By Brad Beckstrom
There are a ton of great travel hacking tools and adventure travel blogs out there. The blogs include lots of great tips like maximizing use of frequent flyer miles, credit card point programs, traveling during off-peak periods to less popular destinations and top 10 lists of great online tools and apps to use.
Despite the abundance of advice out there, one area that’s rarely mentioned is travel hacking for a family of four (or a small group of friends.) Planning for four or more people takes travel hacking to a whole new level. Keep reading if you’re traveling solo since these tools can also work when traveling alone or as a couple.
When planning for four people, you’re often not only dealing with the worst time of year to travel, like spring break or the holidays, but you’re also trying to use up some of your frequent flyer mileage. This goes against the grain of what most travel hackers recommend, including efficient use of frequent flyer miles and traveling at off-peak periods.
The airlines have done a pretty good job at making sure there are only a few seats available per flight for frequent flyers, especially during peak travel periods. The odds of you getting more than one of them at the time you want to travel with short layovers are pretty slim. To complicate this, the airlines have also added a premium ticket option which automatically doubles the number of points needed to magically make the unavailable frequent flyer seat available (FYI The seats are not premium just the dates of travel).
So, the goal for the family or group is to a) get the best fare possible b) get to the place we want to go (or at least close to it) and c) use some frequent flyer miles, credit card or hotel points when possible.
Airfares vary wildly by date. Use the best tools to outsmart the airlines.
Here are the tools and tactics I use to travel hack for a family of four.
First, consider what’s around you. Is there somewhere we can go that does not involve flying at all? Many families have discovered fantastic beaches, cities, national parks and small towns they never considered before. Secondly, National Parks and surrounding towns need our support. There are things you may not be able to show your kids someday, so do this first. Tripadvisor.com is a great place to go for ideas. Log in with your Facebook account to see where friends have been and get their recommendations. You can save any interesting locations including things you’d like to see, then pull them up in the app when you get there.
If your trip must involve international airfare, you should start searching the booking 6-8 months out if you want to do some effective travel hacking. If you don’t have that kind of time experts recommend six weeks as a sweet spot.
Think of the airfare as the outline of your trip. Once that’s established, you can color in all the details, get the tough stuff out of the way early and (comparatively) the rest is a breeze.
Since you’re starting months out, research more than one destination, some just won’t work out from an airfare perspective so choose a backup destination or two. In our case, I might start with Mexico but end up picking an alternative destination due to airfare. This is how we discovered the Dominican Republic a few years back. It’s really all about discovery and being flexible.
If your family that likes to travel during spring break or the holidays, the travel industry sees you coming. Think about some alternatives to those dates. Is it possible for your family to travel the first week after school gets out versus during spring break? Usually, that’s only an 8 to 10-week difference in the savings are significant if you’re traveling to Mexico or the Caribbean. All inclusive discounts can run up 50% starting in late May.
Start your airfare research using Kayak.com. Kayak is great for comparing prices but how do you know you’re actually getting a great price? Kayak has a price tracking tool in the upper left corner ( If you’re far out on dates I recommend watching the flights using this tool) As a comparison tool I often do a price check on Google Flights as well. For those who prefer a smartphone for searching, hopper and sky scanner have nice apps. All of these tools allow you to get price drop alerts, pick one or two and run with them.
If you’re looking to go someplace new and just want to explore all your options based on a date and a budget per ticket Kayak Explore is one of the best map-based tools out there. Just use the simple navigation for basic info and have fun with the map. You can even tune your trip selecting interests to filter locations like hiking, UNESCO sites etc.
- If you are open to new destinations and want to see deals I highly recommend an email newsletter like The Flight Deal or Scott’s Cheap Flights both have solid recommendations on great destinations with airfare deals. No need to sign up for the paid versions, both free email newsletters offer plenty of options and provide direct links to flight searches.
Once you found a couple of low-cost destinations in your time range, go to faredetective.com to get a more complete picture. Go directly to fare history and take a look at the one-year average history of airfares from your airport to the destination.
Using just kayak and fare detective I recently found four tickets to Puerto Vallarta, Mexico for $463 each, during a peak holiday period. In fare detective, I put in some basic information to see that tickets to this destination from our home airport rarely, if ever, dipped below $450 especially during holiday periods. They generally run between in the $700-$1200 range at those times. I could tell I had found a good deal on a good flight and could feel confident pulling the trigger. A week later the fares were up to $770. They may go down again but at least I felt confident I had not overpaid.
I did a quick check just prior to purchasing to see if possibly one of the tickets would be available with frequent flyer points. Delta had one seat available at a premium of 70,000 points. Pretty much what I expected for a holiday, even this far out. No thanks.
I quickly headed over to Chase Ultimate Rewards. where we’ve been earning over 4% on our credit card spending through a combination of Chase business cards and Chase Sapphire Reserve. In this case, I was able to quickly search for the matching flights in on Chase Ultimate Rewards which uses Expedia. With Chase, it’s important to search for your exact flight or hotel info rather than broad searches. I’ve had several occasions where a hotel or flight did not show up in the broader search until I put in more exact info about the airline or hotel name. Find your deal first then go to the credit card point site. If you don’t see it you can even call them and often they can find the specific flight.
In this case, I was able to find the exact flight with Chase and cover the full cost using ultimate rewards points. I’ve also used points transfers from Chase to airline partners like United, British Air, and Southwest to cover a portion of the travel costs versus straight points for tickets that are at a premium or limited availability. For example, if flights to Europe are on sale from JFK you could use some points to cover the first part of that journey then purchase your flights to JFK separately. Our flights to Spain last summer were $445 on FinnAir out of JFK from the DC area they would have been double that. We used some points for the hop to JFK.
I’ll admit trying to line up multiple plane tickets with these kinds of discounts can be tricky. However, if you’re using some of the best tools out there you can wrap it up in a few hours and even discover some new destinations.
Once you found your airfare hack now the fun starts.