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Three Ways to Find Cheap Flights

We use real estate investing to fund our lifestyle and traveling by cheap flights is a big part of that for us. In this two-part Travel Hacking series, I will be sharing travel tips I use to maximize credit card rewards and minimize spending on travel. Click here to read the entire series.

In today’s post, I will share three ways to find cheap flights. “Cheap” flights aren’t for everyone and some of you will pay for conveniences like a direct flight or better flight times. I am not here to convince anyone to act otherwise.  I am sharing these three tips because the question I get asked the most is: “How do you find cheap flights?”

1. Use Google Flights and Skyscanner

There are dozens of reputable sites and search engines designed to find flights. With how much I fly, I can tell you my two favorites continue to be Google Flights and Skyscanner. Yes, I have used Kiwi, Kayak, and Expedia and those are not my favorite. Lately, I am finding my best deals using Google Flights. I thought I knew every trick in the book when it came to finding cheap flights. Tricks including but not limited to:

  • Travel on a weekday
  • Use incognito window on your internet browser
  • Shop on Tuesdays
  • Search for one-way flights as well as roundtrip
  • Check nearby airports

Then I watched this video, where Nicole at Scott’s Cheap Flights shows us a Google Flights tutorial. My mind was blown. I learned more in this eight-minute video than I thought possible considering I flew 41 times last year and booked all of my own travel.

I now use Nicole’s tricks every time I am shopping for flights. The trick using five airport codes to five airport codes is my new favorite hack! It allows me to type in five U.S. cities to five Asian cities and find the cheapest flight.

While I use Google Flights, I still religiously use Skyscanner and will continue to use their Everywhere feature.

How to use the Skyscanner Everywhere tool: Open Skyscanner and type in your departure airport. Then in the “To” box type in the word “Everywhere,” and you can click “Can’t decide where? Click here to search Everywhere.”

Click “Search flights” and Skyscanner allows you to see multiple destinations by price. This is especially fun when your trip is open-ended, you’re planning a family vacation or you have the ability to work from anywhere in the world.

2. Watch flight prices like you watch the housing market

When you’re investing in a specific real estate market, you pull comps and buying flights should be no different. I am constantly looking at flight patterns and prices. I know how much flights cost to Amsterdam in April and Medellin in May. If that sounds like too much work, let the experts help you.

Receive flight deals right to your email inbox from several travel websites. Similar to how we send real estate deals to our Addicted to ROI Insiders through our Deal List, established travel websites send you error flights and flight deals.

Subscribe to a few newsletters. Some of my favorites include:

  • FareDrop. Kara and Nate are a famous traveling duo who run their Kara + Nate YouTube channel. Their new venture is Faredrop. Sign up and you’ll receive deal alerts. They also text me the deals, which I like. The deals I receive from FareDrop are shockingly good. You can find deals like Houston to London for $387 round-trip (normally $950) or Los Angelos to New Zealand for $617 roundtrip (normally $1,250). I pay $47 annually for FareDrop.
  • Secret Flying. Secret Flting often posts Error Fares, where airlines make a mistake posting insanely cheap flights like this $277 roundtrip ticket from New York to Tel Aviv (normally $964).
cheap flights
A recent post on the Secret Flying Facebook page.

Do you see the blue star in the top right corner of the photo above? I liked the Secret Flying Facebook page and made it the first thing I see when I get on Facebook. Posts from Secret Flying are the first thing I see on my Newsfeed and more often than not, I click on a post rather than aimlessly scrolling through Facebook

Set up price alerts on Skyscanner, Google Flights, and Hopper. Hopper is a free app that will tell you to wait or purchase now. However, I do not advise that you purchase inside the Hopper app, Hopper will charge you a $5 fee. Instead, use the app to find cheap deals and then buy within the airline or Skyscanner.

Don’t be afraid to pull the trigger. As Deena is always telling new investors, “take action!” I can be heard saying, “buy the flight!”

3. Book your flight from a hub airport

If you don’t live near a large hub like Atlanta, Dallas, Houston, Chicago, Newark, DC, NYC, SF, or LA, you are likely overpaying for flights.

When I fly to Europe, I don’t look at flights from my home airport to Europe. I look at flights from JFK, Boston, Newark, and D.C. to Europe. Then I purchase a separate flight to that East Coast airport.

Note: there is a risk when buying two separate tickets. I will tell you how this cost me a few hundred and a night of sleep, but first, let me tell you why I continue to do this despite the risk.

Riding a motorcycle through Vietnam and seeing the Great Wall of China had been dreams of mine for six years and this last November, I did both.

First, I booked a roundtrip from Los Angelos to Beijing for $325 on Delta using my Delta Skymiles Gold American Express. This card earns me 2x points per $1 spent on Delta and free checked luggage.

I wasn’t living in Los Angelos at the time, I was coming from Mexico City. Instead of buying a flight from Mexico to China, I bought a cheap flight from Mexico City and then another cheap flight from Los Angelos to Beijing.

I flew from Mexico to LAX for $87 one-way and then caught the Delta flight from LAX to Beijing. If I had purchased a flight from Mexico City to Beijing, I was looking at prices of $1,200 round-trip.

Quick math: $325 + $87 = $412 is way better than $1,200. Plus, I was not going back to Mexico City after Beijing, so I did not want a roundtrip ticket. A one-way from Mexico City to Beijing was $893. Still, $412 is better.
Those are the three ways I find cheap flights. In 2019, I took off 41 times. I have been traveling for years and I, too, make mistakes. I’ll share one with you now.

Booking separate tickets is risky…

I had just finishing traveling in Ireland and Scotland with my dad. My dad can fix and build just about anything construction—just don’t let him touch your car. As a thank you for all his help on my first house hack, I took him on a ten-day trip to his bucket list destination: St Andrews, Scotland. Any avid golfers out there should add this to their short-list. Scotland is amazing! It was our first time abroad together and one of the best travel memories of my life. The journey home, however, was a near-disaster.

My flight from Dublin to Chicago was delayed for three hours because of mechanical failure and it caused me to miss my connection flight from Chicago to Denver. If I had booked this all on one ticket (Dublin to Denver) the airline would have been responsible for rebooking my flight to Denver and possibly even putting me in a hotel.

That wasn’t the case.

As I mentioned earlier, I love saving money and this time, it bites me. I had bought my flight Chicago to Dublin roundtrip for $492 on Aer Lingus and a separate ticket for $77 from Chicago to Denver on Spirit Airlines. Yes, I can see you rolling your eyes. I admit cheap airlines come with a set of problems sometimes.

I thought I gave myself ample time with a five-hour layover in Chicago and Global Entry, which allows me to breeze through immigration, which is done in the Dublin airport before you depart so immigration was not going to be an issue.

With the Aer Lingus flight five-plus hours delayed, I missed my connection. To my luck, there were zero flights later that night because it was already 10 p.m. by the time I landed in Chicago. And because I purchased the tickets separately, neither airline would take responsibility.

It is nearing 11 p.m. and I was stuck in Chicago. Plus, I needed to be in Denver, dressed and ready to attend a 10 a.m. wedding. (Yes, you read that correctly, a 10 a.m. wedding – don’t get me started). 

In a panic, I called Chase Sapphire’s customer service. A perk of having the card is a 24/7 concierge. They looked up a few flights for the very next morning and they were $300+ for a one-way flight. They’re a concierge, not a magician.

So, I got online to my favorite airline site and searched and searched, nothing was beating $330. So, in desperation, I called my friend, Susheel, who is a travel agent and happens to live in Chicago.

photos of two friends outside in the cold
Susheel Kumar and I outside O’Hare airport in October 2018. We met at a summer camp in 2006.

To my surprise, he answers. It’s 11 p.m. on a Friday and after hearing my sob story, I can hear him already clicking away at his computer. He asked me one question, “do you have a checked bag?”
“No why?” I ask.
“Okay good,” he replied. “I can get an early morning flight for $160 from Chicago to Seattle with a stopover in Denver. You only having a carryon saved you this time.”
I corrected him, “no, you saved me this time.”
I gave him my Chase Sapphire Preferred details and like that a 5:30 a.m. flight the next morning was booked. Then he even agreed to drive to the airport, take me out for a drink. Jennifer is always talking about building your tribe as you build your real estate portfolio. I also think it is important to surround yourself with people you can trust to not only answer the phone at 11 p.m. but also to help you in a pinch and then drive 30 minutes to meet you for a drink when you’re feeling down.

red osprey backpack on airport floor
My trusty Osprey 46 Porter goes allowed me to save $170 this time.

A couple of takeaways from this:

  1. Traveling carry-on only is my thing. I don’t preach about it because it’s not for everyone but I have done 4+ months with only a carryon and make it work. In this case, it allowed me to buy a $160 flight instead of the $330 flight. I can’t even begin to calculate how much I save in luggage fees not to mention the time not spent waiting for my luggage to arrive. I get off the plane and I’m out of the airport in ten minutes flat nearly every time.

  2. Personally I fly cheap airlines more than I’d like to admit, and this story is the only time I have missed a connection or was in a sticky situation because I booked two separate tickets, so while I lost money in this instance, I am confident I save money in the long run.

  3. You can do the stopover-and-get-off-the-plane move but I have been warned by many blogs that airlines can catch you doing this and there’s a penalty. It was the first time I had ever done it.

  4. And lastly, don’t be friends with someone who gets married at 10 o’clock in the morning. Only kidding, the Denver wedding was a lunch reception, day drinking then dinner with friends and in bed before 11 p.m. After the flights I had just taken to get there, I was happy to go to bed before midnight.

This blog post is a part of a three-part Traveling Hacking series where we share tips and tricks for traveling for free. We focus on real estate investors and believe real estate investing is a great way to create a life you want. Click here to read the entire Travel Hacking series.


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1 thought on “Three Ways to Find Cheap Flights”

  1. Heya for the first time here. I came across this board and I in finding It truly helpful & it helped me out much. I am hoping to provide something back and help others such as you aided me.

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