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

After collecting so many helpful tips about flying with a toddler, here’s a clear recap of what actually worked for us — and what we’ll avoid next time. We spent a lot of time in the air on this trip: six flights total, with two legs on the way to Portland (via Chicago), one direct from Portland to Maui, and three legs on the return to Richmond (layovers in Seattle and Chicago). The West Coast–Hawaii flights were the longest at about six hours each. Since Clara is under two, we opted not to buy a seat for her; she was most comfortable in our laps and — honestly — we figured a lap would be better if she got upset.

Some legs were surprisingly smooth (we were lucky to have an empty seat next to us on the flight to Maui), while others were rough — especially the overnight red-eye on the return. One of our carry-ons was Clara’s monkey backpack, stocked with small activities to keep her engaged. Below are the strategies that helped most and the ones that didn’t.

What Worked Well

• Crayons and coloring books. Coloring, pointing out colors, and simply taking crayons in and out of a box kept Clara busy for long stretches. Simple, low-mess activities like these are airplane-friendly and surprisingly absorbing for toddlers.

• Snacks and snacks containers. Goldfish crackers and Teddy Grahams were reliable calming tools. Toddlers get cranky when they’re hungry, so having a variety of familiar snacks and a spill-proof cup helped. Clara also loved crushed ice from the flight attendants and enjoyed transferring snacks between cups like a little experimenter.

• Lollipops for takeoff and landing. A reader tip suggested lollipops to encourage swallowing during ascent and descent to relieve ear pressure. They worked wonders — no ear tugs or complaints during takeoff or landing — and the sucking motion even helped Clara relax and nod off at times. Fair warning: she became very fond of them.

• Talking about the plane and people-watching. Clara loved exploring the cabin, greeting travelers, and peeking out the window. Letting her interact safely with the cabin environment and the friendly people around us helped keep her amused and cheerful.

• Airport walking and moving walkways. During long layovers we let Clara walk and explore to burn off energy. She called the moving walkways “escalators” and loved them. Airports can be surprisingly entertaining for kids — we noticed dinosaur bones at O’Hare, sculptures at Sea-Tac, and a toy store at PDX that bought us extra time.

• Committing to local time quickly. We deliberately adjusted Clara to local time right away at each stop. When we arrived in Portland at bedtime (EST), we limited her rest to a short nap, then kept her awake until a normal local bedtime. Doing the same in Hawaii — staying up until an appropriate HST bedtime and then following local nap schedules — helped stabilize her routine quickly and reduced early-morning wake-ups.

What Didn’t Work

And now the hard lessons.

• Videos on the plane. Clara loves videos at home, but inflight they were less appealing without Wi-Fi and familiar playlists. The usual KidsTV123 she watches on YouTube wasn’t available, so screens only helped a little.
• Hopes for sleep in transit. We hoped for long laps naps during long flights, but Clara usually sleeps well only in her crib at night. She napped very little in car seats or strollers, so our expectations for extended airplane sleep were unrealistic. On the trip to Portland she managed a total of thirty seconds of sleep the moment we landed. On the flight to Maui we got about an hour — better than nothing, but still short of our dreams.
• The red-eye flight. Booking an overnight flight on the way home was a mistake. We assumed Clara, typically a good night sleeper, might sleep through. Instead she couldn’t get comfortable on a full flight and woke up in a distressed state after about 45 minutes. The crew were incredibly helpful and let us spend time in the galley area to soothe her, but the red-eye disrupted the whole family’s rest and made the following day rougher than expected.

The red-eye’s lack of sleep threw off our schedule. Tiredness reduced the effectiveness of our usual distractions, and delays in Chicago compounded the exhaustion. By the time we landed in Richmond about 19 hours after leaving Hawaii, Clara had slept roughly three hours total and we were all desperate for bed.

After returning home we slept deeply for the first time and gradually re-established Clara’s normal nap and bedtime routine. She did sleep a little longer in the mornings for a few days, but her 1pm nap and night bedtime returned to normal quickly.

Lesson learned: avoid red-eye flights with toddlers if at all possible. Several flight attendants told us they rarely see kids sleep well on overnight flights, and now we know why. The stress of trying to keep a child quiet while the cabin sleeps — when you’re exhausted too — is not worth it.

Have your own stories or tips about air travel with toddlers? We’d love to hear what worked for you, or what you’d do differently next time. Sharing real experiences helps other parents prepare for flights and choose the best strategies for happy, calm travel with little ones.