Booking Airfare & Flying…..with Kids! (Part 2 of 3)

Booking Airfare & Flying…..with Kids! (Part 2 of 4)

I know exactly what you’re thinking….what the heck took them so long to post the next part of this series!  Haha!  For all those who actually are interested you can wait no more!  In this post I will focus on the optimal ways for you to book your airfare when traveling with kids.

First things first….Patience!!  I realize traveling with kids is easier said than done.  I promise you, more times than not your patience will be rewarded.  

Just an Overview

I travel a lot for work.  Often times though, the carrier I fly is not within my control.  However, for our personal travel we have flown to places like Hawaii, Boston, Chicago, Buffalo, Washington D.C., Denver, Vancouver, Anchorage, Calgary, and Austin.  From those trips I have sorta developed a system.  To some of you it may not make a bit of sense.  However, I promise there is a reason for the madness.

Time of day to Fly

Here’s the lowdown on what type of flights typically make up the cheapest airfare.

  1. Overnight Flights
  2. Flights with multiple stops
  3. Red-eye departures

We have flown (and Drove) overnight with our kids quite a few times.  I only recommend choosing the overnight flight if you are truly flying across country or further and non-stop.  Kids don’t react well if they are awoken from a deep sleep.  In addition, it takes them several days to recuperate, so keep that in mind.  It is also much easier if you are flying from the West Coast to the East Coast due to the time change.  It just makes it easier to get back on schedule if you are able to get the right flight.

Making Stops

Most people hate flying and making stops.  When we don’t travel overnight, we actually prefer flights with 1 stop.  For example, in a few weeks we are flying to Vancouver by way of Toronto.  If it were non-stop it would be an almost 8 hour flight.  Flying overnight wasn’t going to work out, so instead we are splitting it up, almost 3 hours to Toronto and almost 4.5 hours to Vancouver.  The flight to Vancouver, though long puts us just past the point of no return with kids on an airplane.  If they don’t fall asleep it could be a long flight haha.  However, our 1 way flight to Vancouver from Orlando was only $130 per person.  You read that right….$130 per person, and yes I booked a one way ticket.  The price was too good to be true.  We will be flying WestJet, which is a first for us, so it should be interesting.  WestJet is a Canadian carrier that is like a Frontier or Spirit from the United States.  I will say my first encounter with their customer service has been a positive one.  They changed our flight times without really telling us and so when I called to ask about it and get some clarification, they went ahead and gave us reserved seats near the front of the plane for free.  To some that seems small, but on a no frills pay for everything air carrier, you take what you can, especially so you can be near the front of the plane (faster to get off), and all next to each other.

Our return trip is with American Airlines.  I have long boycotted American Airlines.  I will save that story for another post.  It will make you never want to fly them again.  I try at all costs to avoid flying them for work too.  The one time I couldn’t avoid it I had pretty major issues.  However, just like the flight to Vancouver, our flight home was just too good to be true as well being $126 one way with a single stop in Phoenix. So that’s $260 roundtrip to fly across all of the United States from Orlando, Florida to Vancouver, BC.  That’s almost unheard of.

The Tools

Ok, so how did I do it?  First, I am a huge fan of Google Flights.  Of all the flight search sites out there, that one is one of the best.  The downside to it is Southwest Airlines for some reason doesn’t have their flight rates show up on Google Flights or any search for that matter.  Southwest airfare rates don’t change dramatically or very often so you won’t need to check them very much.  That being said, for these flights I used the Hopper App on my smartphone.  Where on Google Flights you can look at different dates and use plus or minus days to find the best fares on a single search, Hopper requires that you select a particular date.  This isn’t a huge deal.  I definitely recommend only searching 1 way flights.  First, it gives you more flexibility in what you do, when you book, where you fly, etc.  Second, you will almost always find cheaper round-trip flight fares if you book them as one way flights.

For this trip I set up 4-5 days one way between Orlando and Seattle / Vancouver each and the same number reversed for the flight home.  Each day Hopper notifies you of the current cheapest airfare and predicts based on historical knowledge whether you should book now or wait.  My wife and I were in the parking lot of Office Depot when the notice came through on my phone for the first flights using WestJet, I immediately booked the tickets on my phone knowing the price I saw was almost too good to be true.

Where does patience fall in this?  I had started searching for tickets 5 months prior.  It takes a tremendous amount of trust and patience to know that the right price will make its way to you if you trust the process.  As you start your search, whether you use Google Flights, Kayak, Priceline, Hopper, or some other medium, you will start to understand what the price point typically is for a flight to a given location.  For us, it was 50% cheaper to fly to Vancouver than to Seattle.  Even though we are spending 2 weeks in Washington state, Vancouver is not that far away and we all have passports and the price made sense.  It’s not always like that.  We’ve made mistakes booking flights and could have gotten them cheaper…almost always if we had waited.  Sometimes we wait too long, but for the most part we have gotten really great fares, times, stops, seats, etc for each of our flights.

Still confused or have questions or need clarification?  Send us an email or comment on the post below.

Hawaii 2007

When we started this blog, my wife and I had discussed we would only include those trips we had taken with our kids.  The more we thought about it, we had a lot to tell about all other other trips as well.  So let’s kick this thing off with our first trip as a married couple!  As the post title suggest, yes we went to Hawaii!!

This was our very first real trip together, atlas one that required quite a bit of planning.  I’ll be honest, we did not do a great job with planning, but we learned a lot.  For the first week we were there, we stayed at the Park Shore Waikiki.  Make no mistake, the website and the pictures make this hotel out to be FAR more than it is.  Yes, I realize this was 10 years ago.  However, based on my research, this hotel has not undergone significant renovations since.  The best part about the hotel was it’s location.  Our room overlooked the alley and trash dumpsters below, and the room was the smallest hotel room I had ever been in.  That being said, we didn’t go to Hawaii to spend money on the fanciest hotel.

To spend an entire week on Oahu was definitely a mistake on our part.  However, we got a great deal on the hotel room, and I haven’t mentioned this yet, but we also had planned a cruise for a week around all the Hawaiian Islands leaving out of Honolulu.  My Aunt and Uncle essentially planned the cruise portion of the trip as they were renewing their vows on Maui, so we tagged along.  Since this was so long ago, I am going to quickly recap in bullet point format the things we did on Oahu.

Oahu Activities!

  • “Hiked” / Walked up so many stairs to the top of Diamond Head at sunrise.  Truly spectacular and worth the time
  • Snorkling at Kailua.  It was a little rough the day we went, but we were able to rent gear for $20 each and had a nice time.  We got the bus schedule mixed up on the way back (before UBER) and ended up being on the Bus for probably 2 hours.
  • Dole Plantation.  Just a neat place to see all the Pineapple and learn the history
  • North Shore, a nice drive there from Waikiki if you rent a car.  Extremely calm in the summer, the big waves are in the winter.
  • Polynesian Cultural Center – The best part was the evening cultural dance, being able to see the various performances from the cultures was really neat.
  • The Beach….was very crowded, but pretty neat in that there were so many boogie boarders right at this walled pier area all going at the same time.  In addition one night there was a live band that we could hear and see from the Hotel Pool balcony.
  • Last, and certainly not least, Pearl Harbor.  Just visiting a place like Pearl Harbor can send chills down your spine. The fact that there is still oil bubbles coming from the bottom of the water where the ships are sunk is kind of surreal.

Royal Caribbean Cruise

Now onto the cruise.  First, I will never travel on a cruise by Norwegian Cruise Lines again.  It was the worst experience ever, especially for a first time cruise. They advertise Freestyle Cruising…it is anything but Freestyle.  My vision of freestyle and a Hawaiian cruise is board shorts, a t-shirt, and flip-flops 24/7.  That is not the case, especially if you want to eat dinner somewhere on the ship other than the buffet line.  I actually had to spend time at our first stop of Hilo to go to Walmart and buy pants.  We only spent 1 day at each stop which made it difficult to do anything.  However, we did spend 2 days on Maui.  The first day was spent with my Aunt and Uncle for their vow renewal, a truly beautiful ceremony with just family on an off the beat path on the beach followed by dinner at Roys.  The 2nd day we did an excursion bike ride down Mt. Haleakala .  It was by far the highlight of our trip.  At the top the temperature is in the 40’s in the summer and you are above the clouds.  As you transcend down the mountain, you only have to pedal one time for about 400 yards, you literally coast the entire way down.  Not only is it a thrill, but as you go down the mountain it is as though you are experiencing all four seasons.  Pictures and words do not do it justice, you have to experience it for yourself.  On this trip to Hawaii we didn’t truly experience Kauai like we should have, we did a kayak excursion which was great, but not what we expected.  We would have to save Kauai until summer of 2012.

 Boogie Boarders Just me trying to win a golf ball chip in contest (I got 2nd) on the cruise.

 Maui Maui Uncle & PastorThe Ceremony & Family (Me, Uncle, Aunt, Cousin, Island Pastor)


 Kauai Top of Mt Haleakala Just a Sea Turtle – Kona Kauai Na’Pali CoastKauai Na’Pali Coast Concert from hotel Pool Deck Pearl Harbor Pearl Harbor Park Shore Waikiki Waikiki Beach Kailua Kailua Dole Plantation Dole Pantation North Shore Polynesian Cultural CenterDiamond Head