If you're anything like me, nothing is more satisfying than scoring a cheap flight or hotel to somewhere you've never been (or can't wait to go back to). And since travelers do most of their shopping online these days, there is no better time to keep your eyes peeled than on Cyber Monday, right? Yes and no...

If you are flexible, and quick to pull the trigger, you can find the deal of a lifetime. One misstep or hesitation, however, and you'll find yourself frustrated that you even tried. I've experienced both.

After years of trial and error, occasional indecision, and reading countless articles on where to look and when, I figured now would be a good time to offer you a machete- to cut through all the "internet brush" out there. Before I put the machete in your hand, however, take these tips on how best to use it...

 

Warnings & Tips

 

1. Expedia, Orbitz, and Travelocity are all the same freaking company.

What does this mean for us? It means, don't bother wasting your time switching from one to the other to find a better deal on the flight itself. The price is going to be more or less the same. Even the user interface is essentially the same. The only reason you might hop between these is if all coupons have been claimed for one of the companies when you go to book (i.e. you weren't fast enough) and you settle for a lesser coupon still available with one of the others. 

 

2. Priceline and Kayak? Same company

See above. 

 

3. All of those "cheap flight-finder" companies are using the same flight-search software. 

Most of these online "flight-search engines" are more like engine-readers than engines. Most of them are using Google's ITA Flight Matrix Software, then pushing it through their algorithms and interfaces to to give you their version of the same deal.

Again- what does it mean for us? It means that most flight finders are going to produce more or less the same results, and you shouldn't spend too much time going through all them like I do (haha), unless you're determined to find anomalies like I am (sinister chuckle). 

It's important to note that some airlines don't even make their fares available to the search engines, and therefore good deals sometimes go unnoticed. You're better off figuring out who flies to wherever it is you want to go, and searching their website directly for any promotions. You could also try Googling for promo codes that might apply to the fare- this rarely works for me, but every once in a while, I get lucky. 

Whenever possible, when it comes to travel bookings, I usually suggest going through the company's website directly- particularly with flights. On multiple occasions, I took advantage of a cheap fare that I found through a travel company, only to find out that I was shit out of luck when it became necessary to make adjustments to my flight details. Should you need to change a flight, booking with the carrier is often one awesome flight attendant away from a problem solved, otherwise it's going to cost you big time unless you purchased the travel company's travel insurance. Which brings me to my next tip...

 

4. Don't buy travel insurance! Er.. check to see if your credit card offers travel insurance!

I was psyched to learn one day when I was bored, online, reading the details of my credit card's features (who does that?), and discovered that as long as I booked my travels with that card, I didn't need to purchase travel insurance with the booking agent! This probably saves me several hundred dollars a year (i.e. a free flight). 

If your credit card doesn't provide you with travel insurance, I suggest getting one that does! In addition to those savings, most of them don't charge you foreign transaction fees (more savings), and offer you with great travel rewards. Yes, please!

If you don't have or want these features, stop reading my blog; you're unteachable. Just kidding- buy travel insurance.

 

5. A "deal" is not necessarily a deal. 

Think "As Seen On TV" merch. Or any infomercial. Many "deals" and "sales" these days- even Black Friday/Cyber Monday ones are just a marketing gimmick. Certainly not all of them- but many.

I saw several companies this year offering deals of 30-40% off regularly priced fares, which somehow came out to around the same price that I would normally consider a pretty good deal, but probably wouldn't spend more on. That's why it's important to know what a good deal actually is so you don't get duped by these marketing tactics. Bringing me to my next two tips, which I'm going to group together...

 

6. Do your research on what a deal actually is in regard to what you're looking for, because you don't have time to do it on the spot.

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7. If you do find what you consider to be good deal, be logged in already, and book immediately.

To illustrate why these are important, I'm going to explain what happened to me once when I was looking for a Black Friday deal on a hotel in Mexico...

Knowing that Expedia.com has some pretty ridiculous Black Friday/Cyber Monday deals (up to 90% off), I fired up my laptop and opened the website, had my phone out with the Expedia app open, sipped on a coffee to keep me sharp, and refreshed every couple of seconds leading up to 9:00 a.m. PST sharp. I felt like I was ready, and figured I'd know a good deal when I saw it. After all, I've been doing this a while. 

The moment it was 9:00 a.m., I refreshed both screens and started plugging away. I saw a lot of hotels that were 30% off, 50% off, some as high as 70% off. But I knew that really meant off the list pricing, which nobody would ever pay ever, and so I was trying to figure out where the true deals really were. 

I saw a couple potential deals that I might be okay with purchasing, but just to be sure I wasn't getting bamboozled, I was cross-checking these prices with other sites, which of course, all miraculously offered the same exact "exclusive" Black Friday deal. It wasn't until a refreshed a couple times more that I realized they were offering Promo Codes to bring these fares down even further, yet they were neatly hidden at the bottom of the page, and somehow didn't appear exactly at 9:00 a.m. like I assumed they would, which threw me off. 

Realizing I could take away another 75% off the fare I was already okay with paying, I hurriedly went back to the booking screen and typed in the Promo Code, which dropped an already discounted fare of $404 down to about $165 (the list price for three nights would have been around $1,000). It was a miracle that the coupon was still available in my mind, being that 15 minutes had already passed. That's when I temporarily became an idiot. 

With a deal like that, I thought, I could really get a steal on something even better. I spent about two or three minutes in another tab, before I decided to stick with what I had. I went to check out, when Expedia refreshed my page- AND MY FARE!

"THIS COUPON HAS EXPIRED."

This can't be! In those two or three minutes of indecision, I lost my opportunity for a steal of a deal in a legitimate 4-star hotel. Frustrated, I went back to the main page for the next best coupon available- 50% off. 

I entered in the new Promo Code and proceeded to check out, at which point Expedia reminded me that if I logged in, that I could earn rewards points. I rarely turn down those things even though I hardly use them, and decided to sign in. I took a screenshot of the discounted fare, just in case. 

Sure enough- Expedia refreshed my page, and my fare, once again. 

"THIS COUPON HAS EXPIRED."

You've got to be fucking kidding me. 

"PLEASE REFRESH TO TRY AGAIN OR CALL CUSTOMER SUPPORT."

Refresh.

"THIS COUPON HAS EXPIRED."

I dialed customer support immediately, and to keep this part short...

  1. I ended up talking to four different representatives whose native language was clearly not English (no offense) for over an hour during a critical purchasing time.
  2. I was disconnected halfway through.
  3. I had to explain the same exact story over again to all four hard-to-understand reps. 
  4. I informed them I had a screenshot of the fare that was offered to me.
  5. I fruitlessly attempted to reason with a large, outsourced corporation via logic and common sense, reminding them that a couple hundred dollars to their large company was nothing to them but everything to me, and that I was a Travel Writer with a decent following who could a) write a fantastic story about how Expedia was great and saved my ass or b) add to the long list of articles about how much they now suck because they are no different than any other large corporation who doesn't give a shit about anything but the bottom line and employing reps whose flexibility is limited to the instructions given to them on the computer screen. 

Fail. The only result of those efforts were a lesson learned. I had no one to blame but myself, because I should have taken advantage of the deal the moment I realized I was lucky to have it in the first place. Instead, I found myself cursing Expedia. 

The one salvaging bit I managed though, to reference Tip #1, was having the savvy to realize Expedia's "partner" companies might have a different version of the same deal hanging around. So, I picked my head up and surfed over to Travelocity.com, where I ended up getting lucky for a still-active coupon that gave me about 33% off, which meant I paid around $300 in the end. Meh.

Learn from my mistakes!

 

How To Be Ready This Cyber Monday

 

If you've made it this far down, then you're already off to a pretty good start. But you can do yourself one better by getting familiar with a couple of sites who are really good with a machete, and have cut down most of the brush out there for us. It really depends on what you're looking for.

 

If you're looking for Flights...

One of my favorites is TheFlightDeal.com. They're an incredibly useful and informative resource- particularly in regard to flying. They have articles teaching you how to use the ITA Matrix Software, and they constantly post great finds as well as how to maximize them. If there is a good deal to be had in the air, they're likely onto it and will tell you how to secure it. They've also compiled "A List of Black Friday / Cyber Monday Air Fare Sales" which illustrates Tip #5 above. 

Another great resource is SecretFlying.com. They're constantly scouring too, so they're always finding and posting great deals as well as error fares. Also, TravelPirates.com is pretty good and in the same category. 

Another thing you can (and should) always do is to set Fare Alerts with a website like AirFareWatchdog.com or the Hopper app on your phone. If there is a place you want to see or return to, these free services will be sure you don't miss out when fares are cheap.

Finally, check in with the airlines' websites directly on Cyber Monday in the morning. As stressed above, you're almost always better off booking directly. Just don't forget to check the fares ahead of time so you know how much of a "deal" you're getting!

 

If you're looking for Hotels, Car Rentals, and Travel Packages...

Refer to the list makers! And get your credit cards ready. Websites like Conde Nast Traveler, Travel and Leisure, Huffington Post, Forbes, Thrillist, and other major news resources for updated lists on the deals that are going around. Pick the ones that you really want to take advantage of, and be ready the second it kicks off.

Sites like Expedia.com (grrrr) and Hotels.com will be having huge sales as they always do, but be sure to head my advice above to really prepare yourself. Don't forget- the real work comes on Sunday! Make sure you do your research for reference, and then show up on Monday morning prepared. Personally, my goal is to conquer Expedia. 

As Cyber Monday continues to develop, more and more people are figuring out how to be ready for it. Which means more competition for us how are trying to snag a good deal. It all comes down to being prepared! 

One final tip: if you're up on social media, many of the big cats like to post their Cyber Monday deals through platforms like Twitter and Facebook. So be sure to check out your favorites first thing in the morning. 

Got a few tips of your own? Share below!

Happy Traveling!