Travel Hacking Success Stories

Since a thread doesn’t exist yet about travel hacking, I thought I’d create one to kick start the conversation.

I started out 10 years ago only opening credit cards that would give me cash back signup bonuses and rewards. Even cards that earned miles rewards points which could be redeemed for travel, I’d only open them if I could redeem them for cash. It wasn’t until about 3 years ago that I started trying out the travel rewards points and in that time I’ve never looked back. I still value cash-back redemptions, but there was a whole world out there I was missing.

Since then, I’ve been able to take two or three vacations per year with my family with free or highly discounted airfare and hotel stays. As just about any travel hacker would contest, I wish I had started sooner! Credit issuers are cracking down on travel hacking by reducing rewards valuations and making it much more restrictive to apply for or churn the best travel rewards cards.

To get started or to stay updated in the game, there are many popular places to follow. I like to sign up to mailing lists to get daily updated info so I am aware of the many deals and changes to the cards and travel programs.

Edit to remove external links per request.

Post your travel hacking success stories here, or open a new thread for specific discussions on strategies or deals.


I’ll start the thread by posting my most recent successes. I’m winding up my two year Southwest Airlines Companion Pass, which has been extremely valuable! I was able to open 5 SW cards between me and the wife early last year and we have tried to make the most of it. Traveling to Vegas, two trips to the midwest to visit my family, Disneyland earlier this year, and will be staying 4 nights at the all-inclusive Hyatt Zilara in Cancun towards the end of this year for our 10 year anniversary, thanks to opening two Hyatt cards that gives us two free nights each. Hyatt recently changed their terms for this card to points rather than nightly award stays but I think we may keep the cards open for the annual award night (grandfathered in).

We still have a ton of points with Delta, Southwest, and British Airways (for methods of booking through the AA travel partner for cheap flights to Hawaii, which we’ll probably do next year). We’re also planning a second trip to Vegas in 2018. Starwood cards have also been very generous to us and can be transferred to Marriot to expand the hotel options.

Newbie question here. I have done the open for benefits deal for years (best coup: Chase Sapphire 100,000 points after first purchase several years back) but I have no idea how to go about getting multiple of the same card. I tried once and was rejected because “our records show you already have this card”.

Are you doing something special to get the up to 5 card deal with Chase/Amex?

Most all of the cards out there have the ability to open the same card more than once, however, each issuer has specific rules about when you can be eligible again for the signup bonuses (usually one to two years wait time, or seven in the case of AMEX). To get the 5 card deal for SW I mentioned earlier, I opened different product lines of the cards. For example:

Chase SW Plus (for me)
Chase SW Premier (for me)
Chase SW Business Premier (for me)
Chase SW Plus (for wife)
Chase SW Premier (for wife)

This allowed us to get over 250,000 SW points between us (each card offered 50k signup bonus). This was also when Chase SW co-branded cards were not included in the more recent 5/24 Chase rules.

To really get into travel hacking, there is a TON of stuff to learn if you want to be a pro (I really wouldn’t consider myself close to being a pro). The best advice is to read, read, read. Then open up a few accounts with the popular travel partners where your points will get transferred to. Before you even open your first card, develop a startup strategy for the best cards to open, such as the Chase 5/24 cards if you’re eligible because they are some of the most lucrative cards and will not be eligible after opening your 4th card in 24 months. Plan a trip you’d like to take and research how many points you need to get there and start with a small goal to see how easy it really is to make it happen. Unfortunately, I had been holding off for years to get into the game because it was intimidating to start but once you get your feet wet, it really isn’t as difficult as it might seem. Before I would get excited when I opened up a card to get $400 to $500 cash back (I still do!) but more recently I’ve opened a few cards that produce $1,000 in travel rewards with just a single card!

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Reddit churning forum and Doctor of Credit are also great stops. The issue I didn’t like with MMS was the circles and arrows approach, pimping out credit cards, and selling out his members in the HIGC fiasco a few years back. TPG is basically a Bankrate subsidiary pimping out credit cards.

Points need to be used to be valuable. I am hedging on going for the Chase Ink Business Preferred because I already have 400k UR points and have a Chase Ink Plus already, which I use to hit the occasional OD/Staples VGC under face value deals. And it’s not like I haven’t been traveling either. Maybe I will start using my Chase points as cash for travel instead, especially for hotels that aren’t chains or which I don’t care about earning points on.

A valuable tool to use points on hotels is Hotel Hustle, because it will tell you the cash and points price of a hotel and show you which are the good deals. I used IHG points on an eclipse trip and for seeing my college football team. Hotel points seem to be more useful to me than airline points especially since most of my trips are within a day’s drive or two hour flight.


Some thoughts on travel. I’m posting for the thread so pardon me if I’m preaching to the choir. I know it’s mostly skilled travel hackers here :slight_smile:

Ability to manufacture spend along with a flexible schedule from being retired or working remote is pretty much the holy grail for traveling. Amass tons of points in every program and alliance and you typically have lots of options, especially short-notice and on low load days like Tue/Wes/Sat. Couple that with the Southwest cp on deep sale fares you’re frequently traveling for bus fare or less.

Aa a list of dont’s, it’s pretty much the opposite…

Pay up to travel on Fri/Sun/holidays, especially school holidays.
Travel to Europe in the summer. Caribbean in winter, etc.
Last-minute travel for revenue-based programs like Southwest or JetBlue, with the exception of maybe using bank points for the odd last minute cheap fare.

All this is from the perspective of wanting a stupidly big balance of miles (think George Clooney in Up in the Air) and being able to go anywhere I want, pretty much whenever. If you’re a vacation once a year guy or tied down with a family- I’d try to earn/redeem optimally but wouldn’t sweat every detail. At some point- you’re better off putting your energy into earning $$$ and just buying the travel.

As for elite status- I suggest getting off that treadmill unless you’re already close from reimbursed work travel. That said- it’s valuable to have in many situations like top-tier at hotels, some of which can be earned entirely from credit card spend.

Any tricks or tips on getting free/cheap rental cars? I have no problems with airfare or hotel points but the programs for cars is really crap. I rented a car everyweek for work for a few years and wound up with something like 4 free car days after around $50k of spend on rental cars.

Whereas flying for work every week for a few years I wound up with around 30 free flights and 60 free hotel stays.

On the “transfer points” side, it seems like the few transfer rates I’ve seen have been pretty bad.

The only requirement I will add is that I must use a rental car program like Avis or National that allows walking up to the car at the airport. I refuse to stand in line for 30+ minutes at the counter and fill out a 50-page agreement form each time I rent a car.

The last few vacation trips I’ve taken have been free hotel, free airfare and either I’ve had to pay for the car out-of-pocket, or I visited places like NYC where no rental car is needed or desired. I’d probably take more fun trips if I could get free rental cars.

The $20 for $40 discover card certs for National are pretty good for a single day or weekend rental. But you can’t use multiple certs anymore.

Also, not to be pedantic, but it’s somewhat incorrect to ever regards miles/points as free. They do have a market value, even if your basis in them was zero or cheap. I always keep that in mind when I’m considering a redemption.

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Sign up for preferred status with all the car rental companies. Each one calls theirs something else…bluechip, inner circle, preferred…blah blah.

Go to autoslash for car rentals. They keep rebooking your rental and dropping the price. It isn’t as smooth as it once was but it saves me tons.

Put your number in before you book and it’ll let you skip the line when you arrive for your car.

So many stories of dirt cheap car rentals in my years of adventures.

And again MSY is right, no free lunches. Pay for the rental using cash or cash out some points but that’s not free, just someone else paying for it.

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Probably not quite what you guys are looking for, but here’s a “travel hacking” adventure circa 2001/2002, back when I was in college:

Around this time online gambling was a bit of a gray area, there were plenty of off-shore operators running online casinos, and the govt. hadn’t gotten around to using the war on drugs/terror as an excuse to clamp down on financial transactions yet. As a result the MGM Casino group was trying to grow their brand in the online space by letting players play with imaginary money (seeing as it how online gaming wasn’t exactly legal either), but win real prizes.

They offered slot machines, among other games, but since it was imaginary money the payout on these machines was rather generous so you could play for quite a while and I want to say there was an option to get more credits if you ran out. With a little playing around I figured out how to use a MACRO to click various screen positions repeatedly such that it would play the slot machine unattended by clicking in the right place to spin the reels, clear any messages that came up, and deal with any other situations that would stop the user from playing.

Once I got those details worked out I’d leave my computer playing the slot machine all night while I slept. After a month of doing this I’d earned enough MGM points to redeem for two nights at NYNY, two nights at Bellagio, numerous buffet passes (which included the VIP line so no wait was required), several show tickets (The FX Live show with Rick Springfield was one and I forget the others), tickets for the rollercoaster at NYNY, and I’m sure a couple other things that escape me at the moment. I still had to cover the cost of transportation to Vegas and back, but otherwise it was quite the inexpensive 4-night vacation.

Sadly, when it became clear that the US govt was not going to green-light online casinos and was instead taking an active role in trying to shut down their ability to get money from US players MGM pulled the plug on their site. I’ve heard they now offer some sort of Facebook games or similar to their player club members to earn points, but I can’t say I’ve even bothered to check out how they work.


One other thing. With bank points being popular and easy to acquire- always look at paid fares rather than just booking an award, if you can take the change limitations. Especially for discount business or first class. It can sometimes be much cheaper than an award and earns points on its own. For instance, I recently did a $2000 biz ticket US-Asia on QR (Qatar.) It was 100k Amex points and earned ~30k Avios and BA Silver, for a net of 70k points, An award to South Asia would have been 140k or more airline points,

Granted the Amex redemption at .02 is on its way out, but there are other decent programs.

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I’d rather hear about failures than successes. Can learn from those. Like the 75k points I have ‘stuck’ in Singapore after I cancelled some Hawaii Flights. And now Paid fares are so cheap and awards so stingy I’m watching the expiration and kicking myself.

Right there with you. The hard expiry policy of SQ and LH totally sucks. Although I did recently get forced to spend 25k sq on a last-minute BKK-SIN ticket when my husband left his medicine at the hotel and had to miss the original flight and CX/BA refused to accommodate us.

Push comes to shove, give up on redeeming for SQ Suites and just redeem for UA domestic. It’s better in almost every respect other than the fact that you have to call.

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I never consider using SQ for SQ suites, I’m cheap with my points. :smiley:

Another one: Booked a ticket with SW points to visit my spouse airside, forgot to cancel the ticket. Oof!

Or that time I forgot to account for the date change and had a hotel lined up for our arrival on the wrong day. LoL

I’ve also found that people are much more likely to give you a refund when you tell them you made a huge mistake because you’re an idiot, than when you try to tell them to give you a refund or you’ll call them an idiot.


AFAIK, they don’t enforce the no show equals void thing on rapid rewards tickets, but you have to call to get it back. Give it a shot!


Yep, I was able to get it back by calling. That’s when I started to learn that you really can do almost anything with the right phone rep. HUCA for life.

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I’m a huge fan of SW, not just because they are one of the cheaper and better bang for your buck airlines but because they have a fairly good customer service base and it is so easy to cancel/refund flights with no fees. On a couple of occasions I’ve checked and found discounted deals on flights that I had booked 5+ months in advance. It was easy to call the rep and refund my points for the cheaper fare (usually you can just cancel and re-book online but I had a companion attached so had to call the rep to re-book).

I agree you have to take the blogger sites with a fair understanding that they are trying to monetize their business and will often push products harder when they affiliate link payouts. I appreciate getting daily emails to keep me updated on some of the latest deals and strategies without having to go searching for them though, and often find key bits of timely info that I can jump on or sock away for later use.

Absolutely, points have value attached. When I mentioned “free” in my earlier post, I suppose it was more in reference to the all-inclusive resort but the term “discounted” is much more on-point when talking about travel points and redemption. Acquiring points is by no means free, as it requires time and cost to open/close the cards, MS for the signup bonus, etc. Some of the better cards also have annual fees (not waived) that assign a real cost to getting the benefit, or the opportunity cost of spending on a traveler card vs a CB card. There is also the aspect of scarcity since there are limitations to qualify for the cards or the signup bonus.

One of the first things I did when evaluating which travel cards to apply for was create a comparison spreadsheet where I could assign a value to points in different programs. That has been very helpful to this day as not all rewards points are created equal across different programs, or priced the same for tickets or reservations.

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Agree. I tend to keep some idea of the valuation in mind just so I don’t just blow them on random trips because they’re free. Like a day trip to DCA just to go to a museum or something. Those 15k Avios are worth ~$150, so would I really spend $150 on the trip?