When Is Flying With Toddlers Worth It?

Very few trips justify unleashing that level of crazy. Drive when possible.

Sometimes, though, flights are the only sensible option to minimize time away from work. Families are often spread out across the country or, if you’re landlocked, beach vacations necessitate a flight.

How do we know what trips justify the week of packing and Dollar Tree goodie bag prep, of folding and unfolding strollers at security and the gate while wearing a baby and trying to keep the others close?

Napa Trip

Flying Solo As a family, we’ve been blessed to travel a good amount. Before kids, it was easy and carefree. When we got bumped while visiting family and found a Travel Zoo deal, we took a quick trip to Napa. We flew down to my cousin’s wedding in Virginia and traveled to Kentucky to visit friends and do a brewery tour. We lived that first year of marriage to the fullest.

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Flying With One After our first, travel got a bit more complicated. We flew or drove between Nebraska and Tennessee regularly for my husband’s work and to see both of our parents before my oldest started school.

This infant phase was easy but we had no idea. I would feed Ella as we took off and then she would nap in my lap for the good majority of the flight. Looking out the window and being held by her daddy mesmerized her.

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A True Gift at Chicago O’Hare

Layovers were a bit of a pill once she started walking, but we found the kid areas and flocked to them immediately (see above).

Flying With Two After two kids, travel got a bit saucier. Part of that was because our oldest two are 18 months apart and thus travel used to involve two sets of diapers and simultaneous terrible two and three tantrums.

It also felt like our lives had to revolve around their nap schedules for the sake of everyone involved and when the flights didn’t coincide we were those people everyone was side eyeing on the plane. We let them have their own rolling suitcase on this trip and immediately regretted it. Now we stick to a backpack for each kid.

Flying With Three Now with three kids, we are officially outnumbered and, while this ain’t our first rodeo, the luggage and layover logistics make us always feel like we’re running for the gate.

Hair has been ripped out, we have all been force fed plane snacks against our will (reenactment below), my face has been clawed, poopy accidents have happened on my lap when you have to stay buckled without a backup outfit packed, and many planes have endured all the ear pressure screams.

When you land and pulling up to the gate is delayed while your kids are losing it, hoo boy you’re just done. You’re convinced that you’ll never do it again. You’re asking, “Why did I do this to myself?” and sure that no trip is worth this type of crazy.

The Rare Exception to the Rule

All five of us flew out to see both of my grandparents this weekend over Easter. They are all in their 80s and, outside of a few health issues, are holding up pretty darn well. I try to make it out once a year to see them and family in the area. My parents and brother also traveled up from Tennessee to join us.

This trip, because of the Southwest companion pass, taking advantage of the last weeks of a free lap baby, and a school break, we decided to all go out.

I live in the backpack carrier just in case

For some reason, our one year old decided to fast from naps on the flights there so the second leg was a bit of a scene trying to nap backpack bounce around the snack cart like Frogger. Look at that picture. It’s like she knows.

We arrived late and spent the first night in a hotel so that we could explore Philadelphia on Rachel’s birthday the following day.

It was an incredibly rough night fighting colds and coughs, but that next morning as I walked to Walgreens and breathed in morning commute Philly, I was beginning to recover from the toddler travel haze. As I arrived back at the hotel lobby to find my grandma, Nanny, waiting for my aunt to park the car, my excitement grew to see everyone and start our day.

We took our birthday girl to see Philadelphia including yummy Reading Terminal donuts, Independence Hall, a trip to the Temple Newman Center to see old friends, lots of cheesesteaks, and a cute downtown park.

The next morning we picked up my parents at the airport and drove to my grandparent’s house, Grammy and Gramps, who were kind enough to host all of us, my brother, and his girlfriend.

We enjoyed Philadelphia hoagies, cheesesteak, and pizza that still remain unrivaled and then checked out a local brewery.

The following day we went to Nanny’s place who had organized an Easter egg hunt in her apartment with prizes for each girl. We then went to her complex’s egg hunt because the weather was gorgeous and they needed more candy. 😉

My mom took the kids back to her parent’s house after to dye eggs while we drove to the casino where I shadowed Nanny and her winning ways.

On Easter Sunday, we awoke to Easter basket joy from the Easter bunny and Grammy and Gramps. We went to a nearby Easter service and came home to Grammy setting out a six-course Easter meal in her kitchen. This lady is recently off of a double knee replacement surgery. What a wonder woman.

A few of my aunts and uncles came over and we did an Easter egg hunt in their backyard followed by that amazing meal and a birthday party for Rachel.

I’ve never been more thankful for and impressed by them.


I know we are blessed that three of my grandparents are with us. I’ve felt the strain that living across the country in Pennsylvania, Tennessee, and Nebraska puts on getting together. I know that we’ve never all been together at once.

Watching the news and American Idol with Gramps while he did the newspaper’s Sudoku for the day reminded me of staying with them growing up. Seeing Grammy whip up a fantastic meal to host her family and organize the birthday party made me think of all of the wonderful holiday parties she used to throw. Laughing with Nanny at the casino took me back to our weekly Sunday Rummikub sessions at their house.

Getting together all four generations was worth every scream and stress on that plane ride.

Thankfully, on the flight home, they all gave in and napped. Thank you, Jesus.

Easter travel got us like ^

For me, I look at it like this. If finances or reward points allow, for a once in a lifetime family trip or an extended vacation (three-night minimum) to a kid-friendly location, i.e. everything must be walkable, a flight is worth it.

For us, two nights in a hotel, no matter the locale, aren’t worth the hassle of two days of flying. If the trip is short, make it driveable or put it on hold until they can all be mesmerized by a LeapPad for the flight.


What trips have you found were worth taking the whole family? What trips did you find out too late were just not worth it?

2 thoughts on “When Is Flying With Toddlers Worth It?

  1. Aunt Diane says:

    Your article was great, the greatest gift was letting you and your kids enjoy the family, we are so blessed that you overcome the travel obstacles to enjoy us😀❤️😀

    Like

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