Earning free flights and complimentary hotel rooms doesn’t require riches or celebrity. The pursuit of this also doesn’t have to be complicated. Here’s my Travel Hacking 101 guide for those who like to travel for free but are afraid they will have to make it an obsessive hobby.
I’m currently traveling around Europe, where I’ve been for months now, and I’ve managed that through home exchanges, strategic bookings of Airbnb and Booking.com apartments, and a long-term rental for a month in Bulgaria. But I’m also flying for free sometimes and have booked hotel nights in Geneva, Sofia, and Munich that I didn’t have to pay for.
What most infrequent travelers don’t realize though is, based on at least 100 conversations about it now, is that you don’t really have to be very loyal to earn the perks. Most “loyalty” points don’t come from flying the same airline a lot or staying at the same hotel chain a lot unless you work in sales and you are using an expense account every week. Most travel hackers gain their points through strategic spending on other things besides travel.
It also isn’t all very difficult or complicated to earn gobs of points if you have a decent credit rating. It’s easiest in the USA for sure, where the whole “perks for loyalty” idea got codified originally, but if you search for travel hacking ideas where you live, you’ll probably find specific local options.
If you corner some expert on earning frequent flyer miles and loyalty points for some advice though, your eyes will probably glaze over in less than a minute. “This is harder than math class,” you might tell a friend soon after. “Too complicated for me.”
The Basic Strategy to Gain Miles for Flights and Hotel Rooms
The whole airline miles and hotel points game can seem more complicated than the table rules at a casino. Those who play it to really win at every session are super serious and strategic about it. They are like the card counters. They try to find every winning angle because they know the house usually has the edge. It’s a serious game to them and they are playing to win.
The rules are complicated and the cash-ins difficult because the owners of the game—the airlines and hotel chains—want it to be difficult. If they can get only 33% of participants to actually cash in those miles instead of, say, 38%, then that difference can potentially be a billion dollars more revenue over the course of the year.
For those who are not paying attention to their balances, maybe those miles or points eventually expired (now worthless). Or they were written off at pennies in value for the programs on the company balance sheet because they got devalued through a simple rules change or award chart reorganization. Either way, the house won.
There’s a way to do pretty well at travel hacking without spending lots of time on it though: just play basic strategy.
If you have played blackjack, the analogy will make a lot of sense. There’s a basic guide to blackjack that’s small enough to fit on one playing card. There’s a certain way to play every hand based on the cards you get. You won’t always win, but the odds are best on a certain action. On a 10 and a 9, you always stay because you’ll probably win. If the dealer has a 10 and a 6, you stay no matter what you have in your hand. If your cards add up to 10 or 11, you take another card no matter what. Depending on what the dealer has, you might double your bet too.
Follow the basic strategy, leaving emotions and hunches out of the actions, and you’ve got good odds of coming out ahead over the course of a few hours. At the very worst, you should just lose a small percentage unless you have really terrible luck with the cards you were dealt.
When it comes to travel hacking, there is also a basic strategy. If you can just remember the following key moves, you’ll be on the fast track to free flights, free hotel rooms, and even free rental cars for your next vacation.
I want everyone to be able to play this game and win. After all, “I wish I could travel more” is a lame thing to say.
Get an Airline Credit Card (or Two) to Start Travel Hacking 101
It’s better to spend than to fly when it comes to earning free flights.
As counter-intuitive as it sounds, flying a lot is a terrible way to earn frequent flyer miles. Once upon a time you earned real “miles” (or kilometers) for your flight based on how far you went. While some foreign airlines still follow that logical measure, only Alaska Airlines still does in the USA or Canada.
The rest operate on a point system based on revenue. In other words, if you pay the big bucks to fly at the last minute in business class, you will earn a lot no matter how far you fly. If you go from NYC to Singapore after snagging a great flight deal, however, you will be disappointed. I once earned less than 1,000 “miles” after flying all the way from Los Cabos to Florida. One flight from Europe to the USA on one of the big 3 legacy airlines earned me just 1,280. It’s not any better with their partners.
If you sign up for the United Airlines Chase card though, you often get a fat 30,000 to 60,000 points (or more sometimes) after you spend one to three grand in the first three months. So you’ve got enough for a free round-trip flight to Mexico or Canada just for getting the card and using it. You typically earn at least one point per dollar after that, often more if you take advantage of bonus offers. Charge your basic monthly bills and gas, then pay off the bill each month. With $500 a month, you’ve got 6,000 points just from paying bills.
You can get a similar deal with Southwest: currently 60,000 points upon sign-up and spending $3K on the card as I write this. See the details here. Southwest points are easy to cash in and use on any flight, with no complicated charts or blackout dates, so you’ve got a big advantage with them for flights within the USA and to Mexico.
Right now you can get 60,000 miles by getting the Delta American Express card and putting $3K on it within three months. After that you’ll have 63,000 miles at least. You can go a loooong way on that, plus you’ll usually get a free checked bag and faster boarding for stowing your carry-on.
With an airline credit card, you normally get rewarded extra miles for buying a ticket, eating at the right local restaurant (3X or 5X miles), or using their online shopping mall portal to go buy things online (2X to 10X). Then you usually get some kind of perk with it too, such as waived bag fees (easily worth the annual fee if you have to fly a legacy U.S. airline), priority boarding, and different kinds of buying or redeeming discounts, depending on the airline.
I fly a lot and don’t often have my choice of airline if it’s work, so I’m a bit of a freak on this category. I’ve got cards from Delta, United, American, and Southwest. The last one doesn’t charge for bags, so they’d be my first choice normally anyway if I need to check something, but this way I know I’m set no matter what. I often check a bag if going to/from a trade show or have another reason to need to dress for multiple situations, so this way I don’t have to sweat any extra charges.
Unless of course it’s not domestic but it’s not really international on American.
I have also gotten bonuses of 60K or more from American Airlines for their cards, getting me some nice long-haul flights. I have American Airlines cards from Citi and Barclays but I can’t really recommend them though if you’re only getting one. American was the worst airline to fly during the pandemic and they still rank at the bottom on most surveys and ratings years later. On top of that, some of their cards charge foreign transaction fees, they frequently find ways to deny the free bag perk (and never include international flights like United does), and their cards typically have the highest interest charges.
But through all these cards, I have flown so many free flights now I’ve lost track. I’ve been round-trip to Chile, Argentina, Peru, Belize, and Fiji on miles for starters. I’ve covered a dozen flights between the USA and Mexico this way. I think all three times I’ve flown to Argentina I’ve done it on free flights to avoid the $1,000+ they were listed for, the last time using points scored with my United Card.
Get a Hotel Credit Card to Upgrade Your Stay
As with flights, the fastest way to get free hotel stays is not really by traveling more and being loyal. It’s all about racking up points in other ways. Thankfully the big hotel chains make it easy, so this is an easy first step in Travel Hacking 101.
In many ways, a hotel-branded credit card can be more valuable than an airline card. After all, nearly everyone books more hotel nights than they do airline flights. So it’s easier to earn points and easier to cash them in. If you can only get one travel credit card right now, I’d recommend a hotel one.
My specific first choice would be the IHG Rewards Club Premier card from Chase. I’ve had an IHG Mastercard for at least a decade now and I’ll honestly say it’s the only one where I’m actually happy to pay the annual fee. That’s because on each anniversary, when you pay the annual fee you get a reward night at almost any of their properties.
There’s a points limit, but in the past few years I’ve managed to cash my free night in for hotels that were going for $300 or more per night, like in Washington, D.C. at The Willard Hotel right behind The White House (pictured below) and at the Intercontinental in Prague. I earned my fee back several times over. More recently I cashed in that annual free night for the Intercontinental Buenos Aires and soon I’ll be using that credit for a hotel of theirs right in central Munich, saving me about $180.
Besides that, you’re buying your way into Platinum Status with this card, which means you get a space-available room upgrade, a bonus amenity at check-in, and higher points earnings—including in their dining program. It’s almost impossible not to earn your fees back bigtime with this card, especially with all the promotions they’re running regularly.
Apply through this link and you can get 80,000 miles (usually) as soon as you meet the spending requirements. In my experience, that’s easily enough points for four hotel nights at a Holiday Inn Express that gives you breakfast for two.
Of course you need to pay it off each month. Otherwise the math gets much worse.
If you bank the points though, you could make out very well. Instead of staying in a hovel, you could cash in some points with Hilton if you have their credit card and stay at a Waldorf Astoria or at least an Embassy Suites. I’ve cashed in their points for free stays in so many places I’m losing count, but for starters, the list includes Sofia, Geneva, Miami, Medellin, and Orlando.
I recently upgraded to their Surpass card because it offered a huge sign-up bonus and Gold status, which has already paid off for me. When I stayed in Sofia, we ended up getting free breakfast and a dinner/bar credit because the executive lounge was under renovation. It also gives me 10 free airport lounge visits with Priority Pass.
A few years ago I also applied and got the Wyndham hotel chain credit card and I’ve been quite happy with that one too, especially when I was staying for free at this Wyndham Esplendor in Patagonia, Argentina. The sign-up bonus was quite generous and I like the fact that their award cash-in chart is refreshingly simple compared to the one at Marriott, where you have 11 or 12 tiers to navigate and upper redemption levels that can be 2 or 3 times the highest Wyndham Grand cash-in.
The other option, if you don’t or can’t have another credit card, is to use a loyalty program that goes around the regular loyalty programs. The best-known one is probably at Hotels.com, where if you stay 10 nights through them, you get an 11th night free based on the spend average. This is not really ideal though because, well, you have to book 10 hotel stays to get any benefit.
Get a Credit Card That Plays Well With Others
If you don’t like the idea of being tied to a certain brand or you just want to keep your options open, a card that offers transfers to different programs can be appealing. With these cards, you bank points that you can transfer out to those hotel and airline programs as needed, when you’re ready to take a vacation or you need to top off an existing point balance.
The best-known program is from American Express, their Membership Rewards program. It’s not the powerhouse it used to be since North American airlines are limited to Delta, Aeromexico, JetBlue, Virgin America, and Air Canada. Their hotel program transfers have gotten better lately though since they added Marriott—now the world’s largest hotel chain with 30+ brands. They also allow transfers to Hilton and Choice Hotels. Check the sign-up bonus here.
The other favored cards among frequent travelers are connected with Chase Ultimate Rewards, primarily the Chase Sapphire Preferred or Reserve. With this program, you can transfer points to United and Southwest on the airline side or use the points to book a flight on any airline with the points value in your account. Hyatt, IHG, and Marriott are all transfer partners for their points.
As with the branded credit cards, some of these carry an annual fee that can outweigh the benefits, so if you’re not traveling much it may be best to let them go after a year or two. After a while, loyalty might not pay. Plus don’t forget that you can buy your way into lounge access in most airports with Priority Pass.
Don’t get hung up on the annual fee though: paying more can often get you 3X the benefits, so a card that doesn’t get much for its $0 annual fee may pale in comparison to the one with a $95 fee that showers you with perks and freebies. Just understand what you’re getting and make sure you’ll use the benefits. Elite status or lounge access might not be worth much if you don’t travel enough to use them.
This post has been about travel credit cards because as you may have figured out by now, that’s the basic strategy. Travel Hacking 101 can be summed up quickly: get the right credit cards and use them to your advantage.
Spend wisely and double-dip or triple-dip when possible. Make sure every time you spend a dollar on a credit card, you are getting some kind of tangible benefit from it. Sometimes you can get a huge benefit. I paid my kid’s college tuition on a credit card for years. That’s more points than I’d like anyone to know, but it was a bill I had to pay regardless, so I just hit the jackpot!
If you want to step up without making things too complicated, sign up for the credit card company’s e-mail list and pay attention to promotions. You could get 5X points for just using their card at a gas station or grocery store. They all run dining programs where eating at the right restaurant can earn you extra points.
Just understand that your choice may be more limited if you live outside the marketing-savvy USA, where companies aren’t so good at understanding lifetime customer value or how points can equal money in their stock value. Check sites like this for Canada though and find alternative sources for travel hacking in other countries.
If you have bad credit though or Dave Ramsey has convinced you that credit card spending is evil because you can’t be trusted to manage your money, then just grab the cheapest deal every time and that’s your strategy. Just understand that you are potentially leaving a significant sum on the table for someone else to pick up while you play with cash in envelopes.
Disclosure: I encourage you to do your homework independently. I can get some bonus points for the referral for some of these links as an existing customer if you follow my lead, but the terms should be the same as you could find independently on your own.
This Travel Hacking 101 post was updated in June of 2023.