Make traveling with kids a memory, not a misery
As summer approaches, I find myself thinking back to the vacations I took with my mom and dad when I was a kid.
Do you remember the chaos that accompanied your parents as they planned a vacation? Not me.
However, family travel has changed since I was a child.
Unfortunately, there were no tablets or smartphones to entertain me when I was a kid, so I was offered books. I didn’t even have a portable Mattel electronic football game.
Now, as an adult, parent and business traveler, I see the struggles of parents when traveling with their children. On my travels, I’ve sat next to the crying baby (thanks to the inventors of noise canceling headphones) or in front of the kid who has a penchant for kicking seats.
And while both of these scenarios are frustrating, I strongly suggest that you handle these situations as I did – by remaining calm and showing grace to the family. Don’t be the next ugly YouTube star yelling at flight attendants, parents, or babies.
For this piece, I’m going to regale you with two personal stories demonstrating what to do and what not to do when traveling with children. Fasten your seat belt and make sure your tray is locked, it could be a bumpy ride.
After my divorce in the summer of 2010, my son Connor and I took our first plane trip to my hometown of Chicago. Although Connor and his mother have flown before, I hoped this trip would be particularly memorable for us.
I was more anxious than ever the morning of our flight because I wanted our first trip together to be perfect. However, my stress wasn’t traveling, as I’m used to the rigors of this world, but making sure Connor had fun.
I noticed the captain of the plane hovering around while we sat at the gate waiting for the call to board. I went to see the captain and explained that it was my first flight with my son and asked if Connor could visit the cockpit. The captain gave me a big smile and granted my request.
The first lesson I would like to share from the above experience is to be bold and ask.
Despite the small glasses of drinks handed out by flight attendants, you can ask for a whole can of soda on a plane.
If you notice your child wants another snack, ask them.
Some airlines may still distribute wing pins to children, so ask.

One specific image from that trip that’s still vivid in my mind is of Connor, wearing the pilot’s hat, and me sitting in the cockpit. I have this memory of both of us because I asked for it.
When we made this trip to Chicago, the weather was hot and humid, typical of the Midwest.
Despite Chicago’s heavy weather, I hadn’t yet considered having a backpack for water, sunscreen, or snacks. As a parent, you have to anticipate all situations when you go on an adventure with children. While I felt like I had failed as a parent, this lesson did not escape me because when we visited Chicago the following summer, I was better prepared.
Growing up in Chicago and the suburbs, some places are just plain unmissable. Food is synonymous with Chicago and experiencing places I grew up in was something I wanted to share with Connor.
This brings me to my second tip: let your children share your past by creating their own memories. Plus, going on vacation with your kids shouldn’t be a diary issue — be sure to plan some downtime.
On our first full day in Chicago, Connor had no complaints as my dad and I dragged him all over downtown.
In hindsight, we should have broken things off, but this was my first trip and I was super zealous. I hoped that the new places we explored would one day be places that Connor wanted to revisit on his own.

When you are planning an event and unexpected things come up, remember that it can create great memories. This happened on our trip when I bought baseball tickets to Connor’s first Cubs game.
To our surprise the club was having a promotion that day where every kid got a free Chicago Cubs teddy bear and the Blue Man Group got to throw the first pitch which was super cool for me since I’m a big fan . .
These two unexpected perks made the day more memorable.
Another thing to remember is to take your time with your children and be present in the moment. Put the cell phone down, put the tablet in your bag and keep away from other electronic devices and enjoy the time with your kids. There is no replay button for memories with your family.
The online magazine “Parents” offers these tips and tricks for traveling with children:
- Book an early morning departure
- Talk to your children before the trip about what they can expect
- Dress in layers and avoid lace-up shoes, especially for toddlers
- Bring surprises to hand out during the flight
- Bring a smaller stroller if you can
- Seat the kids away from the aisle
- Prepare young travelers for changes in atmospheric pressure
- Plan your packing list well in advance
Now let’s discuss some things not to do when traveling with your children.
In 2013, I remarried and my wife, Ann, and I took a trip with our three children to the East to celebrate her parents’ 50th wedding anniversary.
Without direct flights, we had to fly from Denver to Las Vegas and then to our final destination, Albany, New York. By the time we were on the flight to Albany, the trip had already been long. Even today, we laugh at the idiocy of the airlines.
Lesson number three is to have patience – and oh my God, did I run out of it on this trip.

We were using a particular airline that had no seat assignment. So my bonus girl Becca sat in the window seat, Connor in the middle and me in the aisle. It was at this point in history that I lost control of myself.
We’ve dubbed Becca and Connor the “Wonderful Twins.” They could be blood brother and sister, aside from having different colored eyes. They are close in age which is attributed to my thought process regarding the seating arrangement.
During the trip, Ann and her eldest daughter, Betsy, sat together while I hung out with the “twins”. I even brought my laptop to watch movies, so having Becca and Connor sitting next to each other made sense. Unfortunately, I was wrong.
Not only did Connor not want the middle seat, but he had a meltdown. Connor’s meltdown became a chain reaction as I lost my temper.
I still think about how I could have handled the situation better taking the middle seat once I recognized Connor’s discomfort.
Oh, and neither Becca nor Connor wanted to watch movies.
As a parent, in addition to having to travel frequently for my job, I can empathize and sympathize with other parents when their children aren’t having a good day.
When Connor had his episode, there was no looking back to try and fix the situation.
I recently asked Connor if he remembered any of our trips and he said, “I know they happened, I couldn’t tell you what we did.” Maybe it’s time for me to forgive myself.
Even if you’re sure you’ve planned the perfect trip, life will get in the way.
You can have a variety of snacks for the kids, but guess what? Kids don’t like these snacks anymore.
Your sleeping baby is wide awake and restless, but you still have hours to do during the flight.
No one wants to sit in the middle seat, and everything goes wild when someone gets into that seat.
As Connor got older, one trick I found was that when I would book flights for us, I would book each of us a window seat. So I would either have him sitting in front or behind me.
We do our best as parents, but unfortunately chaos will be part of the holidays and part of life.
Our parents didn’t have the luxury of technology that our children have today, they figured things out when problems arose. If a screaming child was in the back seat, a parent might intervene: “Don’t make me turn this car around.
You can’t control everyone, and that includes our children. So when traveling with children of all ages, try to have fun.
Will your toddlers or elementary school students remember everything? Preferably not.
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