After some initial setup, finding cheap domestic travel should never take you more than 15 minutes. If you still decide to outsource you travel arrangements, have your assistant try this path.

5 years ago we were fresh out of college, fresh into grad school, and pinching every penny. My time didn’t have the income potential that it does now. Those factors, combined with my incessant optimizing, made booking travel a nightmare. I would spend hours searching every possible combination of times and flights to try and save $20. I once remember asking my brother if he could come pick me up at an airport that was 6 hours away because it was $50 cheaper to fly there. Even when I found a good deal, I couldn’t pull the trigger, thinking “what if something cheaper shows up tomorrow?” If you need ideas on how to go insane, that should provide some inspiration.

Things are different now. I prefer to spend my time doing other things, and I’m working on satisficing for all but the most important aspects of my life. Here are the steps I now take when planning travel for within the U.S and Canada.

Why put something in writing when you can make a flowchart?

Flowchart for booking cheap travel

There are ways to save another $5 here and there (sites like sidestep and bookingbuddy will scour a billion sites), but based on my experience over the past 5 years, I think this gets close to the “minimum effective load.”

Notes and Resources

  • I fly Southwest whenever possible
    • super low fares
    • no fees for canceling a trip (HUGE)!
    • the most baby-friendly airline (in our experience)
  • Southwest DING! sends alerts for super-cheap fares to your desktop. I’ve flown Boston to Chicago for less than $50 each way (including taxes and fees)!
  • If and when you use Priceline (I recommend them for car rentals only), low-ball them. Last time I ignored the “you’re never going to get this price” screen and did in fact get my price.
  • Hotwire for hotels is a bit of a gamble. If where you stay is really important to you, only take high-star ratings, or simply skip Hotwire.
  • Set up Travelocity RSS feeds

Finally, if you’ve got a great tip, please share it in the comments.