The Man Behind ‘Scott’s Cheap Flights’ Is Here To Reveal His Tricks

If you were Scott Keyes, you would never have to worry about breaking the ice in social situations. People would slide their arm through yours, linking elbows, and pull you gently to groups of movers and shakers, before asking, “Have you met Scott? Ask him about his flight deals!” You would smile politely, almost demurely — to make yourself seem approachable and not like some smug flight douche — then drop some anecdotal magic. “Well, there were the round-trip tickets to Copenhagen or Oslo for $279, the Azores for $271, Kenya for $310, Rio for $363, and Bali for $348. last week, so I’ll be on the road a lot this spring” And, that would be a sufficient amount of information to elevate you to the upper echelons of party guests. You would always have a full glass and an attractive conversation partner with blindingly white teeth.

In reality, Keyes isn’t spending all of his time flaunting his knowledge or exclusively hobnobbing with toothy world travelers. He’s too busy running Scott’s Cheap Flights, a website and email list that alerts subscribers to inexpensive flights. The former journalist is quite adept at deal spotting and his once small group of followers has expanded beyond friends and family, necessitating the introduction of paid subscriptions to finance the undertaking. Now, it’s a profitable business — thanks to travel industry insiders.

Scott’s newsletter may be one of the travel world’s best-kept secrets, but he isn’t crouched behind a curtain demanding that people pay no attention to him. He’s really open about the methods he and his team use to bring the best deals to their followers. Keyes has hosted multiple Reddit AMAs — giving people the answers they want about cheap travel. And, he sat down with us to talk about great deals, how to find them, and the destinations that offer the best value.

What do you say to a group trip to Lithuania? Let’s start planning now.

Can you give me a quick bio about yourself and your travel background?

Yeah, sure. I’ve always been really into travel, especially after college. I really wanted to be able to travel, and then, I looked at my bank account. On a good day, there were four figures on there. On a bad day, there were two to three figures on there. I knew, “Okay, if I want to travel, I’m going to have to figure out a way to do this without spending much money, because I don’t have much money.” I was a journalist for about four or five, six years after graduating. I knew especially as an entry level journalist, I wasn’t going to be getting rich on that. If I still wanted to travel, I was going to need to thread the needle on those two things.

Therefore, I started to get good at frequent flier miles and also searching for a flight. I developed little tips and trick. If you’re gonna buy a flight, what are all the different steps that you can take to make sure that you’re getting the best price possible for it? In 2013, all that culminated in my getting the best deal that I ever got in my life, which was a non-stop from New York City to Milan for $130 roundtrip.


I know! It was amazing. To this day, I still can’t believe I got to take that trip. It was funny because Milan wasn’t on my radar at all. It wasn’t a place I was dying to go to or anything. But, for $130 there’s nowhere that I wouldn’t go to. And so, I ended up having a great trip. I went skiing in the Alps. I went to a new HRM Soccer game. Went down, hiked Lake Tiempitera, Lake Como, all that sort of stuff. When I got back from that trip that all my friends and co-workers started asking me, “Hey, Scott. Can you let me know next time you find a deal like that, so I can get in on it too?” And then, rather than trying to remember each individual person I was supposed to tip off about these deals, I decided, “Alright, I’m just going to start a little email list.” If I find something decent I can just send it out to everybody at once.

That’s essentially how Scott’s Cheap Flights was born. It was just a little email hobby that I did for my friends sheerly for the love of the game. I just like finding deals and being able to help friends travel. For the first 18 months or so, it was a hobby, something that I did for fun. And it turned into a business, which was the furthest possible thing from my mind. There was never any plans or ideas for that. It wasn’t until about18 months later that it started to get big enough. There were, I think, 5,000 people on the list at that point. Just friends, friends of friends. Like, “Hey, this guy over here, he can find some really good deals. You should get in on this.” At that point, I started thinking, “Okay, maybe there’s actually something here. Maybe we can turn this into an actual business.”

Wow. I’m impressed,

It’s a very weird. I never planned to be an entrepreneur, businessman. If I had planned it, I might have actually taken a class in college on this or read some books on how to make this a business. But for me, I just like finding cheap flights and got good enough at it. It feels so obvious in retrospect that there’s such a demand for people to be able to find cheap flights.

Buying flights is such a weird, opaque process. It’s not like buying a gallon a milk. It’s not like buying a phone case on Amazon or something. The price is constantly changing. You never know what it’s supposed to be for any given route. So much depends on how far in advance you book and what time of the year you book to travel. And, which airline you’re flying and how many stops there are. Even the exact same deal can change. One day, we’ll send out a deal from Atlanta to Amsterdam for $386. The exact same flight, the exact same date, everything, the next day will cost $1,200. Normal laypeople, they’re not spending 24/7 on these flights. How would the average person know this exact same deal was $800 cheaper yesterday compared to today? And so, what we try to do is be that advocate, that concierge who says, “Check out these deals because these are the really good ones. Don’t buy those expensive ones. Let us help you know when the really good stuff pops up.”

Yeah, I interviewed Gilbert Ott of God Save the Points, and he said you have to start following flights and get informed.

It’s a tough thing, because, most people just don’t want to spend their time searching for flights. Right? For most people, flights are just a means to an end. They just want to be able to get through a destination and not spend all their money getting there. They want to have that money at the place to be able eat good food, take cool tours, and stuff like that.

So, you must have all sorts of ‘insidery’ information about how to find inexpensive flights. We know that we’re supposed to be using flight trackers, but other than that, do you have a tiny hint into your process?

Sure! Absolutely! And I think I actually surprise people, how little proprietary process or algorithms or stuff that we use. All of it is just searching by hand eight, 10, 12, 14 hours a day, every day. It’s weird that these really good deals — your $400 roundtrip flights to Europe, your $1,500 roundtrip to Japan — oftentimes they last a few hours. If you didn’t happen to be searching, it’s just like it may well have never existed because you didn’t know about it. And that’s where we come in.

Frankly, I’ve found flight trackers not all that good because airfare’s constantly changing. It’s constantly in flux. The flight checker algorithms, they might run for each person once a day. But it’s not like the price is only set once per day. It’s changing hour by hour, minute by minute, and that’s why we’re always on.

This is one of the tips that I always try to impress on people in terms of being able to really bring the prices down for flights that you’re going to book. Let’s say you want to go to the Greek Islands. You want fly out to Santorini. Typically, if you just go on Google flights or go on Kayak and search for a flight from New York to Santorini, that’s probably going to be about $1200. It’s going to be expensive. That’s just what it is. They say to break it up into two different trips. You search for New York City to Athens; we sent that out a couple weeks ago, non-stop from New York City to Athens for $353 roundtrip. And once you’re in Athens, you can get a flight down to Santorini for $50 roundtrip. So, your overall price is like $400, rather than $1200. You already saved $800, but you can also stay in Athens as long as you want. You can schedule your flight so you have a week in Athens and then a week in Santorini, and then head back to the US.

Yeah. Yeah, that does make sense.

Computers and machines are only as smart as the information we put into them. And it just takes a little bit of human intuition or human strategy. Rather than just searching for the cheapest flights to Santorini, we’re going to break it up in this way in order to get the cheapest flight. And that’s part of the value that we try to bring there. At the end of the day, that’s what people want. They’re not like, “Okay, I have to have everything on one single itinerary.” They just want to be able to get to Santorini, get to Mykonos, wherever, with as little out-of-pocket expense as possible. And that’s employing the strategy for both, that’s what we’re helping them do.

Well it makes sense, given all the work that you’re describing, that it would be easier just to sign up for a list.

I try not to be overly sales, like, “Oh you have to be on a list serve” or something like that partly because I’m not a businessman in LA. I’m not comfortable being sales-y. But, at the risk of sounding overly self-promotional, a lot of the best deals don’t last very long. We’re the eyes and ears, always watching, always monitoring.

Some of the best deals and some of the mistake fares pop up on Friday afternoons, Saturdays, or big holidays: Christmas, New Year’s, stuff like that. Part of the reason why is the people at the airlines who are studying the prices on those are home for the day. They’ve gone home for a Friday. They’re not at work on Saturday. They’re not at work on Christmas. So, when a mistake pops up, they’re not right at their desk able to fix it.

A lot of the times, people will see the best deals pop up that way. We are being ever vigilant, especially at those kinds of off-hours, because sometimes that’s when the best deals can pop up.

You have a lot of access to these really good deals. Do you do a lot of traveling?

Yeah! I do. If I haven’t been on a flight for in the last three or four weeks, I start to get kinda antsy. I feel like I’m stuck in one place, like, “I gotta go somewhere.” I love being able to travel, even to this day. Every time I’m in the flight sitting by the window and just gazing out, I’m like, “Wow, this is incredible. I can’t believe I get to do that.” It’s a very human based instinct, like, “Wow, I’m actually flying right now.”

It’s a lot of fun, the thrill that hasn’t subsided and I just love being able to go to new places, eat new foods, be able to hang around new areas and meet people.

So, benefit us with your great expertise. Where would you say that people should look into traveling in 2018? Give us places with the best value. Trying to save on your trip, where do you go?

Eastern and Central Europe are a really, really good value. I recommend both Czech Republic and Prague. I have always been very skeptical of places that have a high reputation ’cause I just like I’m going to go and be disappointed; it’s not going to live up to the hype. Prague lives up to the hype. It is an incredible East meets West city. It’s way cheaper than the UK or Germany, certainly than Scandinavia and Austria. But, it still has a similar vibe. The food and beer are incredibly tasty. It has pretty natural landscapes and a great sort of train infrastructure. It’s easy to get around and a lot of cool places to see. There’s just a ton of history, both more modern World War II cult war era history and then much farther back.

Another one is Lithuania. This was not on my list at all. I had no idea, but a couple years ago my wife and I took like a round-the-world trip together. And, we were trying to pick out places to go. We came to Lithuania, and she was like, “What about going there?” And I was like, “Okay, I’ve never heard much. It’s not on many traveler’s maps or on their radar.” But she was like, “Well, Lithuania supposedly gets rated as having the most attractive people in the world.” Okay, I guess that’s as good a reason as any. Let’s go check it out. And it ended up being this hidden gem of a country. It’s similar to Prague with the sort of East meets West feel. Really good food. Really friendly, welcoming people. Beautiful architecture. The weather in the summer is incredible. Inexpensive, especially compared to other parts of Europe. And overall just interesting, sort of, more natural things to do there.

We took a train out to the coast, place called Klaipèda. There’s a UNESCO spot, called the Curonian Spit, which is essentially this massive, peninsula. I think it’s technically called The Spit, which I didn’t realize is the name of a type of island formation or something. Just think of like a really long barrier island, like 60 – 70 miles long, where you can go and it’s forest right next to sand dunes; you can rent bikes and ride through it. You can ride down to Russia there. It’s a bizarrely interesting spot that I had no idea about and then just had a blast exploring. Lithuania is one of the ones that I always recommend for folks.

The Baltics in general are an incredible part of the world that, I think, is not on enough traveler’s radars.

Awesome. I love that you not only named places, but you’ve had substantial reasons. I want to go to Eastern Europe now.

I know and it’s such a cool part of the world. Like I want to go back and explore more. Also your dollar can go so much further in that area, than if you are in Germany, Denmark, or Heaven forbid like Norway or somewhere. You’ll be able to spend a month in Lithuania on what it would cost you to spend a week in Norway.