After collecting lots of helpful advice about flying with a toddler, we wanted to share a clear recap of what worked (lollipops!) and what didn’t (two words: red eye).

We flew a lot on this trip: six flights total. Two on the way to Portland (with a layover in Chicago), one direct from Portland to Maui, and three on the way back to Richmond (layovers in Seattle and Chicago). The longest legs were the six-hour flights between the West Coast and Hawaii. Since Clara is still under two, we didn’t buy her a seat—we figured she’d be most comfortable on our laps and, honestly, that buying a seat might not have prevented a loud meltdown. Our plan was simple: keep Clara content and encourage sleep where possible, try not to disturb other passengers, and enjoy the trip as best we could.

Some flights were surprisingly smooth (we even had an empty seat next to us on the way to Maui), while others came close to nightmarish—looking at you, red-eye return flight. One of our carry-ons was Clara’s monkey backpack, stocked with small items to keep her engaged. Below are the strategies and items that truly helped us get through the flights.

• Crayons and coloring books. These were probably the biggest hit. Coloring, naming colors together, and the simple delight of pulling crayons in and out of a box kept her occupied longer than we expected.

• Snacks and drinks. We packed Goldfish crackers and Teddy Grahams and kept a water cup handy. It’s easy to forget hunger is often the root of fussiness, so having familiar snacks made a big difference. Clara also loved the crushed ice flight attendants offer and enjoyed transferring snacks between cups—simple play that bought us time and calm.

• Lollipops. Several people suggested lollipops to encourage swallowing during takeoff and landing to relieve ear pressure, and they worked like a charm. Clara used quite a few of them before, during, and after flights, but we’d do it again in a heartbeat since they prevented any ear-pulling or whining during ascent and descent. The sucking motion also seemed to help her relax and sometimes doze off.

• Talking about the plane and social interaction. Clara loved looking around the cabin, waving and saying “Hi” to fellow travelers, and pointing out things she noticed. She delighted in people-watching and greeting strangers—by the end of the trip she had comfortably schmoozed a surprising number of fellow passengers. Window views were an easy win too.

• Airport movement and sights. We had some long layovers (up to three hours), so we let Clara stretch her legs. She loved moving walkways (she called them “escalators”), and exploring airport attractions kept her engaged—O’Hare’s dinosaur skeleton, Sea-Tac’s sculptures, and PDX’s toy store were memorable distraction points. Walking and letting her explore helped burn energy and kept moods better than sitting still for hours.

• Committing to local time immediately. We decided to adopt the local time zone as soon as we landed at each destination. That strategy helped reset Clara’s internal clock quickly. In Portland we let her take a short nap on arrival, then woke her for dinner and put her to bed at a normal local time. In Maui we kept her awake until a regular local bedtime the first night and then resumed normal naps and evenings. This made wake times and naps predictable for the rest of each stay and reduced early-morning wakings.

Now for what didn’t go as planned.

• Videos. At home Clara loves videos, but on the plane she showed little interest. Without reliable Wi-Fi and her favorite content available, screen time helped only a little and sometimes led to frustration.
• Expectations about sleep on planes. We’d hoped for long stretches of sleep with Clara curled on our laps, but she tends to sleep best in her crib—not in car seats or strollers. On the way to Portland she slept for exactly thirty seconds as the plane landed. That was it for that nine-hour travel day. We did manage about an hour on the six-hour flight to Maui when we had an empty seat, which felt like a small victory.

• The red-eye home. Booking an overnight flight was probably our worst move. Although Clara is generally an excellent night sleeper, the crowded plane and inability to get comfortable prevented a good night’s rest. She managed roughly forty-five minutes of sleep before waking inconsolably. The crew were incredibly helpful and let us spend time in the galley area where Clara could snack and be rocked quietly, which kept the rest of the cabin undisturbed. Still, the night was sleepless for us. We were grateful for a short nap on the subsequent flight, but the red-eye left us exhausted and grumpy for the following day.

The red-eye disrupted the rest of our return day. Things that had previously entertained Clara no longer held her attention, and flight delays compounded everyone’s fatigue. We finally landed in Richmond late in the evening, having been traveling for about 19 hours. Clara probably slept around three hours total during that stretch; we took turns catching bits of sleep until we all finally crashed and slept deeply the next day. After a long recovery nap day, Clara returned to her normal nap and bedtime schedule with only a slight shift in morning wake time.

The biggest takeaway: avoid red-eye flights with toddlers if at all possible. We heard the same advice from flight attendants—many say children rarely sleep on overnight flights. Traveling with a tired child while trying to keep the cabin quiet is a real challenge and not one we’ll repeat soon. If you have other tips or stories about traveling with little ones, we’d love to hear them. Or if you’ve survived a red-eye with a toddler, please share your wisdom—we’ll be smarter next time (we hope!).