I’m always hunting for a deal—and honestly, finding a cheap flight gives me an irrational amount of joy.
I’m always hunting for flight deals—and honestly, I still get a rush every time I find a good one. It never gets old.
The first place I always start is Google Flights. It’s the fastest way to see which airlines are running sales and which routes are suddenly cheap. It also gives you a big-picture view instead of locking you into one airline too early.
The first thing you’ll want to do is set your home airport and country. That part matters more than most people realize. I’ll often switch countries or check prices from different locations because many sites use cookies and regional pricing. Sometimes the same flight is noticeably cheaper just by changing where you’re “searching from.”
You can enter exact departure and return dates, but I usually leave them blank at first. I want to see what’s cheap before I decide when or where to go. Let the prices guide the plan, not the other way around.
Right now, I’m scanning flights for Europe and Southeast Asia, and starting with an open search gives me a much better sense of where the real deals are hiding before I narrow anything down.
That flexibility is where the magic—and the savings—usually happen.
My go-to search method
I usually leave the dates blank at first.
This gives me a high-level snapshot of the best prices available right now, which helps set expectations before I commit to anything. It’s especially useful when you’re flexible or just fishing for ideas.
When I was looking at Europe and Southeast Asia, this approach instantly showed me:
The cheapest round-trip prices
\Which cities were on sale
Which airlines were driving those deals
If a price catches my eye, I click into the city, and Google Flights shows:
The exact dates
The airline
How long is that price likely to last
From there, I either:
Book immediately, or
Take note of the price and keep checking until it drops closer to my ideal dates.
I will typically charge the flight to my PayPal credit card. That way, I can pay it off at the end of the month or make minimum payments and place it in the budget down the road.
If you’ve made it this far and are actually paying attention, you’ll notice a pattern: Asia prices were lower last year. That’s exactly why I keep checking and tracking them. Deals come and go—but trends matter.
Flights from Los Angeles to London are almost always a steal. It’s one of the most consistently cheap long-haul routes out there. One-ways are often under $200, and round-trips regularly hover around $500 on Norse Atlantic Airways.
I even spotted a $402 round-trip deal today, which is absolutely worth watching.
The tradeoff with cheap one-way tickets is simple:
You’re gambling on the return price.
Sometimes it works beautifully.
Sometimes it doesn’t.
That’s the cost of flexibility—but it’s also the upside. A one-way ticket gives you the option to:
Stay longer
Change countries
Or fly home from an entirely different city
That’s how one trip quietly turns into a bigger adventure.
In the end, it always comes down to:
Timing
Patience
And knowing when “good enough” is actually a great deal
I also have a bit of an ace-in-the-hole—a friend who can get me home on a buddy pass if things go sideways. Not mad about it.
Last time, she even snagged me an emergency exit bulkhead seat with extra legroom and free drinks. Honestly, that felt like winning the airline lottery without losing half in a divorce.
Moral of the story:
Always have a Plan B.
And if Plan B includes legroom and booze… even better. 
A legend in my mind is the best way to describe it.
I think differently from most people!
I was born in Edmonton, Alberta, Canada, and raised in the early eighties when life was simple. We rode our bikes, played outside, and didn’t have the internet and cell phones like kids today.
Canada was the only thing I knew until my first vacation to Southern California, Las Vegas, and Mexico in my early teens. My first memory of travel was falling asleep under the Christmas tree with the paper airline ticket after reading it 100s of times.
Yes, they used to have paper carbon copies of your actual legs of an airplane return trip, wild!
Just like now, I would tell anyone who cared about my travels (most didn’t and still don’t) that I was going to California, Acapulco, and Mexico (some things never change, LOL)! We drove all around Southern California into Las Vegas and then flew to Acapulco with those initial memories engraved in my mind forever.
Unimaginable at the time, I would later live in Southern California, Las Vegas, and now spend part of my time in Rocky Point, Mexico, and Mesa, Arizona, when I am not traveling. Looking back, I had a plan, and no matter what happened along the way, I would selfishly follow it, even if I didn’t know it at the time of my decisions.
The makings of a solo traveler!
After graduating from high school in Edmonton and trying a few things, my first break happened. I wanted to work with satellites for some unknown reason, so I enrolled in Telecommunications at the Northern Alberta Institute of Technology (NAIT) in Edmonton. It would take me three years to complete my two-year Telecommunications associate’s diploma. I was not the most dedicated student, to say the least, plus my favorite bar was just across the field, Ezzies.
The week before graduating from NAIT in December 1995, I would interview with Canada’s largest Company, Northern Telecom. Looking back, it was a miracle as I was in the bottom half of my class. I aced the interview, and it was the biggest break in my life! I was going to make $13.80 an hour from the part-time $5.50 I was making in 1995; life was good!!
I needed to relocate to Calgary, AB, and started on January 4th, 1996. Within a couple of years, I was traveling back and forth to our Richardson, TX head office, which is a suburb in Northern Dallas. It seemed that I was going there every month, making contacts while falling in love with the American dream. I would board a plane in freezing Calgary, and three hours later, I was wearing shorts! How awesome was that!!
After traveling back and forth, I met someone who was a flight attendant, which again was another sign of things to come.
Eventually, I was offered a job in Richardson, TX, given a work visa, and was traveling full-time.
I bring this up as looking back, she was a major part of my decision to move to the United States. Work would have me crisscrossing the United States and eventually internationally. My girlfriend would follow me and also fly me anywhere I wanted, whenever I wanted.
Holy shit, my dreams were happening! After a few crazy years, it never worked out, but I still thank her to this day when I ask for free flights, LOL. Thankfully, she has a great life raising twin boys along the way!
Little did I know, but these events would severely warp my crazy traveling mind into what it is today. A travel junky who cannot stay put and is always looking for a deal. I was turning into North American Darrell!
My next break was getting a job at PayPal after 18 years at my first job out of college. The job fell in line with my strong beliefs in managing money, so I could eventually travel. It was a great company, a shitty call center job, but it showed some additional money management skills learning through others.
I would get yelled at via email, chat, or on the phone by people being broke-ass douchebag, not being able to manage their money. I could have also easily moved up and might still be employed, but I just didn’t have the piss and vinegar needed. I had health insurance and investments in place, and I was burning time for the Freedom50 traveling dream.
Fast forward, and I was laid off for the second time by a greedy corporation.
Northern Telecom after 18 years in 2014, and now PayPal, 7 years in 2024, 25+ years of service gone after both started cleaning house. Here I was in 2024, unemployed, 52, single AF. I was somewhat financially stable and able to travel whenever and wherever I wanted, again. I started looking back on previous decisions in life.
Almost everyone had a kid, and grandkids, worked 9-5, took their one-week all-inclusive vacation, and spent the summers at the lake. They were living the life we were taught to live by generations. You’re supposed to get married, have 2.5 kids, live in a house with a white picket fence, pay a mortgage, be in debt, retire, and then die. That is just how it works out for the majority of people, and there is nothing wrong with it, but again, I am just different.
Statistically, if you’re a man, you die when you’re 73, if I am lucky to make it that far.
That gives some people 5-10 years of retirement, depending on their health, after working their whole life. I watched it happen over and over in my Telecom career while losing so many family members at a young age as well.
Should I have kept my houses in Edmonton, Atlanta, and Charlotte, where I had some stability?
My first 2,400-square-foot Edmonton house that I designed and built did not have a mortgage. I was able to pay cash from my work travels. I would have been set with no mortgage, surrounded by my friends and family, living like a normal person. I didn’t even use one of the three bathrooms before I sold it, FFS!
Who in their right mind would move on from that situation? 
I could have also settled in other amazing cities that I worked in long-term (Calgary, Dallas, Southern California …)
What about all the other shorter stops along the way (Las Vegas, Austin, San Antonio, Mexico City, Acapulco, and even Brazil)? I had corporate condos for months at a time, met some women and friends, and had a good job opportunity to possibly settle down. There were also so many amazing situations in their way, and I still think about all of them from time to time. I am slowly convincing myself that as we get older, life is a mirage, and we see it the way we want.
Instead, I settled into my small, turnkey, mortgage-free condo that I Airbnb in AZ in 2015 for the long run.
I have always wanted to blog about my travel years of work and personal travel. This is the second attempt, so here we go, again! I hope to share my idea of inexpensive travel through slow travel and geoarbitrage blogs.
Slow travel is a deliberate, unhurried approach to exploring destinations, emphasizing meaningful experiences and cultural immersion. Think of it as living like a local on vacation, where your dollar goes a lot further, geoarbitrage.
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