Travel Hacking: How I Get Free Flights & Hotels

Yes, I travel a LOT for work, but one of the reasons I’m able to go as often as I do (and stay in such nice places) is because I take full advantage of the points and miles game through credit cards.

Some people call it “travel hacking,” but basically…it’s using credit card points & mile systems to cover travel experiences, usually in a more luxurious way than you would normally if you were paying cash.

I’m certainly no expert in this industry, and I’m sure there are people who do this WAY better than me (and on a bigger scale), but I do travel a lot and I’ve saved a LOT of money using points and miles. So I’m going to tell you how I do it ; )

Using Credit Card Points to Travel

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First of all, a BIG Disclaimer: You should NEVER go into credit card debt to do this. And you should never use this to justify spending more money on things than you normally would because you’ll “get points.”

Also, let’s be clear. Stringing together free stays and amazing deals isn’t as simple as applying for one credit card and getting a free trip. It usually involves a little more strategy and synchronization (and sometimes just time to accrue points).

But here’s how to start:

Pick an Airline

Southwest is my airline of choice (free bags, great sales, flexible modification and cancellation policies, plus they’re great about managing layovers), and they’ve also got BY FAR the easiest credit card point system to use.

I have this Southwest Premier Rapid Rewards Visa card through Chase. The current sign up offer is 50,000 points. Depending on where you live and where you’re going, that could be 2-3 FREE tickets.

The card also gives you:

2 Early Bird Check-Ins per year (super nice when you’re going to Hawaii and the perfect seat is really important)

6000 anniversary points

3x points on Southwest purchases (more points for your next flight)

If you’re new to the “travel hacking” game, I think this is a REALLY good place to start. You’ll get some free flights right away and honestly, I feel like Southwest points rack up sooooo fast when you’re using the card for your everyday purchases.

Again, use >>this link<< to get 50K bonus points when you sign up.

Pick a Hotel

Hotels and resorts are my FAVORITE thing to use credit card points on because there’s such a spectrum of what you could save. Flights cost what they cost, but using points on a luxury hotel could save you up to $1500 PER NIGHT.

My go to is Marriott. They have by far the most options available of any of the major hotel chains plus they’ve got a ton of luxury and boutique options (which are my favorite).

This Marriott Bonvoy Boundless card through Chase is probably my most used credit card.

As soon as you sign up for this card (and meet the minimum spend requirement) you get 3 FREE nights to use anywhere you want! The free nights attached to this card are good for hotels worth up to 50K points per night (plus you can add 15K points to each of those certificates) meaning you can book three nights at a hotel that’s valued at up to 65K points per night. There are quite a few hotels in Hawaii that will fall into that category (even more if you go during shoulder season – spring or fall).

Again, use >>this link<< to get 3 FREE nights when you sign up for this card.

But I have a “go big or go home” philosophy when it comes to travel, so I like to DOUBLE DIP on Marriott Bonvoy rewards with the Marriott Bonvoy Business Amex.

If you’re self-employed, a freelancer or contractor, a gig economy worker, if you own rental properties, etc…you qualify for a business card. (And you don’t need to be registered as an LLC or corporation. You can apply as a sole proprietorship with just your social security number.)

This card comes with three free 50K nights (the same as my Marriott Bonvoy Boundless through Chase) so right out of the gate, that’s SIX FREE NIGHTS.

Plus having both really gives you a jump on hitting an “elite status level” where you get perks like free breakfast, room upgrades, late check out, etc.

Marriott has incredible hotels (and just such a large selection) all over the world, but in the last few years, some of my favorites that I’ve stayed at with points have been:

Swan Reserve (Walt Disney World)

Ritz Carlton Kapalua (Maui)

Mauna Kea Beach Hotel (Hawaii)

Hotel Drover (Fort Worth, TX)

Liberty (Boston, MA)

New York EDITION (NYC)

The Vinoy (St Pete, FL)

JW Marriott Marco Island, FL

And the soon to open St Regis Longboat Key (FL) is at the top of my list for a points splurge!!

Hilton

Yes, yes, yes, I’m pretty loyal to Marriott. BUT I’m starting to dabble a little bit with Hilton.

They got my interest when they added AutoCamp and Graduate Hotels to their portfolio earlier this year.

I’ll also probably start checking out some of the Curio by Hilton hotels (a collection of independent boutique hotels similar to Marriott’s Autograph Collection).

Right now, the sign up bonus on this Hilton Honors (Amex) is 155K which would get you about two nights at an AutoCamp (the one near Zion National Park is SPECTACULAR).

But one of the Hilton loyalty program’s stand out features (to me) is that members can transfer points to one another without a limit (Marriott caps the number of points you can transfer to someone at 100K per year).

  1. If your travel partner (husband, wife, daughter, friend, etc) also signs up for the card and gets the bonus, one of you can transfer your points to the other and you’ll have enough points for quite a few nights.

Again, use >>this link<< to get your 155K point sign up bonus when you sign up for this card.

United

Like I said before, I always fly Southwest whenever possible, but there are two reasons why I usually will fly United:

  1. Flying into small airports for National Park trips. United has a pretty wide network and you can usually get flights into small, remote airports like Kalispell, Montana (for Glacier National Park), Eureka, California (for Redwoods National Park), Moab, Utah (for Arches and Canyonlands), Jackson, Wyoming (for Grand Tetons and Yellowstone), etc. Flying United into these tiny airports usually saves 3-6 hours of drive time from the closest major airport plus using points saves a LOT of $$$ because it’s usually pretty expensive to fly into these airports.
  2. For long haul international flights (8+ hours), you can use your United miles to upgrade your economy ticket to first class. I think that’s a great use of points and for me, it makes some destinations a lot more doable.

If you use >>this link<< to sign up for the United Explorer MileagePlus (Chase), you’ll get a 50K point bonus which could be enough to book a free economy ticket to just about anywhere OR upgrade your economy ticket to first class.

Grab that United 50K bonus here.