Carolina Cupboard

Y’all!! Our boys have been on more flights before age 3 than I have my entire teenage years. If you’ve ever boarded a plane with toddlers, you know it’s equal parts survival mode and a comedy show.

Here’s the progression for us:

• Two under one → an actual nightmare
• Two under two → slightly less terrifying but still a nightmare
• Two and three → we’ve finally got this down (most days)

We’ve had some moments that still make me laugh/cry when I tell them, so grab your coffee and let the story time begin… then I’ll give you every single tip and hack that finally made flying feel doable.

The Time a Stranger Saved Our Lives

We rolled up to the airport late (classic), and the parking garage we always use was closed. My husband was off hunting for a spot in the next zip code, so I decided I’d just handle TSA alone with a 1 and 2 year old. We had brilliantly decided to bring two single strollers instead of one double. Picture me herding these two strollers through the TSA rope maze. It was nearly impossible.

Thankfully, a sweet man saw me struggling and started pushing a stroller for me. Then we get to the agent who “cheerfully” says, “Ma’am, you have to hold both children while collapsing both strollers and unloading all the bags.” Cool & Impossible. The same man swooped in again!! He held my baby, folded strollers, and somehow got us through security.

Afterwards, we realize that my plane was boarding RIGHT NOW. Without missing a beat, he grabs one stroller, tosses my purse in it, scoops up my 1 year old, and just… starts sprinting. I’m in complete shock. Finally after reality set in that either he is trying to help me or I’m getting robbed. SO I start running behind him pushing the toddler like we’re in the dang Olympics. We finally get to the gate, he can’t go farther, so he hands my baby to a random guy in line and yells, “Get this lady on the plane!”

I begged the gate agents to please let my husband board too or I was going to straight die on the spot. Thankfully they did. My husband came sprinting in two minutes later. I still don’t know that man’s name, but he’s family in my heart.

The Eight Water Bottles Incident

TSA allows water for formula, so my husband (without mentioning it) packed EIGHT bottles in the diaper bag “just in case.” Of course our bag gets flagged. The agent asks why we need that much water for a two hour flight to South Carolina. I smile and say, “Formula!” He gives me the longest “uhhh… okay” in history and waves me through. I pick up the bag up and it’s gotta weigh 40 pounds. I peek inside and almost died laughing. That poor agent 100% thought I was bananas. 

Okay, the tips!! Here’s what actually works now

Before you even leave the house

• One giant checked suitcase for me + both boys. My husband gets a tiny carry on size bag that we check. That’s it.
• Car seat travel bags = free extra luggage. We stuff diapers, wipes, winter coats whatever is bulky in these. 
• Packing cubes. Trust me, they shrink clothes and make unpacking feel like a miracle.
• Always pack a blanket. Planes are basically Antarctica sometimes and whatever happened to those free blankets? I have no idea but no one offers them anymore. 

Security hacks (especially military families!)

Some credit cards (Amex Platinum & Chase Sapphire) reimburse Global Entry AND Clear for free for the military…..do it. I actually like Clear better because they walk you to the front of the PreCheck line and everyone is weirdly nice compared to the rough TSA agents. Is it just me but in order to be hired by the TSA or the DMV you have to hate life? I don’t think I’ve found a sweet one to this day yet. My friends joke that I need to get a job with one of them so I can shed some sunshine in a very dark area. I like the idea of a challenge but I’m not sure I’m up for that one yet. Fun fact my boss actually told me once that I was too positive. LOL At the time I was really offended but now it’s pretty comical.

Snacks & entertainment (the real MVPs)

• Bring one gallon Ziplock of snacks (refill for the way home)
• One gallon Ziplock of brand new Dollar Tree toys revealed slowly! (Under 1 winners: soft books, spinners, teething toys, yogurt bites)

2-3 winners: reusable sticker books, mini Play-Doh, silly putty, mini Transformers, reusable pirate stickers

Pro move: Wear AirPods so your husband and you can actually talk to each other in the chaos without yelling over all the noise!

Ears on takeoff & landing

Bottle, paci, nursing, whatever keeps them swallowing. I’ll try anything that has even a 1% chance of working. DO IT!

The Water Bottle: Take Caution!!

Those leak proof kids bottles explode from cabin pressure. I once opened one and it fountained all over the people in front of us. Mortifying.

Military perks — use them!

Most airlines give active duty at least 5 free checked bags domestic (more on orders). Have IDs ready. Big airports barely look, small ones read your orders like it’s the Bible.

Airport Parking Survival

Parking is always a stressor. If we did not have the boys, we’d uber ever time however with all the car seats it’s easier for us to park and go. We found this works better for our family: My husband drops me + kids + mountains of luggage at the curb, grabs a skycap to help check bags, tips him well and instructs them to never let me stress or worry about anything, then goes and parks. Make sure you take photos and videos of your parking spot. THIS IS VERY IMPORTANT. We have lost our car multiple times. Reverse on arrival. (Charleston airport valet is heaven. O’Hare is… not.)

Arriving at the destination without losing our minds

We travel with ratchet straps (yes, really). My husband straps everything to one of those small airport carts, slings one car seat on his back, one on his chest, and pushes the Leaning Tower of Luggage while I push the double stroller. We are a traveling circus and I’m here for it.

Airport Lounges = Five Minutes of Vacation

Priority Pass (free with certain cards) or try flashing your military ID,  most lounges will let you in. Free food that’s actually good, including a kids section, clean upscale bathrooms, and complimentary everything, YES PLEASE. We will even reroute flights for a good lounge and zero shame.

And The Biggest Shout Out Of All

I truly don’t know how single parents do this. My husband is the ultimate teammate. He plans everything, carries half the airport on his body, and still makes me laugh. Ladies still dating: find you a man who travels well with kids. It’s a non-negotiable.

We’ve come a long way from those two-under-one days. Flying with littles will probably never be “easy,” but it’s now our controlled(ish) chaos and honestly? I kind of love it.

If you’re staring down a flight with your babies, take a deep breath. You’ve got this. And if all else fails, pray for a kind stranger willing to sprint through the terminal holding your kid.

Safe travels, mamas! ✈️

What’s your funniest (or most chaotic) flying-with-kids story? Tell me in the comments so I know I’m not alone!!!

Product Recommendations:

AirPlane Toys for littles: (First Shop at your local Dollar Tree they have the greatest small toy collection)

If yall can swing it and you only have one baby we are obsessed with the NUNA TRVL stroller. One button it folds up super small and it is incredible! You can even throw the car seat on top of it and it’s just amazing! You won’t regret the splurge!! Make sure to grab the additional cupholder attachment and the itz ritz stroller bag that will make for additional storage!

If you have 2, we always grab the Jeep Destination Double stroller side by side. This stroller will fit through a single door and mange the kids well. We tried the nuna double stroller and it was fine with the boys were little but as they grew no one wanted to ride on the bottom, it was just awkward.

Buy these here: https://amzn.to/4aobbxk

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Check out all my favorite travel essentials here: https://www.amazon.com/hz/wishlist/ls/3GYKDGP6PA3TX?ref_=wl_share

Check out my last post here: https://carolinacupboard.com/2025/11/25/how-i-finally-conquered-the-costco-gingerbread-house-and-saved-my-christmas-dream/