8 Simple Ways to Fly for Free
Yes, you read that correctly: FREE.
In 2016, our first big year of family travel, our little family flew for an entire year for little more than $100.
How did we do it? To be honest, there is no one simple answer.
In most ways, we lucked out big time taking advantage of Matt’s work travel schedule. But that only got us so far. To fill out the rest of our travels, we had to use different methods of “travel hacking”.
Now, I’m not a “travel hacking” expert by any means, but it’s something I hope to learn more about as our travel continue. Travel hacking is essential “gaming the system” to earn free travel through points and rewards programs. Nomadic Matt has a great list of travel hacking tactics if you have time to dive into it.
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But for now, I wanted to share a few extremely simple ways us newbie frequent travelers were able to fly for (almost) free for an entire year. Here goes:
1. Take Advantage of “Bleisure” Trips
This was the biggest opportunity for us, and understandably not an option for everyone. But if you or your spouse has a job that requires any sort of travel, combining business with leisure trips is a great way to get your flights paid for you. Bleisure trips are becoming more and more acceptable by employers, and I recently read a statistic that a whopping 62% of millenials have extended a business trip for personal travel in the last year. So if you’re scared about making the proposition to your boss, don’t be. This is likely not the first time they’ve heard (or granted) the request.
It’s no surprise that most of our travels in the past year involved flying to the Bay Area since that’s where Matt’s working at the moment. To make the most of his frequent travel, we started a Bay Area bucket list, and planned several trips that extended over a weekend or two (Monterey, Santa Cruz, & Napa Valley, to name a few). We used the weekends to explore all the area has to offer, while Matt worked during the week. And since Evelyn is still under two, she flew on my lap for free.
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2. Use Airline Frequent Flyer Miles
While it’s a good idea to sign up for a frequent flyer program for any new airline you use (it’s free!), it’s still best to stick to one or two airlines (preferably which operate in an alliance) that cover your most frequent or desired routes.
For us that has meant flying Southwest nearly exclusively, with the occasional Delta and United flight sprinkled in (depending on routes, costs, etc.) We particularly love Southwest because they fly nearly everywhere in the country, have super flexible change policies, free checked baggage (hello, tons of baby stuff), and (best of all) the best frequent flyer program out there of all the US domestic airlines.
Points are easy to accumulate with Southwest and they have flexible valuation (whereas other airlines will charge you a set amount of points for different routes no matter what the actual price of the ticket is). For example, on Southwest if you book during one of their fare sales, you can get to and from some direct destinations for as little as 5000 points each way!
We used Matt and I’s frequent flyer miles to make it to Chicago, as well as cover part of our Mexico flights. (more on that below).

3. Extend a layover
You might be surprised to learn that booking two one way flights with a stop in the middle can sometimes cost little more than one continuous route with a layover in the same city. So if you’re looking at doing a multi-city trip, it might make sense to stop for a few days rather than a few hours on your way home, and see an entirely new city while you’re there.
On one of our trips back home from California, we did this very thing: extending our layover in Salt Lake City and spending the weekend in Park City before coming home to Omaha.
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4. Sign Up for a Travel Rewards Credit Card
Trust me, I hate credit cards. I hate any sort of debt, really. But with all of the travel we wanted to do, we needed to be taking full advantage of all of the resources out there. And one of the greatest resources for saving money while traveling is a travel rewards credit card!
So early in 2016, we signed up the to Chase Sapphire Preferred credit card, which currently awards a 50,000 point sign up bonus. You receive 1 point for every dollar spent on all your usual purchases, along with an extra point for every dollar spent on travel and dining (huge for us!). It’s worth noting that Chase recently came out with the Sapphire Preserve credit card (sounds fancy, doesn’t it?), which has a bit higher yearly fee, but gives you double the sign up bonus and 3 times the points on travel and dining! If you plan on doing any sort of regular travel as a family, I’d highly recommend looking into either of them to see if they might work for you.

5. Book through Chase’s Travel Partners
When it comes to redeeming points with Chase, you can either book through their portal (which gives you an ok, but not great redemption value), or (this is my favorite part) transfer your points 1:1 to their partner airlines and hotels. This makes the points much more valuable! Currently, Chase is partnered with Southwest, United, KLM/Air France, British Airways, and a few others. So hypothetically, we could fly to Paris using Air France points without ever having taken an Air France flight in our lives!
We used this tactic to maximize our points for Cancun. We didn’t have quite enough Southwest points to cover our tickets, so we transferred a few over from Chase and voila! Free flights!
6. Sign Up for Airline Rewards Credit Cards
We haven’t signed up for many airlines rewards credit cards yet, but they can be a valuable tool as well. It’s best to stagger when you apply based on which airline you plan on using the most for your upcoming travels and then taking advantage of the sign up bonus they offer. The Points Guy is a great resource to follow for alerts on who to sign up with and when.
The one card we did sign up for in 2016 was the Southwest Rapid Rewards Credit Card because 1) we fly them so much already, it just made sense, and 2) we really wanted to earn the companion pass. (keep reading…)
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7. Fly with a Companion Pass
What’s the Southwest Companion Pass, you ask? It’s the most valuable frequent flyer perk out there, and also surprisingly not that tricky to earn. It’s awarded once you’ve accumulated 110,000 Southwest points, which seems impossible at first – you’d have to fly them atleast once a week! But, if you sign up for the Southwest Rapid Rewards Credit Card at key times, you’ll receive 50,000 bonus points towards that total. Suddenly, with all Matt’s Southwest business travel, we were within reach! We earned the companion pass just in time for our trip to Mexico, which allowed us to get Evelyn her own seat on the plane for free, flying as Matt’s companion.
We’ll have the companion pass through the end of 2017, meaning we’ll never have to purchase a flight for Evelyn (so long as we’re able to book a Southwest flight) for the entire year of 2017. Woohoo!
8. Redeem Credit Card Points for Cash
Ok, so we didn’t fly totally free in 2016. But that one’s not our fault. The thing is, even if you book with 100% points, you’re still required to pay taxes and fees on each ticket (like the September 11 Security Fee or airport taxes). Most of the time (domestically) this comes to $5.60 per person each way, but the amount can vary if you’re flying internationally or into an airport with a steep fee. When flying to Mexico we ended up paying around $70 for each ticket. Still not bad, if you ask me!
The good news is, if you want to offset those costs and fly totally for free, you can always redeem your Chase points for cash at $1 per 100 points. While we’d personally rather hold onto them for booking future travel (where they’re more valuable), it’s just one more reason to love travel hacking in it’s many forms.
Alright, you can probably tell this whole points thing gets me a little jittery and excited. I’m telling you, once you get started, it’s addicting!
Have you ever tried travel hacking? Tell me your secrets!