Flying with a Toddler: What Worked and What Didn’t

After getting so many helpful suggestions about flying with a toddler, we wanted to share a concise recap of what actually helped (lollipops!) and what didn’t (red-eye flights). We were on the move a lot: six flights in total. Two flights got us to Portland (with a layover in Chicago), one was direct from Portland to Maui, and on the return we had three legs back to Richmond with stops in Seattle and Chicago. The West Coast–Hawaii segments were the longest at six hours each. Because Clara is under two, we opted not to buy her a separate seat—she’s usually most comfortable in our laps, and buying a seat wouldn’t necessarily have prevented any fussing.

Our goal was simple: keep Clara content and as quiet as possible while encouraging sleep whenever we could. Of course we also hoped to enjoy the trip ourselves when the opportunity arose.

Some flights went surprisingly well (we even had an empty seat next to us on the way to Maui), while others bordered on nightmare—especially the red-eye home. One of our carry-ons was her monkey backpack, stocked with little activities and snacks. Here’s what reliably helped:

• Crayons and coloring books. These were a major hit. Coloring, identifying colors together, and taking crayons in and out of their box kept her occupied for long stretches.

• Snacks. Goldfish crackers and Teddy Grahams were lifesavers. Kids get cranky when they’re hungry, so having familiar snacks and a water cup mattered. She also loved crushed ice from the drink service and enjoyed moving snacks between cups like a little scientist—simple things that buy time.

• Lollipops for takeoff and landing. Someone suggested lollipops to encourage swallowing during ascent and descent to relieve ear pressure. Clara loved them and they genuinely prevented any ear-related complaints. The sucking motion even made her a bit drowsy, which was an extra benefit.

• Talking about the plane and people-watching. She enjoyed exploring the cabin, greeting fellow passengers (“Hi people!”), and peeking out the window. Engaging her by talking about the plane and the view kept her curious and happy. On one flight she got very friendly with a seatmate—thankfully he was a good sport.

• Moving walkways and airport visits. Long layovers meant we needed activities on the ground too. Walking the terminals, visiting airport displays, and riding moving walkways (she called them “escalators”) helped her expend energy and stay entertained between flights.

• Committing to local time immediately. We decided to switch Clara straight to the destination time zone upon arrival. That made transitioning between time zones easier. In Portland we kept her awake until local bedtime, and in Maui we adjusted her schedule the same way. After the first night she fell into a reliable routine with normal naps and wake times, which simplified the rest of each stay.

Now, what didn’t go well:

• Videos. Though she loves videos at home, in-flight screen time didn’t hold her attention. Without reliable airplane Wi-Fi to stream her favorites, videos were only a minor distraction.
• Sleeping in laps and seats. We’d hoped she’d nap more on flights, but Clara generally sleeps best in her crib. Car seats and stroller naps don’t translate to lap sleep for her, so long uninterrupted sleep on planes was rare. We did manage an hour on a six-hour flight and a few short dozes, but it wasn’t the restful travel we’d imagined.

The red-eye flight. Booking an overnight flight turned out to be a mistake. We thought a red-eye might work because Clara usually sleeps well at night, but she couldn’t get comfortable on the crowded overnight flight. She slept for around 45 minutes before waking in distress, and we spent much of the flight calming her in the galley where the attendants were incredibly helpful. The result: the whole family was exhausted, and the rest of the day was difficult. We learned from flight attendants that many kids—even great sleepers—rarely sleep well on red-eyes, so we’ll avoid them in the future.

By the time we finally reached Richmond we’d been traveling for about 19 hours. Clara managed perhaps three hours of sleep total during that stretch, shared between both of us. When it was over, the relief was immediate: we all slept deeply and caught up on rest the next day. After returning home we re-established Clara’s normal nap and bedtime schedule and she was back to her usual rhythm quickly.

In short: packing quiet activities, favorite snacks, lollipops for ear pressure, and committing to local time were our winning strategies. Avoiding red-eye flights with a toddler is now a hard-learned rule for us. If you have your own travel tips or stories about flying with a toddler, we’d love to hear them.