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  • Writer's pictureJake

Come Fly With Me, For Free

In my opinion, you aren’t really living your best life if you never get out there and see the amazing places, people and cultures that exist beyond your own 4 walls. As John Lennon put it, “Living is easy with eyes closed." So we can agree that we want to get out there and see it all but on the tight budget of a 20-something, it's all too often easier said than done right? Well, kind of but not really. You just have to know how to play the game… kind of like dating I suppose. So I’ve learned a few tricks that have won me FREE flights and hotel rooms so that I can galavant about the country and the world pretending that I know more than I actually do. So how can you fly like me, for free?

It's all about those points! Some programs call them miles but its all the same thing and I will use the terms "miles" and "points" interchangeably here. The key is to maximize the amount of points you earn while spending the least amount of money to get them. I want to share 3 tricks that I have used to do this and the 3 things you’ll need in order to take advantage of these hacks. You need:

What is it? Only the greatest travel app out there. You type in the dates that you are looking to travel and it does 2 things. It gives you the lowest possible price available if you book now and it tells you if you will get a better price if you wait to book. It even alerts you when that time comes!

2. Rewards Membership With All Major Airlines

What is it? Its free and you’re stupid if you don’t have one with each airline because you are opting out of receiving credit toward free flights by not being signed up. All airlines have them although some have different rules as to the expiration of points and for what they can be used for. In general though, they work as points that add up to free air travel on that specific airline or with their alliance partners. I've included links to sign up for each reward program at the end of this post so be sure to sign up!

3. Travel Credit Card- Independent from an Airline

What is it? A credit card, not tied to a specific airline that rewards you with points toward travel for every dollar you spend and usually more points for money spent on travel itself. I recommend the Chase Sapphire Preferred Card. It has a $95 annual fee that is waived for the first year as well as a huge 50,000 point bonus for spending $4,000 in the first 3 months. You can sign up for it here. I have this card and the Capital One Venture Card that has no annual fee but does not yield as many travel points per dollar spent. More on how these bonuses and points later.

Before continuing,

I do want to be completely transparent with you here. I just signed up for the Chase Sapphire Preferred Card to get my bonus points so I really do recommend it. If you follow the link provided here to sign up for the Chase Sapphire card, I will receive travel points for referring you. So if you want to take advantage of the tricks I am about to show you and help me out in return, I’d appreciate-cha! This is something that you can take advantage of too if you sign up and is another great way to get free points!

Okay, now let’s fly! You have the app, the rewards member status with the airlines, and the card. Now you need to decide where you want to go and when. Use hopper to shop around for cheap places and times to fly out of your closest airport. In general, the more flexible your days and times are the better but there are always ways to make it work. If you already have some points to spend on the flight, remember that cheap prices mean less points so cheaper is always better no matter how you’re paying. I suggest checking flights to Denver, Chicago, Orlando and New York to test things out because they are always the cheapest due to the airline's hubs in those cities as well as the frequency of flights through them. Plus, they’re all great places to visit! Now, let’s look at the 3 tricks I promised!

[Que: Let’s Fly Away - Frank Sinatra]

Spending The Least For The Best Deal

Maybe you have to go to a wedding or you’ve got some spare change and you want to take a trip to say, Chicago. Chicago has 2 airports and 2 major airlines that fly through each of them. Let’s say that you want to fly in on a Friday and leave on a Monday morning. United Airlines is headquartered in Chi-town and they send over 500 flights through O'Hare per day. Using Hopper, you know that United is offering a cheap deal into Chicago on Friday evening which is perfect, but guess what? They bumped the price up for Sunday and Monday for your ride back home! Oh no! But don’t fret. Let’s say that Southwest, for example, offers a cheap flight from Midway airport (just as nice as O’Hare) back home on Monday morning for a great low price. If you booked through a booking agency or the airline, they would have coupled you onto one airline, but because you are smart, you know that it can be cheaper to book 2 one-ways and you’ll earn some great points with BOTH airlines rather than one. This also gives you the option to pay for one way with points and the other way with dollars. Book the flight in with United and out with Southwest using your new travel card. You will earn 2 points per dollar spent with the Chase Sapphire card and it actually has 25% higher redemption value than the points of other travel credit cards. Because you signed up for Southwest’s Rapid Rewards Program and United’s MileagePlus Program, you also earn miles for the flights with each of the airlines. This is the fastest way to earn points toward free flights without really doing anything extra. In no time, you will have built up a nice bank of points that you can redeem for free flights between what you have with each airline and with your credit card.

Credit Card Points- The Ultimate Cheat Code

Millennials have loved cheat codes ever since Mario taught us that there’s always a secret tube no one knows about that will take you to Bowser’s Castle. Fortunately, there is a small cheat code with air travel points too. Suppose you want to take a big trip in the near future and you don’t want to pay for it. The fastest and most controversial way to earn a lot of travel credit in a short amount of time for relatively no money is to sign up for a travel card, like the Chase Sapphire Preferred Card or the Capital One Venture Card. When you sign up for these cards and are approved, they will offer you something like 20,000 free points or 50,000 free points, depending on the card, for spending some amount of money across the first few months. Assuming that mommy and daddy don’t pay for everything in your life anymore, you have certain expenses per month like groceries, rent, insurance, eating out, going out, gas, and clothes that you have been putting on your debit card. Have you ever added up what you spend each month on all that? It’s more than you think and if you’re spending it anyway from your checking account, you're wasting it. Why not put it on a credit card that rewards you for doing so. Just be sure not to spend outside your means and pay it off each month. As long as you’re responsible, you can’t do anything wrong; a statement that is perhaps applicable to many other areas of life, but we can discuss that later. After a few months, you will be rewarded not only with the points that you earned per dollar spent but with a huge bonus of up to 50,000 points, depending on which credit card you chose. In other words, for just spending what you normally do, you get at least 1 free flight and then some. After you spend the bonus points on your trip, you can choose to keep the card open and keep earning points or you can close it with no penalty. Just keep in mind that closing credit cards will usually affect your credit score.

Maximizing Your Points

There is one final trick I have learned that will allow you to maximize your points on your card and with the airlines. This one works if you can afford to plan ahead a bit. Again, you will be taking advantage of airline reward programs and a travel credit card. Southwest does something really fantastic where they actually sell rewards points that you can buy toward future flights. Other airlines do it too but it seems like Southwest has better deals. Like anything else, these reward points go on sale! They really do think of everything there! So if you are going to be traveling in the future, you can hedge the market and buy your reward points at a cheaper price while they're on sale than if you just earned what you would from traveling with that airline. Southwest will offer different packages with something like 50% more points for an extra $30. Remember to buy these with your travel card so that you are getting the cheap points from the airline and earning points with your credit card at the same time. Taking advantage of this can get you something like 10,000 points for $200. That right there is a free flight when you would have normally had to spend something like $400 on a flight to get that many points. You can watch for these sales by signing up for the airline's marketing emails where they will routinely announce these deals.

So there you have it, points, credit cards and apps… Welcome to the 21st century! I have talked to people before about the American misconception that travel isn’t affordable. It definitely is! You just need to be smart, a little flexible and open to accommodations that aren’t always in a resort, a deeper lesson for us Americans in general perhaps. When choosing a place to go, reach out to friends or acquaintances who live there and see if you can stay with them. Also, be open to hosting others who want to come visit you! Afterall, friendships are a 2-way street. When there’s no one whom you know available, check out Airbnb and for god’s sake don’t be afraid to stay at someone’s apartment while they live there! I promise that your Airbnb host is not going to click their heel and make a knife pop out of their shoe to attack you before you leave (This is literally what my dad and uncle thought…too many James Bond movies).

A few readers had asked me to write this after they learned that I was traveling for free to Denver this weekend to go skiing. I earned that free trip and I am planning at least one big trip to Europe and Istanbul this year using the cheats I explained in this post so I wanted to share with you what I have learned. Please share it with your friends and family and tell me about the places that you go and how you did it! I know that there are probably more cool ways to travel for cheap or for free so if you have any comments, suggestions or feedback I would love to hear it. Keep those eyes open to all the places out there that have yet to be explored. Travel more and pay less!

Airline Free Reward Program Links:

Travel Reward Credit Cards:

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