you exactly how to do it.

Tutorials get you started and teach you everything you need to know. It gets straight to the point.

Then you get text + email alerts when there is a great deal. That saves you time from searching forums and blogs for a limited time offer.

There are different plans.

  • Economy Class ($15/month): Economy class level will feature email and text alerts, the full suite of travel hacking tutorials, as well as sweet, sweet deals on airline offers.
  • Business Class ($25/month): Business class features everything that the Economy class does, but will also feature awesome deals on hotels as well.
  • First Class ($39/month): For the ultimate travelers, this will feature everything the first two have, but will also be offering (and be oriented towards) high end travel hacking deals.  Getting the luxury upgrades, flying first class etc.

Try it out for 14 days for only $1. Only one dollar. That’s pretty much no risk. Sign up and go through membership. Stay as long as you need. Cancel anytime.

When you do join, you have his 100% guarantee. If members follow the directions and spend at least 30 minutes a month travel hacking, they’ll earn enough miles for at least 1 plane ticket every three months, or 4 plane tickets a year (he also provide info on how to redeem miles for great awards).

Join the Travel Hacking Cartel for just $1 now and learn how get miles to see the world

Forums Are a Great Resource

In addition to the Travel Hacking Cartel, you could find a ton of discussion going on about travel hacking.

FlyerTalk is the granddaddy of all travel forums. So much information can be found there. It can be a bit overwhelming for a beginner, but it’s the best.

Often they’ll talk in airport and airline codes so it’s like another language. No worries because there is a page that gives you all the meanings.

Do a search if you have a question and likely it’s been answered before.

A new one is Mile Point. A great place for beginners to ask questions and get answers. The general vibe there is more friendly.

Travel Hacking Blogs

If you have a lot of time on your hands and rather learn on your own, you can learn from reading blogs. It’s harder because they mostly will write about the latest deals, how to meet the minimum spend, or anything related to travel hacking.

Blogs I love to read are:

Also check out, which hosts a bunch of great travel bloggers. I’m always there a few a day scanning the headlines for deals and tips.

That’s how I found out about the Singapore Airlines reward ticket.

No credit cards? No problem

If you don’t want to sign up for a bunch of credits or cannot, you can still get in on the fun.

Hotels will often have promotions that give you rewards for staying at their hotel.

Radisson has one of the best.

When we went to San Francisco, we stayed at the Raddison at Fisherman’s Wharf for three nights. I could have booked five nights, but they only had availbility for three nights. When we checked it, we got upgraded to a courtyard view room. From the balcony, we had a view of Alcatraz.

If we paid for three nights, it would have been $900, but we paid way less than $300 for it.

A fantastic deal in my book.

We did what is called a “mattress run”. Last winter Radisson had a promotion if you stayed one night at any Radisson you would get 50,000 points redeemable for one night at their top properties around the world.

Free nights start at 9,000 points a night.

What people were doing, including me, was staying at a local Radisson where rates were much lower. Then use the points earned when a room is needed at a much higher rate.

In Jacksonville, we have one Radssion and the rates when we stayed were anywhere from $80-$100. I even got Eleanor to sign up. She must have thought I was a bit nuts when I said, “I’ve booked a room at the Radisson, but we’re just going to check in and not stay overnight.” Thankfully she understood the benefit. So both of us booked a room at the Radisson on different nights. I searched when it would be the lowest.

We got an easy 100,000 points.

Radisson did it again earlier this summer. This time they included their other property, Country Inn and Suites. One night stay there would yield an easy 44,000 points.

Just to give you an example of what a great deal that is. If you wanted to go to Disney World with the family, and you had 44,000 points from a one night stay at your local Country Inn and Suites, that’d get you four free nights at 9,000 points a night.

Wouldn’t you stay free free nights near the happiest place on earth for less than $100?

We both stayed at the local Radisson and Country Inn for this round. We didn’t pay anymore than $70 a night for a room this time. So between us we stayed four nights, spent no more than $280 and got 188,000 points.

We got an easy 288,000 points in six months.

Getting three nights in San Francisco cost us 132,000 points. We still have points left over waiting for our next trip.

Everyone’s hoping they’ll do it again this year, and I’m betting they will.

Mistake Fares

You can also take advantage of mistake fares. That’s when a published fare online is clearly wrong. Sometimes the airline will honor it and sometimes they won’t. This goes for hotels too.

For example there was a fare from New York City to Istanbul, Turkey not too long ago. Roundtrip was less than $400 for a $1,600 ticket. It was available for only three hours and about 5,000 people took advantage of it.

The airline realized the fare and did make a statement honoring that deal. A great deal to go to Turkey!

That’s just one example. Mistake fares are getting harder to find, but they occur occasionally.

That’s another way to get in on the fun of cheap travel.

Where to Sign Up for These Credit Cards?

Many of the travel bloggers I listed will have links to the credit cards I mentioned and more. Often an offer for a bonus is for a limited time only. Some may have a link to an offer that’s better than someone else.

Very important: The credit cards these bloggers link to are many times better than the ones if you go directly to the airline or hotel’s credit card page. So compare before you sign up. 

The credit cards companies are very strict who they accept to their affiliate program (I know cause I tried) so all I can say is to look around for the best offer before signing up.

Also don’t worry too much about taking a hit with your credit score.

I’ve applied for all these cards and my credit score is still very strong, the last time I checked.

Get Started Today

I hope I’ve proved that traveling for cheap is possible!

When I tweeted about booking this ticket, so many people asked me how I did it. I knew I had to write a post to share how I did it. That also tells me there are still a lot of people that don’t know how to get started.

It might seem intimidating but if you want to travel more for less, travel hacking could be your new favorite hobby.

Join the Travel Hacking Cartel for one buck and try it out. Read those blogs and forums I mentioned, and get in on the fun.


Finally, I want to hear from you. If you could travel first class anywhere in the world, where would you go?

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  • What an extremely informative post. Thank you for all the information. I signed up for the Travel Hacking Cartel 🙂 I can’t wait to learn more with your help.

    • Thanks Linda! I do hope that it does help other get an idea of how to get started.

  • Hey Benny!

    Long time no speak dude! Hope all is well 🙂

    Interesting and informative post. To be honest I don’t know too much about this but will definitely be looking into it more, who doesn’t love travelling! Thanks for the valuable tips and links.

    • Hey Robert! Great to hear from you! Thanks for reading. However, I don’t know how credit card bonuses are where you live. From what I understand, other countries don’t have huge sign up bonuses like the United States. However I know there are still ways, besides using cc, to get in on the fun.

  • I’m launching a blog dedicated to teaching these “travel hacking” tips to newcomers. It should be up this weekend. This summer I booked a trip for my family entirely on points/miles and I plan to do it again next year. I obtained elite status with 3 different hotel chains before staying with them, and recently secured myself 9 nights at 5-star hotels in Paris or Istanbul for $80/night! I’d love to teach you to do the same.

    PS. Thanks Benny, for patiently reading all my emails and offering such great advice on choosing a domain name.

    • I look forward to reading your stuff Ariana! I’m always learning how to be better at this. Happy to help BTW and glad you decided on a name!

  • @ Robert, Benny’s right, bonus offers aren’t that lucrative outside the US (example:, but you can always try asking them to match the bonus before you apply.

  • Aaron Andrews

    Great post Benny! I’m glad you wrote about this. I read a blog post last year some time on Travel Hacking and it sparked my interest but I never followed up, then I found this post in my Google Reader & I had to read. The post was very thorough and informative and I plan on doing some more research. Like yourself, I love just being in the airport knowing I’m about to fly some where and experience something new. I just got back from Jamaica a couple weeks ago and it made me realize that traveling is something I want to do for the rest of my life, so this blog entry was definitely an enjoyable one for me. Thanks again!

    • Jamaica would be a cool place to visit. I’ve never been. Definitely look more into travel hacking. Especially if you can sign up for credit cards. They really give away so much just for signing up. Since you love to travel, it would be perfect for you!

  • Pingback: Monthly Progress Report: Secret Project Edition | Careful Cents()

  • LOL Benny, that suite was sweet you miles hoarder you. I love miles. All my cards have been collecting miles since I can remember. I’m almost at the million mile mark on American. I’m short 200K. Not sure if i’m going to make it anytime soon. We get charged horrible fees for using our American Cards while in Europe so we use case….

    This post was so incredibly detailed.Going to make sure to pass it on to my friends..

    • I’m glad I was hoarding miles!! You almost have a million miles to spend or have accumulated almost a million since you started? Fees overseas suck, but can you apply for a card now even though you’re living overseas? The Chase cards I mentioned have no foreign transaction fee.

      Glad you like the post! I hope it was helpful and gets people started on this.

  • omg! that “suite on a plane” looks nuts! Makes any other first class look pretty bare!
    That is some serious travel hacking!
    We earn miles/points on our purchases and are members of the various airline alliances and generally manage to use the miles to get one of our tickets free when we travel and makes those far-away destinations so much more doable but nothing to the extent you are describing! We also don’t have these lucrative sign up bonuses and mattress runs here in Canada (not that I’ve seen) so good for you for taking advantage cause I’m sure a lot of people don’t!!
    Looking forward to reading the follow-up vacation summary post 🙂 ps. I love that airport excitement feeling and this post has me itching to go somewhere. Going to go check on the miles right now 😛

    • I do wonder why credit card bonuses aren’t as lucrative in other countries, especially Canada. I definitely couldn’t have done this without those bonuses. Glad to hear you do what you can with what you have! I’ll definitely have a summary post and lots of pictures next year. 🙂

  • @ VMiller, I recently launched a site especially for beginners, where I outline the 25 Steps to Mastering Miles. It’s free and teaches you all you need to know about points, miles, and free travel.

  • First, great blog.

    I wish I could have booked that Singapore first class. You got so lucky with that suite upgrade.

    I got started in the miles/points game awhile ago and I love it. I have flown to Argentina multiple times and got my girlfriend on AA flagship first class too. Miles and points are connect the dream and reality to booking your travel aspiration.

    • Hey Zach, I’m definitely lucky with that suite upgrade. I would have been happy just flying first in the 777 and experiencing business class on the A380. But I’ll take it. 🙂

  • Wow…this is totally awesome. And, I had no idea that A380’s even existed!

    I had to do a double take to make sure that picture was actually something from an airplane! Wow!!!!

    This is a great article. My wife and I do something like this (though not nearly on the same level as you) with our Westin / Amex Card.

    We use the points and rewards to book nice hotel rooms in New York City about once a year. The rooms are so crazy expensive, and we end up getting them for 60 bucks or so and some points. The Amex card has a yearly fee attached, but it’s worth it considering how much those rooms go for.

    Glad I found your blog, and great job on the iphone apps!

    • Thanks! The A380’s are beautiful. In first class on Emirates airlines, they even have a shower! Now that’s something I’d love to try. That’s awesome you and your wife take advantage of the points and rewards. I feel like if someone has good credit and can pay their bill in full every month, why not do this especially if you love to travel.

      Not everyone needs to book first class tickets like I did, but family vacations can be had for free or just paying a little.

  • Gustavo

    Definately worth the 5/6 hours searching eh! You’ve inspired me, I signed up for the Travel Hacking Cartel…cheers mate!

  • Lee

    Hi this is an amazing post. I had never heard of this. I see in one comment though this isnt very effective outside USA. I am in the uk do you know how well it works over here???? I will definatly have to find out.

    Thanks lee

  • Awesome breakdown Benny! Thanks for sharing

  • That’s awesome. I’d better to make a guide for booking the tickets. Very solid.

  • Don’t forget to ping me next time you are in SF so we can go eat some lu rou fan!

    • Will do! Lu rou fan sounds really good! I could eat that everyday for sure.

  • Suzanne

    What an exciting post. I could picture myself sleeping in the A380 in luxury and staying at a Hyatt in Sydney. I’ve signed up for travel credit cards before, but what you’ve been able to do is just fabulous. It gives me ideas 🙂

    • There’s a lot you can do w/ all those sign up bonuses. 🙂 Thanks for reading!

  • This is epic stuff Benny. I had no idea all that could be done, even though I’ve heard of the ticket/travel hacking thing for a while. Love how you broke everything down, was really clear. It’s great when people work the system, maverick style. 🙂

    • Thanks! Just wanted to let people know about this great opportunity to get free travel!

  • Hey Benny! this completely took me by surprise when I read it, I always thought that travel hacking in such a way was only possible if you had the right amount of money and connections to begin with. Looks like you’ve gotten yours off to a great start. Feeling really happy for you.

    Seems like those cards you’re referring to only apply to the United States, sadly. Someday, somehow, I’ll find a way!

    • Hey Daniel! It’s great to hear from you! Yeah it is too bad these great offers are only in the US. Wow you’re in Sweden now? That’s so awesome. But I see that you’ve started a travel blog now. Looks great!

  • Asst Exe Engineer

    Very nice information.Thank you for sharing.

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