Half a decade as a Director at Asia’s largest online travel agency taught me the travel industry’s dirtiest secret: people pay dramatically different prices for the exact same hotel room or the exact same seat on a plane. This phenomenon, known as differential pricing, applies to all online purchases – smart travellers save money, everyone else gets overcharged. This guide reveals the key mechanics of online pricing, along with every trick in the book to help you game the system, and ensure you get the cheapest online booking price every time.
1. When to Book
As with comedy, when it comes to getting the best prices online, timing is everything.
CHEAT SHEET
BOOK on Sundays 3-12 weeks in advance
TRAVEL Thursdays and Saturdays, August is cheapest
Take advantage of discount sales events
What the Data Tells Us
Expedia’s 2025 Air Hacks guide provides data-driven insights into the best times to book flights. I’ve pulled the most relevant bits below – thanks Expedia!
Discount Sales Events
If you have the patience to wait and plan ahead, taking advantage of promotional campaigns is a great way to score some of the lowest booking prices you’re likely to find.
Major online sales campaigns
Black Friday (Nov), Cyber Monday (Dec)
Double-digit Sales (ex. 8.8, 11.11. 12.12)
Seasonal promotions
Typically Spring, and end of Summer
Xmas, Easter, Valentine’s day etc.
Always look out for sales
Flash sales, coupons, discount codes in promotional emails
The point can certainly be made that not all sales are created equal. Many promotional campaigns are more about generating buzz than actually providing earth-shatteringly low prices. That’s why I recommend checking the comprehensive list of “real deal” airline sales at Jack’s Flight Club to learn which sales campaigns are worth waiting for.
2. Where to Book
The online travel booking market is a noisy space and it’s easy to get overwhelmed by the sheer number of options out there. Fortunately, I’ve scoured them all and put together a short list of the best places to get flights and hotels. If you’re hungry for more, check out my complete list of travel resources here.
CHEAT SHEET
For flights: Skyscanner | Google Flights
For accommodations: Booking.com | Trip.com
Always check across multiple platforms to find that elusive deal
Use aggregators to find what you want; then check the price from the local provider
Best Places to Book Flights
Bob’s Top Choice
Skyscanner
This is my go-to place to find flight deals. Wide search across many smaller platforms, and the calendar view is clean.
As much as we all crave silver bullet solutions, ultimately it pays to cast a wide net.
Always check at least 2 sites before booking to increase the chances of finding that elusive deal.
Check the source
Aggregators are platforms that search across multiple websites and display the results in one place. Popular examples include TripAdvisor, Viator, and GetYourGuide.
They’re great for finding what you’re looking for but they charge the individual suppliers a 10-20% commission for exposure, which inflates the price you pay.
This is especially true for tour companies, which tend to be relatively small and operate locally, so they rely on global aggregators to reach potential clients.
To get the cheapest online booking price, find the tour you want on the aggregator, and then make the booking on the local tour provider’s website for big savings.
3. What to Book
Now that we’ve covered the when and where appetizers, let’s move on to the the main course: what bookings tend to provide the best value? In this section, I’ll use side-by-side screenshots of real online booking results from well-known travel sites to show how to get the cheapest online booking price by making smart choices.
CHEAT SHEET
Prioritise barebones rates for the cheapest “no frills” variant of any booking
Multiple single tickets are often much cheaper than one group booking
When traveling one-way, check if the equivalent roundtrip flight is cheaper
Avoid Bundles – they offer limited discounts (if any) and aren’t worth the headaches
Barebones Rates
The “no bells and whistles” version of any booking ex. for a hotel: breakfast not included, no cancellation, no early check-in/late check-out etc. – just the room
We see a significant price difference for the same room at the same hotel on the same dates.
There are 3 differences between the standard booking and the barebones booking:
max occupancy (2 vs. 1)
cancellation policy (can cancel up to a date vs. non-refundable)
payment terms (pay later vs. pay now)
If you can live without these benefits, you’ll save 19% on your booking.
The Upside
Effortless savings just by choosing the cheapest option.
Avoid paying for things you don’t want ex. you prefer to skip breakfast or eat outside the hotel.
The Downside
Extras like breakfast included, early check-in etc. may well be things you value. If you do want them, it is usually cheaper to get extras “included” in your room rate rather than paying for it at the hotel.
Verdict
Make sure you know what you’re paying for. If your goal is to get the cheapest rate, book hotels that have barebones rates. Otherwise be sure to only include the extras you actually want in your booking.
Multiple Single Tickets (Are Cheaper Than Group Bookings)
1 booking per passenger vs. 1 booking for a group of passengers ex. 5 separate bookings for 5 passengers, as opposed to 1 group booking for say 5 family members
We see in this example that there are 4 seats left at £777. If I try to buy 5 seats in a single booking, the airline will assign the higher price of £1,391to ALL 5 tickets, not just the 5th ticket!
To make it worse, the 2 premium economy seats left at £1,172 (still cheaper than £1,391) aren’t even bookable with the group booking.
The result? The airline overcharges me by a whopping 54.6%! (savings of ~£2500)
The Upside
Huge savings, especially for larger groups (I ran another booking example for 7 passengers with 6 cheaper seats that yielded even bigger savings).
The Downside
It’s more time-consuming and tedious to redo the same booking more than once.
Final Verdict
When booking for a group, it’s quick and easy to check the price for 1 passenger. If there’s a big difference in price, doing multiple bookings is well worth the effort.
Note you can do agroup booking at the lower price, and another group booking at the higher price, which is less annoying than booking only single tickets.
Roundtrips (Can Be A Cheaper Way To Book A One-Way Flight)
A flight to and from a destination vs.A flight to the destination without the return ex. When booking a one-way ticket, it is sometimes cheaper to book a round trip and just skip the return flight.
You can see here that the same flight from London to Dakar is much cheaper if you also add on a return flight.
This is completely illogical. Buying x+y should not be 20+% cheaper than just buying x.
In an effort to increase the occupancy of their planes and expand their revenue per booking, airlines often incentivize customers to buy the return flight for less than 2 one-way tickets. As a result, in some cases, this leads to silly pricing, where just one of the legs becomes more expensive than the roundtrip.
The Upside
Huge potential savings, 20+% savings is nothing to sneeze at.
The Downside
It’s an extra step to check whether the roundtrip fare is lower than just the one-way.
Final Verdict
When booking a one-way ticket, always do a quick check to see if the roundtrip is cheaper. If so, simply book the roundtrip and don’t fly the second leg of the trip.
Bundles (are bad)
A “package” deal containing 2 or more products in one booking ex. hotel + flight
The actual savings received from bundles are wildly exaggerated. Most of the discounts you receive apply whether you bundle or not.
The above example claims bundle savings of 24%, in reality it’s 3.3%. In other tests I ran, the price was identical to booking separately.
The Upside
One-stop shop, no need to go through the booking/payment process twice.
The Downside
Bundle savings are too small to matter.
Bundles often carry restrictions on which flight and hotel you get to pick, resulting in inconvenient flight timings and limited hotel choices.
You may think booking everything in one place means it’ll be easier to deal with just one point of contact. Sadly, you run the risk of poor customer service should you need support on one part of your bundle.
If for example you book a flight+hotel bundle and something goes wrong with the flight, the airline and bundle provider will often try to pass responsibility off to each other when you call.
Many bundle portals don’t allow you to lock in your personal details during booking. You can’t input your miles info, seating preferences, emergency contact info etc. and have to do all that on the app or at the airport.
Verdict
Avoid travel bundles, they’re a false economy where the meagre savings you may get aren’t worth the headaches that come with them.
4. How to Book
Finally I’ll share some pro moves I learned working in the travel industry to unlock the cheapest online booking price. Again, I’ll compare side-by-side screenshots of online booking results to show how to get the best price. Use these every time you book and good things will happen.
CHEAT SHEET
Log in for up to 10% off
Book on the mobile app for an additional discount
Build your loyalty status to get special rates, earn points/miles, and receive rewards
VPN through another country to access cheaper foreign rates
Log In
Create an account with the website and log in before you book. i.e. When you don’t log in, you’ll be treated as a “guest”.
Just by logging in you get an extra 7.2% discount (up to 10% in other tests). It’s that simple.
The Upside
Logging in automatically applies savings.
The website will remember your details so you don’t have to type them in.
Your account will keep track of your current/past bookings for easy access.
You only receive loyalty points/miles/credits when you are logged in.
The Downside
The first time you book, signing up is an extra step.
There are often promotional emails sent to the email you used to log in which may be unwelcome. Most websites provide an “opt out” box to uncheck, or you can just unsubscribe.
Final Verdict
Always log in, it’s free money and you get lots of other benefits too.
Book on the Mobile App
Download the app on your phone and use it to make your booking. i.e. That means not booking through a web browser on your computer or an internet page on your phone.
Simply by booking through the phone app you get 10% off compared to booking on your computer.
The Upside
Using the app automatically gets you double-digit savings.
App bookings tend to integrate better with your phone, so you can receive notifications for example.
The Downside
Some people may prefer booking on a computer with a larger screen, easier navigation with a full-size keyboard and mouse, and a more familiar interface.
Final Verdict
Book with the app. It’s easy money and in a world where constant phone-use is becoming the new normal, the app is getting more love in terms of functionality investment.
Note, based on my testing, app discounts are more frequent when booking hotel stays.
Build Your Loyalty Status
Many sites have a loyalty program that you can sign up for which gives you access to exclusive deals. You can also earn rewards as you complete more bookings. ex. Airlines provide discounted rates to their higher tier members, plus miles you can spend on flights/upgrades.
Because of my loyalty status on Agoda as a VIP Platinum member (earned by making 10 bookings in a year), I have access to a 7.1% cheaper rate for the same room on the same dates (max is 20%).
The Upside
Access to discounted deals that are not made available to non-loyalty members.
Accumulate points and miles with every purchase to spend on future bookings, upgrades, or travel perks.
Rewards often go beyond this with prioritised check-in/boarding at the airport, access to lounges, free upgrades, complimentary gifts etc.
Loyalty members typically get dedicated support channels for better customer service.
The Downside
Loyalty status has to be maintained, it’s rarely permanent. Making lots of bookings to unlock discounts can feel a bit like a false economy.
You may face dilemmas about booking on your loyalty site vs. booking somewhere else that happens to have a better price.
Final Verdict
Building your loyalty status is definitely worth it, but you need to be smart about maintaining it and claiming all the benefits.
A good practice is to stick with one travel platform you like and build your loyalty there rather than spreading your bookings around. This generally leads to deeper discounts and better rewards.
VPN Through Another Country
A Virtual Private Network (VPN) masks your identity by connecting your computer to a remote server. i.e. A VPN can make it seem like your computer is in a different location when online (=geo-spoofing).
For those unfamiliar with VPN, if this sounds a bit complicated to you, don’t worry – it’s not. You download a VPN like any other program, and click on/off like a light switch. It’s that simple.
Skyscanner sets the price based in part on my IP address which tells it my location.
By using a VPN, I’m changing my virtual location to France, and getting access to a 4% cheaper rate only available to French consumers.
The Upside
The best rates are often geo-specific, so VPN gives you access to a world of savings.
The Downside
The free version of a VPN limits which servers you can connect to. For best results, you’ll want to pay for a premium VPN. Spending money to try to save money may feel counterintuitive.
It can be time-consuming to hunt for discounts by going through the booking process for different geographies. It may not be clear which location will give the best price.
The laws surrounding geo-spoofing vary by country. Generally using VPN for personal security or to access content is legal, but it’s essential to abide by any official restrictions.
Final Verdict
Using a VPN can save you money, but it requires some bargain hunting.
The discount is highly dependent on the route you are booking. Generally, China, India, Indonesia, and Türkiye are good VPN location options for deeper discounts.
Important note, it is your responsibility to review the relevant regulations surrounding VPN use in your country. Be sure to check the terms of service of the website you are visiting.
I’ve included below a handy list of the best VPN services out there. If you’re looking for more useful lists, follow the link for a collection of all my recommended travel resources.
Bob’s Top Choice
Windscribe
I’m a long-time user, Windscribe offers the most generous free VPN plan I’ve found. Easy to use, does the job, no fuss.
Still hungry for more savings? Fear not, below are a few more tasty nuggets of money-saving wisdom to help you get the cheapest online booking price.
CHEAT SHEET
Get a travel credit card and reap the rewards
Sign up to email alerts to be notified about price drops
Install the Honey browser extension to automatically apply discount codes
Travel Credit Cards
Marketed as a sexy lifestyle enhancer, the travel credit card has become immensely popular. You get to enjoy huge welcome bonuses, spend points/miles instead of your hard-earned cash, receive complimentary travel insurance coverage, and reap rewards in the form of perks like free checked baggage and airport lounge access. I’ve included below the top travel credit cards I recommend, but if you want access to all my travel recommendations, check out all the best travel resources here.
Bob’s Top Choice
Capital One VentureOne Rewards Credit Card
My fave card for flexible points redemption. No annual fee, get miles for all purchases, not just travel, and a big sign-up bonus.
It’s a free extension for your web browser that automatically looks for discounts whenever you’re booking online.
The example on the right is from the Paramount+ site and auto-applies 9% off (the deal may no longer be valid at time of reading).
Set and forget, it’s free money.
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That’s it folks! Well done to those of you who read this far, and thanks for your support 🙂 My fervent hope is that these tips help you find the cheapest booking price online, spend less on flights and hotels, and leave you with more money to enjoy your destination to its fullest.
Please feel free to leave comments, feedback is always welcome, and if you have any questions, email me and I will answer post-haste. Cheers!
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