After getting a bunch of helpful tips from readers about flying with a toddler, we wanted to share a concise recap of what worked (lollipops!) and what didn’t (two words: red eye).
We spent a lot of time in the air: 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 segments were the West Coast–Hawaii flights at six hours each. Because Clara is still under two, we didn’t buy her a separate seat — she’s most comfortable in our laps and we figured that might keep her calmer. Our plan was simple: keep Clara content and as quiet as possible while encouraging sleep whenever we could, and try to enjoy the trip.
Some flights were smooth (we even had an empty seat beside us on the way to Maui) and others tested our patience (looking at you, red eye). One of our carry-ons was Clara’s monkey backpack, which we filled with small items to keep her engaged. Here’s what worked best for us:
- Crayons and coloring books. Simple and versatile — coloring, naming colors, or just taking crayons in and out of the box kept her happily occupied for long stretches.
- Snacks. Goldfish and Teddy Grahams were lifesavers. It’s easy to forget that a cranky toddler might just be hungry, so we carried multiple snack options and a cup of water. Clara also loved chewing on crushed ice from drink service and experimenting with pouring snacks into different cups.
- Lollipops. Several readers suggested lollipops to help with ear pressure during takeoff and landing. Clara was a big fan and they worked exactly as intended — no ear tugs or whining during ascent or descent. The sucking motion even helped calm her and make her a bit drowsy.
- Talking about the plane and greeting people. Clara loved exploring the cabin, waving and saying “Hi” to fellow passengers. She enjoyed standing up to look around and loved the window views. Her cheerful greetings won over many fellow travelers and made the flights more pleasant.
- Moving walkways and airport exploration. We had a few long layovers, so we let Clara walk and run around to burn energy. She was fascinated by moving walkways (she called them “escalators”), and different airports had fun distractions — a dinosaur skeleton at O’Hare, sculptures at Sea-Tac, and a toy store at PDX. Those distractions helped a lot during long waits.
- Committing to local time immediately. We decided to switch Clara to local time right away whenever we changed time zones, and it paid off. In Portland, she was exhausted on arrival so we gave her a short nap, then kept her awake until a normal local bedtime. In Maui we did the same, keeping her up until around 8pm HST the first night and then returning to a regular 1pm nap schedule. Resetting her schedule each time helped her settle into a normal wake and nap routine quickly.
Now for what didn’t go well.
- Videos. Clara loves videos at home but wasn’t very interested on the plane. With no Wi-Fi for YouTube, she was frustrated and screen time didn’t buy us much peace.
- Sleep on the plane. We’d hoped she’d nap in our laps, but she usually only sleeps well in her crib at home. On the trip to Portland she slept for exactly thirty seconds as we landed — the only nod she gave during nine hours of travel. The extra seat to Maui helped and we got a one-hour nap on that flight, but in general long stretches of sleep were rare.
- The red-eye flight. Booking an overnight flight was a mistake. We thought Clara — usually a good night sleeper — might sleep through the flight, but she couldn’t get comfortable and woke in a screaming, terrified state after about 45 minutes. The crew was incredibly kind and let us sit in the back to rock and feed her so the rest of the cabin could sleep. That helped the other passengers but left us exhausted. A short nap on the subsequent flight helped, but the red-eye threw off our whole day.
The red-eye’s aftereffects lingered: we were all tired and cranky, many tried-and-true distractions lost their appeal, and delays added to the strain. By the time we landed in Richmond about 19 hours after leaving Hawaii, Clara had slept roughly three hours total. We were relieved it was over and immediately crashed. After missing a night’s sleep, the three of us slept until 1pm the next day — fifteen glorious hours.
We’ve learned our lesson: no more red-eye flights with a toddler. Several flight attendants told us kids rarely sleep on overnight flights, even those who are usually good sleepers. If you can avoid it, do. The pressure to keep a child quiet in a dark cabin while everyone sleeps — all while you’re exhausted — is not worth the risk.
Have your own toddler travel stories or tips to share? We’d love to hear what has worked for you on flights and long travel days.