Bolivia to Chile

Sometimes you have to make your own path…

Why do some people always seem to travel for cheap and others search in vain for deals that elude them? Often it comes down to a combination of patience, persistence, and creativity. As creative thinking author Roger Von Oech advised, often you need to find “the second right answer.”

Next week I’m traveling from Mexico to South Carolina on a Delta frequent flier ticket. Their miles are often derisively referred to as “Skypesos” because they’re so hard to cash in compared to most other airlines. Getting the lowest level awards are next to impossible. But…this is the fourth time I’ve flown Delta for free, so it’s close to impossible, not completely so.

I managed this, as I’ve done the other times, by basing my travel dates on when Delta had availability, not when it was most convenient for me. I’ll make all kinds of changes in my travel schedule if it’s the difference in paying $50 in cash-in fees or $550 to buy a ticket.

Over the past few years, due to some smart travel hacking efforts, I’ve flown for free (except for taxes and fees) to four continents, plus a few domestic flights. Rarely was this as simple as punching in my dates and hitting the booking button. Here are a few contortions that were required to cash in all those miles for almost-free tickets:

  • I flew American to Bolivia and LAN back from Chile because neither had openings both ways.
  • I started and ended my four-country tour of Eastern Europe not in Sofia, as I’d planned, but in Budapest because that’s where I could get a mileage ticket flight the time of year I wanted.
  • My family returned from Southeast Asia on a different airline than me.
  • My daughter and I moved to Guanajuato a week earlier than my wife because we were paying and she was using mileage.
  • I got an extra cheap hotel room one night in Salt Lake City because the date I wanted to fly out on mileage wasn’t available. The next day was.

Be a Travel Deals Detective

This kind of willingness to be flexible also applies when you’re paying. I recently got quoted in this Reuters article about flying an unaccompanied minor because they liked my story about how I avoided paying United Airlines $300 to put my daughter in a seat by herself. I accompanied her up and back on Allegiant, then she returned on JetBlue. It took some time and a calculator to figure all that out, but we saved a a few hundred bucks and it all went smoothly. creative travel savings

Hotels? Go beyond the typical booking engines everyone uses. For normal hotel deals, try Trivago.com and get a look at what everyone is charging. If you just need a chain hotel in a certain area, use Hotwire or Priceline bidding. Try the HotelTonight app if it’s last-minute.

If all else fails, use none of them and go old school, researching independent options that don’t want to pay the big booking sites. Look at guidebooks, destination websites, and the third page of TripAdvisor for hidden gems. Ask friends of friends. Or if you’re staying a while, rent a home or apartment.

If you’re coming up empty finding a reasonably priced way to get from A to B, make sure you’re looking at all the options. From Megabus to Amtrak, Easyjet to AirAsia, one-way rental cars to alternate airports, there multiple possibilities to try before giving up.

Travel is so much easier than it was when I started 20 years ago, but it’s also easier than ever to overspend. It’s easier to mistake info that pops up in your first search as the final word. Really, it’s just a starting point. Dig deeper and wider to find a better answer.