Flying with 2 Toddlers for the First Time

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We took a weekend trip with our 3 year old and 20-month-old. One of our best friends was getting married, my husband was a groomsman, and they asked Lily to be a flower girl. We took a 2.5-hour flight there, and 3.5-hour flight back. My children did so well on their first flight. We planned for a nonstop flight (which meant leaving at 5am for the return flight) but it was well worth it.

Getting through the Airport

Baby carrier – I used my Lillebaby carrier to take my 20-month-old son through the airport. This was especially helpful for the early morning – James slept during the car ride, transferred to the baby carrier and continued sleeping all the way until we sat in the plane. Some people opt for strollers and you can gate check it but we didn’t need a stroller at our destination so it didn’t make sense for us on this trip. I loved having both of my hands and only having to make sure Lily was with us, since James was on my back. He cooperated really well and was content to just watch everything from my back, which we weren’t sure about as this was his first time in the carrier since learning to walk.

We chose to check two of our suitcases because checked bags are still free with Southwest and logistically it would be difficult to go through an airport with two toddlers, backpacks, and carry-on luggage. In hindsight, I am so thankful we decided this. It was well worth the wait at the luggage carousel. If we had to pay to check our bags, we would have probably still checked one but I might have downsized and tried to squeeze it all into carry-ons, which is a lot more to maneuver through an airport and plane with.

We also tried out packing cubes because several people told me how much they loved them. I used this set from Amazon. I did find them useful for the kids’ stuff, particularly in our backpacks on the plane. I used one for the coloring supplies and cars, and I wish I had used another one for all of our snacks. I also used the larger ones to separate Lily’s clothes from James’ in their suitcase. I always use the hotel-provided laundry bags for our dirty clothes, which help separate things on the flight home as well.

Going through security was actually very nice on our way there – they told us we didn’t have to empty bags, didn’t have to take the kids’ shoes off, and James stayed in the carrier (I just needed to get my hands swabbed since I was carrying him). I know every airport is different as far as how much you have to unpack for security, but I was prepared to take out our laptop, tablet, and ziploc bags of baby food pouches.

Renting a car when we arrived took much longer than anticipated: my husband stood in line for 2 hours to get the car we had reserved online. He took our 3-year-old and the tablet while I found our checked luggage at baggage claim with our son in the carrier on my back. Once he got the car, he circled around to baggage claim to pick us up.

Entertainment for Toddlers

Gel stickers – note that with these particular gel stickers, they worked well and were super entertaining on the plane but it is easy to peel the picture off of the gel. They stick to the plane window and tray tables, so both my daughter and son could have their own playing area, but once my daughter got home she tore all the pictures off. We also got some other stickers that said they were gel but were actually 3D stickers (hard plastic with very sticky backs, not reusable gel stickers). After a few mins it started to leave residue on the tray table and window so I had to put them back away. I was disappointed and so glad I also got this vehicle set as it entertained my kids for a good chunk of time.

Tablet – we have a samsung tablet they play with sometimes at home. We have downloaded a few apps with different educational preschool games on them. For this trip, we also downloaded prime video and Disney+ and then downloaded two of their favorite movies and a few of their favorite tv show episodes. We bought these headphones and a headphone splitter for them to use on the plane, but apparently they don’t need the sound as they watched their shows without the headphones after a few minutes. We tried the headphones at home and they liked them, but decided they didn’t need sound on the plane. They didn’t seem to mind and didn’t ask for the sound so I didn’t insist on them using the headphones.

Toys and Coloring – Lily packed her favorite stuffed animals, and I brought a few of James’ favorite vehicles to play with. I also packed some portable coloring packs from the dollar spot at Target that was entertaining for a few minutes (it included a small coloring book, stickers, and crayons). At the dollar spot I also found some imagine ink coloring packs.

Packing List

  • Normal diaper bag supplies
  • Tablet/iPad for kids (with downloaded movies, favorite tv episodes, and games)
  • Tablet and phone chargers
  • Portable battery for tablet and phones
  • Kids headphones -these fold up a little (we practiced at home with Lily beforehand)
  • Headphone splitter in case they both wanted to listen (it ended up that neither of them listened long to the shows but oh well)
  • Downloaded episodes of shows/movies on tablet and phones
  • All the snacks (pancakes from the day before, baby food pouches, applesauce pouches, crackers, snack bars, string cheese, and they ended up loving the snack mix from Southwest)
  • Empty water bottles (we filled up once we got past security)
  • Applesauce pouches for takeoff/landing (people also suggest juice boxes but my kids like applesauce better)
  • Jackets
  • Copies of birth certificates (we were not asked for them but better to have them than not)
  • Gel stickers
  • Imagine Ink coloring packs (no mess markers)
  • New coloring packs (small coloring book, stickers, and crayons)
  • Lollipops for being quiet at wedding reception and for takeoff/landing
  • Neck pillows (no one used them haha)
  • Wedding day outfits including shoes
  • More diapers and wipes than I would need (though, if needed, we could always go to a store and grab more)
  • Pajamas for each night
  • Day outfits for all 4 of us
  • Hygiene products for all 4 of us (hair gel, deoderant, toothbrushes, hairbrushes, etc)
  • A crib sheet (the hotel provided us with a pack n play to use)
  • My son’s blanket from his crib to help him sleep in the pack n play (which is good, our hotel room got cold!)
  • Toys for the hotel room – including a water coloring mat
  • Daily vitamins/meds
mother with baby and toddler under an airplane with text flying with 2 toddler show we did it our first time

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