Since starting this website, the 2nd most popular question I get asked is “I want to go to [insert very specific place] on [insert very specific date]. Can you help me?” 

Unfortunately, I can’t help you how a typical travel agent would. (We specialize in finding trips so cheap you schedule your travels around them. Not the other way around.)

I do, however, have a few methods I use when I need to travel at specific times and don’t like what I find by simply searching the typical sites for my destination and dates of travel. In most cases, I end up finding 20% to 60% cheaper flights, so here you go:

  • Step 1: Go to Kayak.com & enter your desired airport & travel dates.  Assuming you don’t like the fares you find, proceed to step 2.
  • Step 2: Click the “change search” button and take as much advantage of “flexible search” as possible, and check all boxes you possibly can.
    • You’d be amazed at the number of times you can drop your airfare by 20%, 40% or even 60% by flying a day or two earlier, later, or going to a nearby airport & most flight search engines help you with that.
    • (I took my family on a cruise out of Miami and we saved over $650 by flying into Fort Lauderdale instead of Miami, and then taking a $20 Uber ride to Miami.

Kayak Flexible Search Feature

  • Step 3: If I’m more than 6 weeks out, I try to get an idea of what historical fares are from FareDetective.com and decide if I’m going to just sit and wait.  I sign up for updates on AirfareWatchdog & wait.
  • Step 4: Decision time:
    • If you’re within 3 or 4 days of your trip, click here instead of moving on.
    • If you’re less than 4 or 6 weeks away, but more than 3 or 4 days away from your trip, keep reading.
  • Step 5: If you’re still reading, you can’t really risk waiting because you’re in the window where fares are more likely to go up than down.  Now, it’s time to roll up your sleeves and get creative. I often use Kayak.com/explore and enter my home airport.  I quickly look to see if there are any other airfares that:
    1. Are not close enough that they’d be picked up as a nearby airport in “Step 2” above.
    2. Are cheap enough that I might be able to look into flying there, and then either booking a separate flight from there to my destination airport, or could hop on a train or rent a car.
  • Step 7: We’ve exhausted our “easy” options. Now it’s time to get really savvy with Priceline.com
    • First, you have to do your reseearch and make sure you’re comfortable with ALL of your flight options from City A to City B (including any redeye flights).  Whatever the case, the cheapest flights are the ones you’re likely going to end up on.
    • Assuming you’re comfortable with all of your options, make note of the lowest fare.
      • Now drop that price by about 30% and see if they take your bid. (They might!) If not, raise your bid incrementally until your offer gets accepted.
      • If you’re more than 3 or 4 days out, you won’t likely save more than 20% or 30% off the lowest available fare, but it’s worth a try if you really need to get on that plane.
  • Step 8: We’re starting to get desperate now, so hopefully one of the above methods have worked for you. This next step is called “The Deadhead approach” and has been around for ages.  (I owe this trick to my around-the-world traveling friend – Sean Orion.)  Now, go to Kayak.com/explore and enter your home airport.  Take a look at the map and see at what it costs to fly from your destination airport to other airports anywhere within a thousand miles of your destination airport.
    • If there are any fares that look cheaper, take a look at them and see start your search over and see if any of them lay-over THROUGH your destination airport. (Due to the way airline “hubs” work, you’d be surprised at the number of times it’s actually cheaper to fly longer distances than it is to fly shorter.)
    • If that’s the case, simply book your flight and get off the plane when it lays over in your layover city (which was really where you wanted to go).
    • Here’s the trick: If you use this method, you MUST book two separate one-way tickets.  Why? Because once you walk off the plane, they’ll cancel your return flight.  You also CAN’T check a bag because if you do, it will remain on the plane when you walk off & it will end up in the wrong city.
    • It’s rare that you find the right combination and it’s a lot of work, but when you do, it can be a big win.

Now do you see why I don’t have the bandwith to help you with such a search?  🙂  Good luck. I hope this helped!