Getting Creative

Video Time: 07:49

In this video, I’m going to talk about getting creative when redeeming miles/points. I’ll discuss free stopovers, free layovers, and free open-jaws. I’ll also talk about redeeming for business class and other creative ways to get maximum value from your hard-earned miles and points.

I’ll also explain below…


When you’re booking a flight with points, you can take a stopover on either direction of the trip. The stopover must be in one of the usual hubs that they use on route to your destination. These stopovers are free (except for slightly higher additional airport tax) and allow you to basically have two trips for the “price” of one. You will also need to pay the $30 agent fee for them to book the flight as stopovers can’t always be booked online.

To figure out which stopovers exist, you can either check online (such as Aeroplan when looking up your flights) or call an agent. Make sure to call at least twice as every agent seems to have various levels of knowledge. I’ll give you a couple examples of amazing stopovers that I have booked.

  • On route to Newfoundland from Alberta using points, I had the agent book me a stopover in Boston, Massachusetts. I didn’t even know this was a stopover but it worked and I had a one-week vacation in Boston before going to Newfoundland. Extra cost was around $50 in taxes.
  • On route to Mexico City, I got extra creative. It was during November and I wanted to see one of the parades in Chicago but I also wanted to see a friend in Austin, Texas. After a few phone calls, I was finally able to arrange a 23 hour and 57 minute layover in Chicago (not considered a stopover until 24 hours) and a four-day stopover in Houston, Texas where I rented a car and drove to Austin. Extra taxes were around $60. I was able to spend a saturday night in Chicago and see the beautiful downtown core plus I was able to visit my friend in Austin as well as the beautiful city of San Antonio for just $60!
  • On route to Calgary from Mexico City, I was able to book a stopover in Las Vegas for my parents. This was a tricky one since it’s not a normal hub. However, they managed to put them through to Houston and then onto Las Vegas for their three-night stopover. Again, extra taxes were just $50 because of the additional airport landing.

All in all, stopovers are an amazing way to see two places for nearly the price of one. If you’re going to Africa, you can book a stopover in Europe. If you’re going to the South Pacific, you can stopover in Hawaii. In addition, a stopover can be up to 1 year in length!

Let’s not forget about open-jaws either!

An open-jaw means that you fly into one city and out of a different city. This gives you a chance to include land-travel into your itinerary and really opens the doors to adventure.

Here is an example of an amazing open-jaw I booked, along with a stopover and layover on route to South America.

  • My wife and I were about to get married in Mexico but I didn’t want to book a regular return-flight. I wanted to squeeze all the value I could out of the points. Instead, I booked a flight to Cartagena, Colombia with a six-week stopover in Mexico. Then from Colombia, I booked an open-jaw, which meant we would actually fly back from Bolivia three months later. WOW! We were able to backpack through Colombia, Ecuador, Peru and Bolivia on land. Then, just for kicks, I booked a 23-hour layover in Mexico City on the way home to say hello to my family-in-law!

This is just one example of getting creative with award bookings.

In general, all long-haul flights come with one stopover. International flights (basically anything outside of Canada/USA) come with one stopover and one open-jaw OR two stopovers. If you were to fly to Australia, you can practically fly around the world, stopping in three different continents for the price of one!

Layovers can be fun too!

A layover is anything less than 24 hours. Once it reaches 24 hours, it is now considered a stopover. Traditionally, layovers get a bad rap because it’s usually in a city you don’t want to be in for just a few hours, which means you can’t even leave the airport. But imagine actually asking for a layover! That’s what I do. Let’s say your flying to Mexico and you’re having a stopover in Costa Rica. You could also add a 23-hour layover in cities such as San Francisco, Los Angeles, Chicago or sometimes even New York. If you’re flying to Europe, you could maybe add a 23-hour layover in Paris, Madrid or London. The possibilities are endless and flying into a city just to enjoy a night-out will make you feel like a rock star!