Autopilot Monitors Flight Price Drops After Booking | Save Money, Cash & Points | Sam Hollander Interview
Justin Vacula of the Hurdy Gurdy Travel Podcast interviews Sam Hollander from Autopilot about how travelers can track flight price drops after booking and potentially save money, receive travel credits, or rebook award flights for fewer points.
Autopilot helps monitor eligible flights booked directly with supported airlines, making it easier to spot lower fares without manually checking prices every day.
Sam explains how the idea for Autopilot came after many airlines reduced or removed change fees, why repricing opportunities are often missed, and how the platform works for both paid tickets and award travel.
Autopilot affiliate link: https://www.withautopilot.com/?partner=HurdyGurdy
In this interview, Justin and Sam discuss supported airlines, how to import reservations, privacy considerations, common savings opportunities, how Autopilot compares with competitors, upgrade alert features, and upcoming plans for hotel repricing.
Whether you book flights with cash, points, or miles, this episode covers a useful travel tool that may help you save money after you’ve already booked. Subscribe to the Hurdy Gurdy Travel Podcast for more interviews, travel tips, points and miles strategies, loyalty program updates, and ways to save money on travel.
Timestamps:
00:00 Podcast Intro
00:32 Meet Sam Hollander and Autopilot
01:13 How Autopilot Got Started
03:06 How Autopilot Works
04:39 Importing Flights and Tracking Prices
05:52 Eligible Flights and Savings Opportunities
07:44 Big Savings and Real Price Drops
10:13 International Flights and Airline Partners
12:03 Privacy and Security
13:30 Break and Links
16:19 Competitors and New Features
17:31 Upgrade Alerts and Hotel Repricing
19:51 Travel Plans and Final Discussion
21:51 Credit Cards and Outro
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Rough Transcript:
Travel at low cost with points and miles. Credit card rewards bring the smiles. Many adventures tales to be told, make and save money, the world will unfold.
Fight the war on happiness, pick up the gold. Hurdy Gurdy Travel Podcast breaks the mold.
You’re listening to the Hurdy Gurdy Travel Podcast, I’m your host, Justin Vacula, here to help you make money, save money, and travel the world at low cost with credit card points, miles, benefits, and loyalty programs. Today’s special guest is Sam from Autopilot at withautopilot.com, Sam joins me to talk about his tool that alerts you to price changes on already booked flights, to save you points and cash.
Discover how autopilot will [00:01:00] save you time, points, and money. On with today’s episode recorded, March 18th, 2026. Welcome to the show, Sam. Thanks so much for having me, Justin. Really excited to be here. How did you get involved in this space in miles and points? Going years back, I had been on a family trip and my father told me that he used credit card points.
On my 18th birthday, signed up for my first credit card and have been really maximizing the game ever since.
I’ve also been an entrepreneur. I’ve been building businesses really since high school when I started a small business marketing agency for mom and pop stores which eventually transformed into building tech companies in college. Outside of college, I started a few things in the travel space and most recently have been working on autopilot.
So happy to talk a little bit more about the founding story and how we got specifically to autopilot, but that’s a little bit more about my [00:02:00] background and how everything led up into autopilot. Excellent, and thanks for connecting with me. To be upfront with listeners, I’m now an affiliate with Autopilot.
I’ve received various emails in just a few weeks about flights I had booked, saved 7,500 miles. 2,500 miles, 1000 miles. These were on American Airlines flights, and the email notifications say you can cancel and rebook your flight to save points. Yeah, we love when our members save money and also love when our members save points.
We started autopilot late 2023, but really early 2024 and airlines eliminated change fees. that allows them to essentially price match when the price goes down after they book. I have friends family who didn’t really know that this was a thing.
But once they found out about it. They were like, yeah, this is really cool, except I don’t really have the time to track the prices to claim the price drops when they come. And that’s where I saw a ton of opportunity.
We’ve saved a ton of money in [00:03:00] cash flights already. But again, just really excited to hear that you’re already seeing the product at work.
For people new to autopilot, can you walk us through the process step by step if they were to sign up for the pro membership for all the features. Yeah.
Before we go into pro, I think it’s helpful to start and talk about autopilot on the pay as you go plan, because that is our bread and butter. A lot of customers love coming to autopilot and tracking their flights and only paying when they save.
If you wanted to sign up for autopilot today, you can go to withautopilot.com. Once you sign up, we’ll ask for some basic information just to make sure that we have all of the accurate information for you. Then you’ll be prompted to add reservations into autopilot. If the price drops anytime between now and departure, we will work with the airline to claim a lower fare credit for you.
It’s only pay when you save. So if we save you nothing, it’s completely free to use. And when we do save you [00:04:00] money, we charge 25% of the amount that we’ve saved. We do also have a pro plan. If you do book an award reservation, we don’t automatically reprice it on the pro plan, but we do send you an alert with very clear cut instructions as to how to claim the lower fare yourself.
Also upgrade offer alerts and a few other different features on our pro plan, and I have the affiliate link. It’s withautopilot.com/?partner=HurdyGurdy, and that’s in the show notes. Listeners can click there if you like what you’re hearing, and you’d like to sign up.
You link your Gmail, your flights are already booked in your Gmail, and then it scans. How does that process work? When you’re prompted to add flights during onboarding, there are three ways to import your existing reservation.
The first and the one that most customers prefer just because it’s easiest, is to link your Gmail account. And when you do what [00:05:00] we do is we will essentially go through and only pull in your travel confirmation emails from various travel providers and add those reservations into your autopilot account.
How often are the prices checked? Is it something that just checks day by day at a certain time in the day? Yeah, so prices are checked constantly, multiple times a day throughout the day. There are very predictable times that airlines change prices of their reservations or of their flights. And autopilot essentially has a lot of that data to suggest, Hey, when is the airline going to change the price of this reservation? And we’ve built proprietary software to make sure that we get price drops, essentially as they are published through the airline.
We use some software to help us do that. And yeah we check multiple times a day. I’ve mentioned using American Airlines points. Might this work if someone books through the Amex travel portal, the [00:06:00] Chase travel portal, other integrated things in points and miles. One of the qualifiers to use autopilot is the reservation must be made directly with one of our supported airlines.
If you book a reservation through an online travel agency, through a traditional travel agency or through one of the credit card portals, for example, the Amex portal or the Chase travel portal, we aren’t able to support the reservation. However, if you, for example, purchase the flight directly with the airline through delta.com, whether it’s booked with cash or points, we are able to support and track that reservation for lower fares.
What might the average savings be per user? Assuming someone might fly maybe once every two months, maybe once every month, or the more frequent travelers? Yeah, it all depends and unfortunately there’s no good ballpark number that we can give just because travelers often segment into very frequent [00:07:00] or, moderately frequent or
infrequent. We have families that travel once or twice a year. Maybe we can save them, call it 20 or 25% on their flight reservations. However, we also have frequent travelers who are flying weekly or bimonthly, and we’re able to save them a lot more just as a function of their being more volume and us being able to track those reservations
for a lot of time. It all depends on the customer and their travel patterns, but we do support and are able to save customers all across the spectrum, whether or not you travel once a year, 20 times a year, or anything in between. Yeah. What are some of the biggest wins that you’ve had through the tool or perhaps some customers?
Personally, I don’t spend a ton of cash on flights just because I’m an avid points and miles person. But just two weeks ago I saved about 20,000 [00:08:00] miles on a united flight, which I was super excited about because the total cost of the reservation was about 50,000 saving a good 40% on the reservation.
And there have been reservations where we’ve saved customers on the order of thousands of dollars, and that’s always very exciting because we love to see customers save money. And we often see those customers using that money almost immediately for a new trip that they’ve been eyeing and maybe didn’t wanna outlay the cash to book, but now they have a little bit of a travel credit that they can go and book towards a new trip.
We always love seeing customers essentially use the money that we’ve saved to go and travel more. How many flights might drop after booking? What percentage of flights? Say someone were to take 12 flights a year? How many of those on average do you think might change? Yeah, generally speaking we’d say about 50% of those flights would drop.
Of course there is a lot of nuance there. That is a general rule of thumb. For [00:09:00] example, somebody who’s flying in international business class, those prices are generally a little bit more volatile than a short haul domestic economy ticket. However, same thing if you’re booking six months out, it’s a much different answer than if you’re booking week of and it all depends on the traveler, but if you’re booking call it six to eight weeks before for domestic, or three to six months for international we feel pretty confident that at least half of those are gonna go down in price, at least by some amount between the time you book and the time you depart.
How about domestic flights? Are listeners going to get a lot of value out of rebooking domestic flights? Absolutely. Domestic flights are our bread and butter. You most certainly can save money on domestic flights, even in economy, short haul.
It’s all a game of percentages. And 20% of a thousand is greater than 20% of 200. And even if the prices do go down, we are able to save customers money no matter if it’s a domestic [00:10:00] short haul economy ticket or a long haul international first in business. It’s more just a question of the volatility of those prices because there’s just more volatility in long haul international and or premium cabin tickets.
International usually gets complicated because of transfer partners. If I were to transfer American Express membership rewards, for example, to different programs and something were to change their cancellation or change policies might not be as good, but maybe using something like Delta, I’ve booked Delta one several times with flash deals for good value on international flights.
How might that work for international dealing directly with the carrier or transferring points? Yeah, great question. Autopilot supports tickets that are booked on the carriers that we support, and those carriers are Alaska American, Delta, JetBlue and United.
So for example, if you are flying on British [00:11:00] Airways, but you have purchased that reservation through American Airlines, we are able to support it. Now, on the inverse, if you are flying on American Airlines, but you purchased it through British Airways, we are not able to support it.
As we think about international carriers as long as it was booked through one of our supported carriers, we will be able to monitor the reservation for price drops on either cash or points. However, if it was booked with a partner of one of our supported airlines, unfortunately we are not able to track it for price drops.
Good. I imagine that without autopilot it could be quite tedious. Maybe setting a calendar notification, check, maybe once a week on existing reservations, and then even if you do that, you might not see the discounted fares. Certainly would take a lot of time, I imagine. I’d be interested to hear from listeners in the comments you’re on YouTube to talk about your experiences with rebooking, if there are price adjustments or if you are an autopilot [00:12:00] user and you’ve had some success.
We’ll talk about the privacy and security. What exactly are you accessing in email with autopilot? When a customer opts in to link their Gmail, which they don’t need to do to use our service, I know there are some services out there that require a link Gmail. You do not need to link a Gmail to use autopilot.
When you do, we pull in your travel confirmation emails so that we can essentially take the confirmation number and then put that into your autopilot account. That is purely, again, an ease of use thing, and so customers don’t need to link a Gmail in order to use autopilot.
If you wanna start by giving us one reservation to, to track and monitor, you can do that by manually importing or just forwarding that one reservation confirmation to trips@withautopilot.com and we will track just that one reservation. Privacy and security is something that’s top of mind for me. I am in my free time a cybersecurity nut.
[00:13:00] I wanted to make sure that we built autopilot in a way that no matter your level of comfort, no matter your level of wanting to be as secure and private as possible, or, opting for the easiest user experience, we have solutions for you to be able to use autopilot. Very good, and once again, the affiliate link is withautopilot.com/?partner=HurdyGurdy. That’s also in the show notes.
We’ll take a quick break and come back to discussion of autopilot. For more content between shows, follow Hurdy Gurdy Travel Podcast on Facebook and x. Follow Justin Vacula on Instagram. Subscribe to Hurdy Gurdy Travel podcast on YouTube for daily content, including travel videos, podcast clips, and posts.
For more information including episode transcripts, go to HurdyGurdyTravel.com. And Sam, where can people find autopilot [00:14:00] and perhaps you on social media? People can find autopilot at WithAutopilot on Twitter and Instagram, and people can find me at. On X at Sam Hollander. And if you could spell your name, please.
S-A-M-H-O-L-L-A-N-D-E-R. Excellent. And if you are in the greater Philadelphia area, I have a meetup group meetup.com/PhillyMilesAndPoints. RSVP for monthly meetups. The next ones in 2026 are April 19th and May 9th. May 9th is a special meetup featuring Rove and Carissa Rawson past podcast guest.
Find a link in the show notes. Sam, any meetups in your area or will you be attending any in 2026? None that I know of right now. But doing in-person events is something that’s very much on my radar excited to start doing them soon. There’s FTU Dallas [00:15:00] coming May 1st through the third at the Nylo Las Colinas hotel by Hilton near the DFW airport.
Join us for social events, educational sessions. Ticket sales are live. Grab an FTU annual membership for online courses, monthly virtual seminars, member perks, event discounts, and more. Use my FTU affiliate link in the show notes for membership and conference tickets. Maybe we’ll see you there or a different event during the year.
Thank you. Yeah, excited to see you. I’m also a proud affiliate with CardPointers. If you have multiple credit cards like me, because the answer to everything is more credit cards, the CardPointers app and browser extensions automatically activate bank offers and know which card to use for maximum rewards. CardPointers saves me time and money.
Use my link in the show notes CardPointers.com/HurdyGurdyTravel for discount annual and lifetime plans. I’m also an affiliate with SaveWise. SaveWise helps you automate [00:16:00] clipping grocery coupons at Acme, Kroger, and about 5,000 other stores. SaveWise also helps you compare shopping portals and offers and has many other features.
Use my link in the show notes. GetSaveWise.com/HurdyGurdy. Returning now to the show . Thanks again for joining me. Absolutely. Thanks for having me.
Autopilot. There are some competitors in the space. How does Autopilot stand out from competitors? We started a little over two years ago at this point, and have been single handedly focused on building the best customer experience for repricing travel after they’ve booked. There are other competitors and tools out there.
I think some of them are free ranging from Google flights as a do it yourself option. I know that Capital One has their price guarantee if the price goes down after you’ve booked through them. However, we wanted to build a solution that allows customers who are booking direct [00:17:00] to have the ability to manage their reservations after they’ve already booked. We’ve seen a lot of investment in the booking space, not a ton of investment in the post booking space. We set out with how do we help customers and travelers get the best post booking travel management solution that they can.
That’s really what we’ve been building. And of course there are a ton of other players in same space, a slightly different space, but we are single-handedly focused on building a post-booking automation solution. What are some features that might be coming in the near future?
One feature that’s already live that we’ve seen a ton of positive feedback from our existing customer base is upgrade offer alerts. Airlines, if you’re an elite member, you’ve probably noticed, especially over the last three to five years that complementary elite upgrades to first class are unfortunately
slowly going away. And that’s a function of the airlines now selling these [00:18:00] upgrades or these essentially upgraded seat assignments at a very affordable price. You might see the price to go into a first class seat on a short haul domestic flight, especially last minute dropped to anywhere between, 50 to $200, which for many people
is something that’s worth it. We have built a monitoring solution for these upgrade prices. So you can say, Hey, I’m flying JFK to LAX. I wanna fly in premium select on Delta. Can you let me know if the price to upgrade drops below, for example, $300? And Autopilot will continuously monitor that personalized upgrade price.
And if the price drops, we’ll send you an alert. Now we also recently launched a tangential product here, which allows us to process the upgrade on your behalf. Hey, instead of you alerting me, if you see it just get it. We have a product called BID for an Upgrade, which [00:19:00] essentially will allow you to upgrade automatically if we find an upgrade price that’s below the threshold in which you set.
We’ve seen a lot of positive feedback from our customers and we’re super excited about. Another thing that is coming very soon, and it’s in beta right now, is autopilot for hotels. If you’ve booked a hotel on a flexible rate and the price drops after you’ve booked.
Autopilot will rebook that exact reservation without changing the hotel, the property you’re at, the room, the rate details, and of course the cancellation policy so you can make sure that you are getting the lowest hotel rate between the time that you know that you have travel plans and the time that you actually take them.
Those are two products that we have. One of them is already out, the other is coming but things we’re really excited about nonetheless. Very good. And once again, that’s WithAutopilot.com/?partner=HurdyGurdy, [00:20:00] link in the show notes. Anything else about autopilot that you’d like to share?
The only other thing that I wanna share is that we love hearing from customers, whether it’s positive feedback, whether it’s negative feedback, whether it’s, Hey, I just saved money. We love hearing from you, so please don’t hesitate to reach out if you have any questions about autopilot, if you have any other comments or things that you think we should build, but we’re really excited about what we’re building and here to help make the post booking travel experience as good as possible for as many travelers as possible. Very good. And for listeners, feel free to comment on YouTube and you can also send email to me info@HurdyGurdyTravelPodcast.com.
And a little bit about you to close, any upcoming travel. We’re recording in March of 2026. Anything else for April or beyond? Yeah, I booked for April New York to [00:21:00] Taipei via Seattle on Delta One Suites, which I’m very excited about. I booked that using flash sale using SkyMiles. Very excited for the trip.
Staying hopefully at the Grand Hyatt in Taipei. Might get to Korea while I’m out there, but I’m not entirely sure and then hoping to fly the suite on ANA back to anywhere in the us I’m flexible and can reposition but I have about 85,000 Virgin Atlantic miles sitting in my account that I want to put to good use before they go away. I’m going to be flying Delta one again as well. It’s Hyatt Regency Taoyuan International Airport, April 6th through the eighth, and then flying to China Hyatt on the Bund Shanghai.
And then going on a cruise out of China. Oh, awesome. Any recent credit cards, new applications, credit cards you’re looking at to apply for soon? Ah, that’s a good question. I had an old [00:22:00] apartment where there was no fee to charge rent to a credit card.
I had a very nice heyday for a while where I was able to, essentially have unlimited capacity for spend. Me and a few roommates in New York, roommates were willing to Venmo me which was great. But now my building does charge a fee to use credit cards
so I don’t have that much capacity for spend anymore. But all that to say I am a lot eyeing the Alaska card the Atmos Summit card. I’ve done a lot of redemptions with Alaska recently, and honestly, I think if I did the accounting to look at how much I’ve spent in the partner award fee I might make up the annual fee right there on that card.
Very excited about hopefully getting that card soon. A big signup bonus. Many benefits on that card. I’m a big fan. I tried applying for that card twice. Got denied both times. Too many open accounts, too many recent inquiries oh no, I’m not sure if BOA is going to approve me, but I did open a business checking account with them, parked some funds for a bonus, so maybe [00:23:00] when I try again on or around July, I’ll have success.
Yeah. Awesome. Okay. Thanks for coming on today. Thanks so much Justin. Really appreciate it and again, if anybody wants to sign up for autopilot, you can go to WithAutopilot.com/?partner=HurdyGurdy, so really looking forward to seeing some people save money on their flights.
Very good. Thank you. And listeners will be happy to hear from you in the YouTube comments. Thanks everyone for listening and stay tuned for future episodes. For more content between shows, follow Hurdy Gurdy Travel Podcast on Facebook and x. Follow Justin Vacula on Instagram. Subscribe to Hurdy Gurdy Travel Podcast on YouTube for daily content, including travel videos, podcast clips and posts.
Find more information including episode transcripts at HurdyGurdyTravel.com. Search Hurdy Gurdy Travel on [00:24:00] SubscribeStar.com or become a channel member on YouTube to support my efforts starting at the $5 a month tip jar level. Receive special perks at higher levels, including private one-on-one conversations about card strategy, creative credit card spending, and asking podcast guests your questions.
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Travel at low cost with points and miles. Credit card rewards bring the smiles. Many adventures tales to be told, make and save money, the world will unfold.
Fight [00:25:00] the war on happiness. Pick up the gold. Hurdy Gurdy Travel Podcast breaks the mold.