35 Money-Saving, Point-Earning Travel Booking Hacks

Like most of those who find themselves regularly on the road, I’m obsessed with finding deals, discovering travel hacks and earning points. Over the years I’ve discovered a number of travel booking tips, secrets and tools that allow road warriors to stretch their dollars farther, like:

Flights

1. Book With Hidden City Ticketing On Skiplagged. Okay, so this is a controversial one. This site focuses on “hidden city ticketing,” which is essentially taking advantage of the fact airline ticket prices are driven more by the market than distance traveled. You essentially book further than where you really want to go, but disembark the plane early, to save money. Say I wanted to go from NYC to Denver. A hidden city ticket might be NYC -> Denver -> Phoenix, but I would get off in Denver and skip the section heading to Phoenix, because to book it this way was cheaper than booking the more precise NYC -> Denver flight. Keep in mind, if you miss a leg of your trip than the rest of the journey — aka your return flight — then typically gets cancelled, so book each leg as its own trip.

travel hacks

Photo: Google Flights

2. Use Google Flights As A One-Stop-Shop. There are so many benefits to using Google Flights over other booking engines. Along with browsing flights by outbound/inbound times and number of stops, I love that you can see a map view of a region to compare prices (ie “flights to South America”), with the ability to filter by airline, flight duration and budget. A fare calendar is another helpful tool allowing you to see exactly what days in a given time frame are cheapest to fly, as is a Tip bar that takes your search and shows less expensive but similar options. Once you find a flight you like, book it or save the itinerary to allow Google to monitor for price drops. Best of all, even though you’re on an aggregator platform it sends you to the airline’s website to book direct, meaning you won’t miss out on your frequent flyer miles and points.

3. Use The fare calendar on fly.comTypically when I’m about to book a flight I head over to fly.com to check their fare calendars. Like Google Flights, you can enter your route and approximate date to see exactly which dates are the best to fly for the best price. As I don’t like booking through online travel agents (OTAs) — due to the fact you almost always lose out on miles and points, not to mention if there’s an issue with your itinerary the airline is a lot less likely to help you or give you free upgrades and perks — I will then check which airline is offering the fare I want and head directly to their site to see if it’s the same. Keep in mind, if an OTA is offering a cheaper fare, whether for airlines or hotels, the airline or hotel will often price match (and potentially give you additional perks on top of it).

4. Set Up Fare Alerts On Airfarewatchdog. Do yourself a favor and head to Airfarewatchdog right now to sign up for their newsletter and flight alerts. If there’s a route you fly frequently or are looking to fly in the future you can sign up for fare alerts for that specific route (instead of getting general fare deals and hoping yours will be in their). I love the personalization of their offerings, as well as the advice given on their blog. I also follow on Twitter (@airfarewatchdog) to get real-time flight deal notifications, and have the free app to have access to the great features right on my phone.

travel hacks

Photo: AirHelp

5. Use AirHelp To Get Reimbursed For Flight Delays. Okay, so this hack is less focused on the actual booking, but is still part of the pre-trip experience. While rules vary by country, you can often be compensated for flight delays — a fact many fliers are unaware of. So how can you collect? My favorite tool is AirHelp, which does the work to get you compensated for your discomfort. If they get you money they keep 25% of the claim reimbursement; if they don’t get you money, you owe them nothing.

6. Know When To Book Using HopperWhat sets this website and app apart from other flight booking platforms is its attention to industry data and use of predictive pricing, telling you exactly when to book to get amazing deals. Search filters allow you to set a budget, number of stops and deals ranging from “Great–only the lowest fares” to “All–even overpriced.” Their “Ways to Save” tab gives insight into what a great deal for your route looks like, travel date comparisons and when to book.

7. Enjoy Price Alerts & Flexible Deals With SkyscannerAlong with fare alerts, the main reason I absolutely love Skyscanner is the option to enter your dates and location of origin and enter “Everywhere” as the destination. From there, you’ll be shown a list in descending order of where to fly on a budget and about how much it will cost. If you’re the adventurous traveler type it’s a great way to throw some spontaneity into your trip planning.

travel hacks

Photo: HitList

8. Explore & Save In A Quirky Way With HitlistHitlist offers a fun way to plan a trip, as you can search fun rotating categories for inspiration like SantaCon San Francisco, Weekend Getaways, Holiday Ski Weekend and Best of the Rest (best deals to unexpected places). See a trip you like and save it to your “Hitlist” (aka wish list) to be notified of when “good,” “great” and “spectacular” deals for these places can be booked.

9. Know When To Book Your Flight. According to Vice President and General Manager of fly.com, Warren Chang, Tuesdays and Wednesdays are typically the best days to search for flights because this is when airlines often release their sale fares. Moreover, Tuesdays, Wednesdays and Saturdays are normally the cheapest days to fly. Often flying on the actual holiday, rather than the day before or after, can lead to better prices and smaller crowds in the airport.

Katelyn O’Shaughnessy, CEO and founder of TripScope, also added in a Yahoo! Travel article that specifically Tuesdays after 3pm six weeks out is the “magic hour” when you’ll score the best deals for both flights and hotels. Moreover, booking after midnight means a large inventory with great rates.

travel hacks

Photo: Gabriel Ghnassia/Unsplash

Hotels

10. Switch Travel Dates To Avoid Cancellation Fees. Another great tip by O’Shaughnessy from the same article suggests that, if you’re past the penalty-free hotel cancellation booking window, change the date for the future. Then, call back to speak with a new person, and cancel. This tactic doesn’t always work, but it doesn’t hurt to try.

11. Get The Lowest Rate & Get Free Upgrades With TingoTingo, owned by TripAdvisor, is one of a few tools that re-book a confirmed, non-refundable hotel reservation for you as prices drop. You’ll have to browse their inventory for hotels so there aren’t unlimited options; however, there is a more than decent selection. One awesome feature of Tingo is free room upgrades, where they let you know when a room in a higher category becomes available for the same-or-lower price point of your current lower category room.

12. Get The Lowest Rate & Earn Rewards With DreamCheaperSimilar to Tingo in that it re-books your room to get the lowest rate, I like this platform because you can book your hotel on any website — meaning you can book direct with a hotel for added benefits like rewards points and a better chance at free upgrades and perks — and simply forward your booking confirmation to hotel@dreamcheaper.com to have the process begin. According to the startup they save travelers up to 60% on their bookings.

travel hacks

Photo: TripRebel

13. Get The Lowest Rate On Numerous Hotels With TripRebel. Like the two platforms above TripRebel re-books your hotel room until you have the lowest possible price using their own set network of hotels (the same as Tingo as they use the Expedia Affiliate Network to curate; again, not unlimited but great selection). The cool thing here is the ability to favorite hotels of interest to get notified of price drops at an array of properties — not just the one you booked — to get re-booked at any of them for the cheapest rate.

14. Use Your Social Media Skills For Discounts With Hotelied. This platform lets travelers connect their social media profiles to receive personalized discounts — also based on how long you typically stay in hotels, your professional connections and hotel rewards programs — of up to 50% off. Note that the site tends to list more upscale properties, so even with a discount it may not be cheap. Hey, it never hurts to check, especially if you’re a luxury traveler.

15. Bid On Hotel Rooms With Priceline. If you’re okay not knowing exactly where you’ll be staying when you book, hotel bidding sites like Priceline can be great for scoring a really, really good deal. Don’t worry too much about the mystery side of things, as the important factors — the star rating and the location — are disclosed before you hand over your credit cards digits.

travel hacks

Photo: HotelTonight

16. Download HotelTonight For Last-Minute Deals. Last-minute hotel booking apps like HotelTonight can save you a bundle if you’re flexible. They basically take unsold hotels up to a week out and offer them at a discounted rate. The closer to the stay date the better deals you’ll find. I love using HotelTonight while traveling and simply clicking my location and seeing a real-time map of what’s nearby with prices. Bonus Discount: Use my referral code “JFESTA4” when using HotelTonight and save $25!

17. Book With Aggregators With Loyalty Programs. Not everyone is loyal to one hotel brand, which is why aggregator sites like hotels.com and Expedia have huge inventories and give you points for booking with them. Hotels.com gives you a free night after booking 10 nights, while Expedia has Travel with Points, a free membership program where you earn points to potentially bring your booking down to $0.

18. Review Your Hotel On HotelConfidential.comIf you have a few minutes to spare, HotelConfidential.com gives $25 to travelers who create four 45-second videos showing the property in its true state. You can search here for hotel inventory or confirm the property is eligible by emailing info@hotelconfidential.com.

19. Leave A Note On Your Reservation Form. You know that box on your reservation form asking if you have additional notes that you typically skip over to click book? Next time, write something. If you’re looking for a room with a view or something special, ask for it. Often you’ll get these perks at no extra charge, or you can say something like “If it’s available when we check in I’d love a room with a beach view” or, if you feel awkward about outright asking for free perks, “Is there a way to get free Wi-Fi if I share something about the hotel on Twitter?”

This is also another instance where it pays to book direct. If a hotel sees you’ve booked directly with them rather than through an OTA/third party they’ll be much more likely to offer a free upgrade or amenity, whether you ask in the reservation form or at check in.

20. Become An Instagram Elite. In 2016 we’ll see a lot more hotels offering free Wi-Fi, if for nothing else than the free publicity it garners with selfie-obsessed, hashtag-loving Millennials who will likely take photos around the property and then share them on social media. Many hotels even offer rewards points, perks and free stays to Instagram sharers, especially those with a big following. For instance, you can earn Kimpton Karma points for sharing, while the 1888 Hotel in Sydney offers free stays to those with over 10,000 followers. These are just a few of numerous hotels taking part in this sort of initiative.

21. Score Airline Miles With Hotel Reservations Via Rocketmiles. Who doesn’t love earning free airline points on top of their hotel stay. Travelers can browse Rocketmiles’ selection of properties and see in the listing not only the hotel ratings, photos and information, but up to 5,000 miles per night (or more if there’s a special promotion; I’ve even seen enough for a free one-way domestic flight) through frequent flyer programs (and OpenTable) like JetBlue True Blue, HawaiianMiles, Alaska Airlines Mileage Plan, Southwest Rapid Rewards, Virgin America Elevate and more. Bonus Discount: Use this link and receive 1,000 bonus miles on your next booking.

travel hacks

Photo: Jetsetter

22. Become A Jetsetter Member. Jetsetter is free to join, and once you’re a member you’ll have access to hand-curated properties, often on the luxurious side, and daily deals averaging 20-30% off, though some are lower and higher, too. If you allow Jetsetter to connect with Facebook it will also personalize recommendations for you, although when you sign up it also asks you your travel preferences for this, as well. Bonus Discount: Click here to save 5% on your Jetsetter booking.

23. Tell The Hotel About Special Occasions. Having a birthday? An anniversary? A honeymoon? Let the hotel know beforehand, as they’ll often throw in some free perks to help you celebrate and up their customer satisfaction rating.

Both

24. Get In A Business Travel Mindset On Weekends. While business travel is often thought of as being more expensive than those of us slumming it in economy and staying in hostels, weekends often mean cheaper rates on business class flight tickets and business hotels, or hotels in a city’s financial district. Do some research. I’ve actually used flight aggregators to compare air tickets (I like fly.com for this) and have seen business class tickets on one airline cheaper than economy tickets for the same route and weekend dates on another.

25. Get Re-Booked For Budget Deals With YaptaLike Tingo, DreamCheaper and TripRebel this platform re-books your hotel room as the price dips…as well as your flights, and you’ll get an alert and a voucher for the difference. The other difference is it’s an actual travel agent doing the re-booking. It’s aimed at the everyday traveler as well as corporate travelers, with a tab for companies to make use of the site through. Keep in mind, airlines particularly have their own rules for issuing refunds. For example, while JetBlue offers travel credits that expire within one year, Hawaiian Airlines offers actual refunds.

travel hacks

Photo: Hipmunk

26. Have Fun & Save Money With HipmunkLet me tell you a sad tale that will make it clear why I will now always check this app. During the holiday season I wanted to visit a friend in Denver. I did a ton of research and used all of my usual hacks, but to no avail could I find anything under $460, on Delta, for the dates I needed. So I booked the overpriced ticket and silently vowed not to eat for the next month to make the money back. Then, a few days later, I was reviewing Hipmunk and saw almost the same flight on United for $260.

(*@#($*@#()*$!!!!!!!! :***(

That’s the keyboard version of how I felt, especially since Delta wouldn’t refund my ticket without a $200 change fee (which I feel they should have waived as I’m a frequent flyer with them and have their credit card, but that’s another story entirely).

Not only does Hipmunk have a great inventory, but it’s a really fun app that picks destinations for you based on interest (like Beach, Ski or Romantic), intuitively guesses your starting location, and allows you book hotels and flights based on filters like “Ecstasy” and “Agony” for the least pain-in-the-butt experiences. They also offer fare alerts, allow you to lock in airfares without booking for up to a week (for a small fee) and let you know what dates near to the ones you search are cheapest.

27. Join The Loyalty Program (And Actually Become Loyal). This is probably the easiest thing you can start doing today if you haven’t already. Do you have an airline you frequently fly or a go-to hotel brand? Join their free rewards program. There is literally not a single reason not to do this. It’s like not taking free money, as you earn extra points for hotels you’re already staying in and flights you’re already taking.

Before I even had the Delta credit card I was a SkyMiles member, and have flown first class for free based on frequent flier status and have enjoyed numerous free flights. Moreover, I joined Kimpton Karma and even on the bottom tier — aka just for joining before you spend any money — you get free Wi-Fi, a $10 minibar credit, a birthday offer, dining deals and the chance to earn free nights. You also earn points for taking part in fun on-property initiatives like their free wine hour and bike rentals. A bit unrelated, but for food I’m a fan of booking through OpenTable. Even if it’s a restaurant I know I don’t need a reservation for I’ll make one on OpenTable for the points.

These are just a few examples of thousands, maybe millions, of free programs that help you travel for free.

Better yet…

28. …Get A Co-Branded Credit Card. If you want to really maximize those points get the co-branded card for the brands you frequent. While there’s typically an annual fee it’s often waived the first year, and the perks and points outweigh the cost of the fee (though do the math to make sure it’s worth it for you). There’s also often sign up bonuses, which can be worth up to a week in accommodation or even a free flight if it’s big enough. Shop around and see where your awards will be maximized.

travel hacks

Photo: frankieleon/flickr

29. Get A Credit Card That Lets You Transfer Points. A universal travel credit card that lets you transfer points to hotels and flights is great for flexibility. A few to check out: Chase Sapphire Reserve Card  (here’s the credit card review; this is my personal favorite), Citi ThankYou® Premier and Amex EveryDaySM. There are also co-branded cards that do this well, like the Starwood Preferred Guest American Express, which allows travelers to use points at hotels in 100+ countries and with 30+ partner airlines. Moreover, transferring 20,000 Starpoints to parter airlines gives you a 25% bonus.

30. Download Flash Sale Apps Like Groupon And LivingSocial. When a business hosts a deal on Groupon and LivingSocial they’re typically coaxed to offer a discount of 50%+ (which I know because I almost offered a Groupon deal myself for my blogging services). If you check under their getaway tabs you’ll find hotel deals and often uber discounted package travel deals that include flights. Just make sure to read the fine print before booking for blackout dates and other stipulations.

31. Know About Best Rate Guarantee. If you’re like me and like to book direct, but sometimes see cheaper prices listed on OTAs, it’s helpful to know about airline and hotel Best Rate Guarantee policies. Especially with hotels, they’ll often not only match the price listed on the OTA to get you to book direct, but may provide further discounts and perks. For example, while Best Western matches the lower rate and provides a $100 Best Western gift card, Hyatt discounts the rate by 20% extra off.

32. Browse Like A Foreigner. While I’ve never tried this trick myself, I have plenty of travel friends who have, and have scored great deals. Try browsing under a different country page and currency and compare to what pops up when you search under your own home and currency, taking conversion rates into consideration. Also make sure if you do end up booking in another currency you use a credit card that doesn’t charge fees for this (for instance, I use the Capital One Venture Card).

33. Avoid Traveling During The Tourist Season. This may be obvious, but it’s worth reminding everyone of the benefits of booking flights and hotels during shoulder or off season to save money. Just because a place isn’t crawling with tourists during certain months doesn’t mean it isn’t worth going to. Do some research into what makes it off-season (and make sure the attractions and experiences of interest are open) and see if it’s worth it. You’ll likely end up loving the fact you’ve escaped the crowds and can have a more individual, personal trip.

34. Become A AAA Member. Not only is AAA amazing for car owners — run into any issue on the road and that paid membership will be well worth every penny — but you’ll notice when you book a flight or hotel there’s often a box to enter your AAA membership ID. Travelers typically save 5-10% on travel with this.

35. Delete Your Browser Cookies Or Switch Browsers. There’s a big debate in the travel community over whether doing this can actually save you money by showing you better prices. Why this is thought to work is that the cookies see how much you search a route — aka how in demand it is and how badly you want it — therefore increasing the price. Whether you believe it or not, it doesn’t hurt to try. Just ask Johnny Jet, who saved almost $200 by switching from Safari to Internet Explorer.

And to really reap the benefits of the above tips, check out this guide by Wanderinglustingk on maximizing your vacation days off

35 Money-Saving, Point-Earning Travel Booking Hacks (1)

Do you have any travel hacks relating to flight and hotel booking? Would love to hear in the comments below! 

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7 Comments

  1. Thank you so much for this information. I knew about some of these sites, but you just opened my eyes to a wider world of budget traveling. It was especially nice to read that its possible to be reimbursed for delayed flights, something I wish I had know years ago.

  2. I am planning an overseas trip this summer, so I went looking for travel hacks and I found your blog. This one has every information that I need; it is also very comprehensive. As a first time traveler to foreign countries, your write-up absolutely is heaven’s sent. Keep writing!

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