Scoring Cheap Airfare With Scott Keyes

The founder of Scott’s Cheap Flights newsletter joins the show with strategies you can use to save on travel. Also, our hosts Ryan Ermey and Sandra Block talk streaming options for those thinking of ditching their cable service.

Ryan Ermey: We know you're already thinking about going home for the holidays and on a fabulous vacation in the spring, and because we know you want to save on airfare, we went straight to the source. Scott Keyes, founder of the popular email newsletter Scott's Cheap Flights joins us for our main segment.

Ryan Ermey: On today's show, Sandy and I discuss strategies for ditching your cable provider and delve back into our wackiest PR pitches. That's all ahead on this episode of Your Money's Worth. Stick around.

Ryan Ermey: Welcome to Your Money's Worth. I'm Kiplinger's Associate Editor, Ryan Ermey, joined as always by senior editor Sandy Block. Sandy, are you ready for some football?

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Sandy Block: No, Ryan, because I am still getting high on baseball. The Nationals are hot, so I'm not ready for football yet. I'm all about baseball right now.

Ryan Ermey: My beloved Phillies are less than hot, but maybe they will have turned things around by the time this comes out. Of course, by the time this comes out, football season, NFL football season will have commenced and this will be coming out simultaneously with "Monday Night Football," hence the question.

Ryan Ermey: And to me, football season is all about enduring hundreds of advertisements for Fox and CBS's fall lineups. So I tend to think of fall as the new season for TV. And we just wrote about something that we've really been covering for years at Kiplinger's, which is this idea of cutting the cord.

Sandy Block: That’s right. The idea that you no longer have to rely on cable to get all the programs that you need, and that you can save a lot of money by looking for other alternatives.

Ryan Ermey: And really in the not so old days, cutting your cable, you ended up with sort of very limited streaming options, but now there are dozens of services to choose from and people are coming up with ways to watch only the content they want, perhaps for cheaper than paying for the big cable package.

Sandy Block: Because that was always one of the biggest complaints about cable is that you got stuck. You ended up paying for all these channels that you didn't want. They would say, "Lucky you. We've added the golf and tennis channels for just an additional $10 a month," and you don't play golf or tennis and you don't care.

Ryan Ermey: Very popular channels in my parents' households, both avid tennis players and golfers, but the point stands. And the average household using pay TV spends about $105 a month on cable.

Ryan Ermey: Now, some companies, some cable companies I should say are offering sort of more narrow packages for cheaper to try to retain customers that are otherwise fleeing to streaming services, for say around $50, but then you're still locked into a contract.

Ryan Ermey: You are still hit with fees, and you're still subject to rate hikes when whatever introductory offer that you inevitably take expires. Now before we get into where you might want to do your streaming, it should be mentioned that a lot of times people bundle their cable and internet-

Sandy Block: And phone.

Ryan Ermey: ... and phone, and at least in D.C. it's like if you wanted to drop the cable and the phone and just do internet, it's probably not that much cheaper. You're probably still paying a lot of money. And then to add a streaming service on top of it might be more expensive.

Ryan Ermey: So you're going to have to do some comparison shopping, and what you should do and what our colleague Kaitlin Pitsker recommends doing is start by making a list of networks and programs that you watch. There's a website that helps you to do this,, where you can see where your favorite or soon to be favorite... I always have a list of 10 to 15 shows that people tell me I just have to be watching it.

Ryan Ermey: I'm like, "What am I doing?" And just to see where they're offered. And like I mentioned before, you are going to need to hang onto your internet, probably a speedy one and a streaming device. So you'll need an Amazon Fire, Roku, Chromecast, which is Google's product, or some kind of Smart TV.

Ryan Ermey: And you're going to have to weigh whether you care about having live TV in addition to on-demand programs. For a long time not having cable and going 100% streaming was not a viable option for me because I need live sports.

Sandy Block: Right. Sports was always the wild card here, if you wanted to... Same way with us with baseball. There wasn't really... You didn't have cable, you'd have to listen to it on the radio.

Ryan Ermey: So one of the things that we've recommended from the very beginning is seeing what you can get in terms of an antenna. Now the connectivity isn't going to be the same everywhere, but in certain places you'll be able to get more than you could get with basic cable for a onetime cost. You pay for the antenna, which is relatively cheap. We have a couple that we recommend.

Ryan Ermey: One kind of a cheaper one, one on the high-end range, but even the high-end range is like less than 200 bucks, and you pay one time and then you [get] broadcast to just like you did with your old rabbit ears.

Sandy Block: Yeah, old school.

Ryan Ermey: Yeah. Otherwise the prices for these streaming services vary. Among the ones that offer live TV, you have AT&T, TVNow, which is formerly DirecTV. Now that's 50 to 70 bucks a month. Hulu + Live TV, if you've seen my guy Joel Embiid who plays for the Sixers, Hulu has live sports.

Ryan Ermey: That's $45 a month, Sling TV, $25 to $40 a month. YouTube TV, $50 a month. Now they come with add-ons for certain channels, so you're going to have to look around and see what is out there. Like for instance, I need TNT, because I watch the NBA and they're one of the major broadcasters of the NBA.

Ryan Ermey: You might have to pay extra for that at one place and not at another. And then you have the on-demand TV and movie services. Now, do you have any of these?

Sandy Block: No. Well, we have Amazon Prime and we have Netflix.

Ryan Ermey: Well, that's is two of them.

Sandy Block: One thing I really like about all of these streaming services, particularly since there's so many choices, is unlike cable, you pay them by the month. And a lot of them will let you try them out for free, but even if you subscribe, you could only have TNT during basketball season.

Sandy Block: One thing I've thought about doing and haven't done, but I mean to next year, is just suspending Netflix in the summertime because I'm not around, I don't watch TV in the summer. You could just suspend it for the summer months and pick it back up once the snow starts to fall. So I think you have a lot more flexibility with these streaming services and it does give you the option of trying them out to see if you like them.

Ryan Ermey: So, as always, the advice is to see what you like, see what fits into not only your budget, but into your household's watching habits. Another thing to consider is how many simultaneous streams they'll let you have, how many users they'll let you be on there. I mean I know people using all of their parents'.

Sandy Block: I know people have more people on Netflix than we got in the office right now. But yeah, definitely.

Ryan Ermey: So that's worth checking out. And the last thing that I wanted to note is that there are a few of these streaming services that are free, and why not see what's on there? You have Hoopla and Kanopy with a K, because obviously you can't have it...

Sandy Block: It's cool.

Ryan Ermey: You have to have some sort of-

Sandy Block: Because it's cool with the K.

Ryan Ermey: Yeah. But it's especially cool because they're both offered through your public library.

Sandy Block: There you go.

Ryan Ermey: And they have movies, TV shows, music, audio books, eBooks, and that's all free. And so, I mean, is it going to be the brand new "Avengers," whatever, for free? Probably not. But you may find a movie on there that is good enough for your Friday date night. Sony Crackle, IMDb TV, Pluto TV and Tubi. That's a little... T-U-B-I.

Sandy Block: Who makes this stuff up?

Ryan Ermey: Also have free stuff, but you'll have to watch commercials along the way. Now for people like you and me who grew up watching TV with commercials, that's no problem. My nephew who's 10 years old cannot abide a commercial.

Sandy Block: There'll be none of this. I guess he never has to go to the bathroom.

Ryan Ermey: No. Maybe like a YouTube ad. I mean for me it's like if a movie's on TV and this is like the... If a movie's on TV with commercials it's going to be like a third longer. It's also something I can probably stream or get online or whatever.

Ryan Ermey: But there's something fun about flipping around and like catching it halfway through and then watching all the way through with the commercials. Now the nice thing about the commercials is exactly, you can get up, go to the bathroom, go throw a load of laundry in, or you decide, "All right, next commercial break, I'll go outside and do yard work."

Ryan Ermey: So anyway folks, make sure to check out Kaitlin's entire story. It's in the October 2019 issue of Kiplinger's personal finance magazine on newsstands now... Coming to you soon folks. If you don't have it, get it and see all of the great things that she talks about there and we'll be sure to put it up in the show notes as well.

Ryan Ermey: All right, we are back and we are here with Scott Keyes, who is the founder of the, I would say ubiquitous, cheap flights newsletter, Scott's Cheap Flights. Scott, thank you so much for coming on.

Scott Keyes: Thank you so much for having me.

Ryan Ermey: So we actually, we did a Q&A, you and I, in the magazine a few years ago. And at the time you said that flexibility was really the key to finding good deals on airfare. Why is that?

Scott Keyes: Yeah, I like to say flexibility is really your friend and here's why. The way that most people go about searching for flights is a three step process. Step one, they decide where they want to go. Step two, they decide when they want to go, and only on step three do they look at what are the flight prices like.

Scott Keyes: And by setting price, by setting airfare as the third order priority, they end up getting not very good flights. So if you're someone like me who really has dozens of places they would love to go and really wants to make sure they get a cheap flight doing it, what I recommend is actually flip that search process on its head.

Scott Keyes: Set the first order of priority, where are there cheap flights, and then in step two and three decide, of the places where there are cheap flights, where do I want to go and when do I want to be there, and when are there available cheap dates that I can go there?

Scott Keyes: Do any of those work with my schedule? If so. Great. And so to give you a concrete example, I sent out a deal just yesterday that had availability from all over the U.S. to Amsterdam nonstop for 477 bucks round trip. If you had searched on those exact dates to London rather than Amsterdam, fares were 927 bucks round trip.

Scott Keyes: And so if you had had just your head like sort of narrowly focused on London, you would have ended up paying 450 bucks more than if you had said, "I'll go somewhere where it's cheap in Europe." And even if you're really set on getting to London, buy that $477 flight to Amsterdam and then just book a train, or book a cheap flight from Amsterdam to London.

Sandy Block: So Scott, we're not that far out from the holidays and sometimes people really do have a specific destination, they don't have any choice. So what's the ideal window for buying airline tickets? I mean, for example, how far in advance should you start searching for a flight?

Scott Keyes: What I recommend for folks is that if you're searching for domestic flights, kind of one to three months ahead of time, if you're looking at international flights, two to eight months ahead of time. That's the window when cheap flights are most likely to pop up. So you don't want to book just any old fare during that window.

Scott Keyes: You just want to know that that is when cheap flights are most likely to pop up, and when I should anticipate getting ready to book. If you're looking to travel during a peak holiday period, so right around Christmas, New Year’s, or domestically for Thanksgiving or even in the middle of summer, I would add a couple of months to those recommendations as well, because it's that much tougher to find cheap flights during the holidays or peak travel periods.

Ryan Ermey: And so I also seem to remember talking with you about using a tool such as Google Flights that can expand the number of departure and arrival destinations, as well as sort of look at a range of dates.

Scott Keyes: That's right. That's right. And this goes back to what I mentioned about flexibility, where on Google Flights you can put in up to seven airports at once. And by doing that I can say, "Okay, from my home airport, what is the cheapest to fly to Amsterdam, Paris, Rome, Barcelona, Madrid, Frankfurt and London?"

Scott Keyes: And it'll tell me instantly, "Okay, you've those seven cities, the cheapest is Rome for 305 bucks round trip on September 8th through 15th," or something like that. Like it'll tell you that quickly and that instantly what is your best bet among all those options?

Scott Keyes: And then you can decide for yourself, "Hey, does that sound like a good place to go? Do I have that time off in my schedule?" and whatnot. But at least having that knowledge of when the cheap flights are available I think tends to be really valuable information for the cheap flight aficionados among us.

Sandy Block: So Scott, every time any of us budget travelers get on a plane, we walk past the people in first class or business class or even premium, and just envy those people and we go back in the back and sit in the tiny seats. Are there certain times that it might be easier to find good rates on those nice seats?

Scott Keyes: In terms of trying to find the cheapest premium seats, whether it's a premium economy or business or even first class, the fares typically tend to behave similarly to economy fares, but just in order of magnitude higher.

Scott Keyes: So you're still going to want a book well in advance, not wait until the last minute. You're going to typically find better premium fares if you're flying on a more uniformly leisure route than one where there might be a bunch of business travelers.

Scott Keyes: So if you're flying from New York to London, that business class seat is almost certainly going to cost more than one from New York to Honolulu. You're not competing with all the corporations who don't care what the price is, they're going to put their executives in those business class seats.

Scott Keyes: And so I would think about it less in terms of timing and more in terms of routes, which ones are most likely to see a drop, and the more leisure your destination, the better your chances of getting a good fare there.

Ryan Ermey: You mentioned business travelers and I seem to remember that because of business travelers it's sort of a myth that you can get a deal if you book at the last second. Are there any deals to be had if you're booking last minute?

Scott Keyes: That's right. A couple of decades ago there were, it was a common thing that airlines would try to slash their fares in the days leading up to a flight because they made the calculation that look, as soon as you close the airline doors, any unfilled seat is just lost potential revenues.

Scott Keyes: So how do you fill as many seats as possible? You slash the price. I was actually reading an academic paper that really changed the trajectory of this, where they surmised that look, maybe we shouldn't be optimizing for trying to fill the number of seats, and this is from the airline's perspective, maybe we should be trying to optimize for the amount of revenue we make.

Ryan Ermey: We're back and before we go, a segment that we haven't done in a little while and it's certainly our favorite to research, and that would be wild pitches, more tails from our wackiest PR pitches. And Sandy, why don't you go ahead?

Sandy Block: Okay. Mine comes from someone who calls himself the Zen Millionaire and I'm sure that millionaire ranks high on SEO because I'm always getting pitches from like the millionaire mom, the millionaire motorcyclists.

Sandy Block: Well, this is the Zen Millionaire and this individual basically views himself as sort of the Marie Kondo of money. And basically what he says is that if you treated friends like you treat your money, would they still be around? And his whole pitch is that you should imagine money is a person. He says, "Now that might sound strange." Yes, it does.

Ryan Ermey: It sure does.

Sandy Block: But imagine for a moment that money is a person. Would this person want to be around you if you are filled with dread, stress and worry every time you're with them? Would they stick around if you treat them with cold detachment? Of course not. And money is the same way. So the pitch is that if you treat money with respect you'll have more of it.

Sandy Block: And this is kind of a genre that we get a lot. Basically all you need to do to make more money or get rich is to change the way you think, just embrace money or make friends with money or shake hands with money or something like that. And when I think it gets away from is managing money is hard. That's why we have a whole magazine devoted to it.

Sandy Block: You have to figure out how to invest, how much you can afford to save, what your budget is, and many, many decisions you have to make. Buy or rent, these are hard decisions that oftentimes they involve math really. Just sitting down with a calculator and figuring out what you can afford, how much you're going to earn, and no matter how you feel about money, whether you make friends with it or not, you have to do these things to get more of it and to save more and have a secure retirement.

Sandy Block: And I think just basically trying to tell people that if they make friends with their money, they're going to be fine overlooks the hard work that most of us have to do.

Ryan Ermey: Yeah, you don't have to break out your spreadsheets when deciding whether you want to go get drinks with your friends. You can just go. It is fun. Spend time with them and being good with your money is being disciplined with your money.

Sandy Block: Right.

Ryan Ermey: So I've received several pitches and I'm not sure if it's like this time a year or a lot of people out of the office, late August pitches, all the mutual fund guys. As I found out reporting my other stories, it seems like all of Wall Street goes to the Hamptons in August.

Ryan Ermey: So maybe these are the investing pitches that make it into my inbox. But I've gotten several that are about investing in fractional shares of collectable or antique, I guess not antique, but collectible things with intrinsic value. So this says... Headline is, investors are buying stock in old comics and Pokemon cards.

Ryan Ermey: Most of us probably know an 11 year old who blew their whole allowance on a pack of Pokemon back in the day, but boiling stacks of cash on Pokemon cards isn't just for preteens anymore.

Sandy Block: No, it's for dumb adults.

Ryan Ermey: You can do it too. Well, we have another one. Have you ever predicted a rookie quarterback would be way better than everyone else expected?

Sandy Block: No.

Ryan Ermey: Now what if you could turn that knowledge into real money? A fantasy-sports-driven stock exchange, and look, all right, so I looked into into one of these and I'm not going to say the name of it because I don't want to blow up their spot, but they've raised $2 million in funding and they want to expand their market place of rare collectibles. And recently for just $45, investors can purchase a piece of a Magic The Gathering card that's worth $90,000, or so they say.

Sandy Block: So they say.

Ryan Ermey: And that's the first edition, the alpha edition, Black Lotus. I used to play Magic cards. I know all about Magic.

Sandy Block: I'll take your word for it, man.

Ryan Ermey: Although didn't play far enough back to have given myself a chance at the Black Lotus. But the deal is this, if you have 500 shares of Amazon or Walmart or McDonald's, I mean the value of your share is going to fluctuate based on what investors think of the company and the value of the company is driven by things like earnings, underlying fundamentals.

Ryan Ermey: What a Magic card is worth, I mean, you're just being told it's worth $90,000 and all of us have watched “Pawn Stars” or “Antiques Roadshow.” Someone comes in and says, "I was told this was worth $10,000," and even the appraiser might tell you it's worth $10,000, but it's not worth $10,000 unless someone is willing to buy it for that.

Ryan Ermey: And so the huge issue with this is that they say that they're going to be able to, once they have all of these shares, if this magic card sold, they're going to create like a secondary market for people to trade shares of it. But that, I mean, what we're talking about here is such a lack of liquidity.

Sandy Block: Right, or transparency, because how do you know that it's worth what they say that is worth? There's no stock exchange to go to, no annual report to look at to figure out whether this is actually what the item that you're buying a fractional part of is worth.

Ryan Ermey: And once again, watch “Antiques Roadshow” and they'll tell you this piece of Japanese art, anything that's rare and collectible, this piece of Japanese art or these Nike sneakers from 2006, I mean they say, "It's worth $10,000 now, but 10 years ago you could've gotten $30,000 for it."

Ryan Ermey: And the reason is that what people are willing to pay for certain collectibles, it changes completely and it's not like these things are going to appreciate forever. Like investing broadly in the stock market, in the U.S. stock market has meant that that's going to go up over the long term forever, as far as we know.

Ryan Ermey: That is not the case with Pokemon cards. I remember thinking that I had some very valuable Pokemon and Magic cards when I owned them, and I think I sold them all for a song. So normally with these situations I say, don't invest any amount of money that you're not completely willing to lose.

Ryan Ermey: In this case, stay away from this one, please. Just don't put your money in Magic cards unless you're a professional, maybe that's the caveat, if you're a professional dealer in Magic cards or Pokemon cards and you know for a fact what these things are or worth-

Sandy Block: Then why would you need a middle man?

Ryan Ermey: Right, exactly. Just don't do it folks. Okay? There's so many other things. That's it for this episode of Your Money's Worth. For show notes and more great Kiplinger content on the topics we discussed on today's show, visit

Ryan Ermey: You can stay connected with us on Twitter @kiplinger, on Facebook at, or by emailing us at, and if you like the show, please remember to rate, review and subscribe to Your Money's Worth wherever you get your podcasts. Thanks for listening.

Sandra Block
Senior Editor, Kiplinger's Personal Finance

Block joined Kiplinger in June 2012 from USA Today, where she was a reporter and personal finance columnist for more than 15 years. Prior to that, she worked for the Akron Beacon-Journal and Dow Jones Newswires. In 1993, she was a Knight-Bagehot fellow in economics and business journalism at the Columbia University Graduate School of Journalism. She has a BA in communications from Bethany College in Bethany, W.Va.