Before I share more, let me set the context for my personal toddler travel situation. Firstly, Kaiden was almost 18 months the first time we flew solo and almost 22 months the second time around. My BIL dropped us off at the airport the first time, which helped immensely. I took a Lyft on my own the second time. A bit of a different experience, but we survived!
I should also share that a lot of how your experience goes depends on your kid. Kaiden is a pretty good traveler. He doesn’t fuss much while we go through the check-in/security/waiting to board processes. He also sleeps pretty easily on planes. The noises lull him to sleep. Ha!
Ok, with all of that being said, I definitely planned and planned and planned for this most recent trip. We were traveling from Chicago to Philadelphia/New Jersey for a family wedding (a 2 hour flight). In retrospect, I thought waaaaay too much about this, but hey, that’s how I prep myself for anything that seems daunting.

I am by no means an expert at traveling with a toddler, but I do have a few tips that could possibly help another parent, so here we go…
- Plan out the logistics of your trip well in advance. I thought about everything from how I would get all of our stuff from our apartment to the Lyft to how I would carry everything, including Kaiden, into the airport. You may think I’m crazy, but I also thought about available restaurants in case of a delay. For example, where would I go to get some milk. In my defense, MDW is a fairly small airport!
- Choose a family friendly airline (when possible). Personally, I love Southwest because they offer family boarding, and the people are generally nicer and more helpful.
- Scale back and bring only what you need with you onto the plane. I brought one backpack/diaper bag, and it was filled with 2 toys, 2 books, diaper/wipes, a few snacks, an extra outfit for K, and my wallet. I find that the more we bring for Kaiden, the more he acts up. Out of sight, out of mind works best for him and us!
- Ask for help! I talked to my doorman a few days before our flight and asked if he could come up to help me bring down the suitcase and stroller. I had no shame asking our Lyft driver for extra help. And even though I didn’t need extra help when boarding this time around, I’ve asked strangers in line to help me in the past. No shame in this game!
- My final tip is easier said than done, but be confident! You know what you’re doing. It’s scary but not rocket science! And know that there are some scenarios you can’t plan for, so leave those be. Do what you can with what you have! You will eventually reach your destination, so have fun if you can.
I also think the kind of gear you travel with makes it easier (or harder) to navigate the airport. We love this stroller and stroller bag and this car seat and car seat travel bag. These things make everything 100x easier in my opinion. I like that I can carry either item on my back.
So there you have it! Like I said, I’m no expert, but these tips definitely help me prepare for solo travel with K!
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Thank you for sharing.
Travelling with a toddler definitely needs a good planning. It can be frustrating as a parent sometimes.
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