Survival Guide: Flying alone with a toddler and a baby


We’ve traveled quite a bit with our kids. It’s always been all together though. I have flown with Rowan by myself twice but never both of them. The thought of being out numbered by kids on an airplane has had me totally freaked me out. When the chance to go to Florida came up though, I bit the bullet and decided to conquer my fears. All in all it wasn’t too bad. Finley was pretty fussy to be honest but I just found out she has a double ear infection so I think that had something to do with it. The lovely folks over at Lily Jade just send us this gorgeous designer diaper bag and it totally saved my life on this flight. When traveling by yourself the less you have to carry the better. It will make it so much easier and make you less stressed if you don’t have tons of bags to drag along. Because lets face it, you are already going to have your hands full with the kids. The fact that this bag can be worn as a backpack was seriously the biggest help on this trip. Plus, the inside is HUGE. I was able to pack everything I needed for our day of travel for both kids in there.


Here are some other tips I found really helpful when traveling by yourself with your kids…

1. Bring a stroller. The stroller was essential for getting everyone around the airport. Especially between connecting flights. We seriously had a Home Alone moment (running top speed to make connecting flight) and if I didn’t have the stroller we never would have made it. We have a double Maclearn. We LOVE it!!

2. When we first got to the airport and checked in at the desk, we asked if Kev could get a special clearance ticket to go through security to help me with the kids. Did you know you can do that? I never knew that until a few years ago. Not having to go through security by yourself is so helpful. Besides, then he gets to stay with us until the moment we get on the plane.

3. Plan your flight (if you can) for when your kids will be well rested. I use to think it would be helpful if it was around nap time because then maybe they would fall asleep on the plane. HA! Chances are (well, with my luck), they won’t and then you are left with an over tired, extremely fussy baby. It’s better to have a happy, rested little one to play with.

4. Just give yourself a break. It will be tough and it will be stressful. Just know you are doing the best you can. The calmer you can stay the better everything will go. Forget if you can, that you are on a plane with other people. I know it’s so hard! As soon as Finley would start crying I could feel my blood pressure rising. Just remember not everyone is annoyed they are crying. I know when I hear a baby crying I just feel sympathy for the parents and well, most of the time I don’t even notice.

5. Snacks, toys and activities. Here is everything that I fit into my Lily Jade bag for the trip. 1. Mini Eggs (these were for me!) 2. Coloring and activity books for Rowan 3. Headphones and iPad for Rowan loaded with new games and movies 4. Her little toys she picked out for the trip (cheetah, my littlest pet shop pony and Cinderella) 5. A few toys for Finley. She doesn’t “play” with much, just gets into everything that isn’t a toy 6. Her bottle 7. Snacks 8. Teddy 9. My iPhone and charger 10. Aden and Anais swaddle blanket 11. Diapers, wipes and kleenex 12. Hand sanitizer 13. YumEarth Organics Vitamin C gummy bears and lollipops









*A Lily Jade bag is definitely an investment piece but their quality and function will last you well beyond the baby years. I have the Caroline bag and it’s on sale at the moment! A must have for your baby registry.

Dress: Old Navy
Sandals: Sam & Libby from Target
Scarf: Target
Watch: Michael Kors
Madeline Bag: c/o Lily Jade

On Rowan:
Dress: gift from Little Hip Squeaks
Floral Crown: gift from The Wishing Elephant

On Finley:
Shirt: Gap
Shorts: Gap
Scarf: gift from Little Hip Squeaks

  1. Thanks for the post! Your girls are adorable!

    I had a I can do anything supermom feeling when I booked a return flight for myself and my two girls (2.5 years and 2.5 months). Before the flight, I freaked changed things around and had my husband fly back with us. I’m sure it’s possible but I wasn’t ready to try it!

  2. love this blog, it’s so unique. definitely recommending it to my aunt x

  3. Alison Geis •

    That bag looks awesome! I bet it’s so nice to just sling it on your back and be hands free.
    Could you also do a post (maybe when you get home) on how you pack for your kids? Do they have their own suitcase or does it all go in yours? Have a great time with family! <3

  4. I just flew home from Vancouver to Toronto with a 3 year old and a 6 month old! I was pretty confident all would be fine but boy was I wrong! My first mistake was being away for 3 weeks, by the time we left both kids were way over tired from missing multiple naps, being on no schedule, over stimulation, endless treats from family and just being “done” from being away from home. The second mistake was booking a return flight in the evening also thinking they would sleep, by the end of the flight my son was BEGGING me to lie down and my daughter was so over tired she was beyond falling asleep and when I was finally able to get them to sleep we hit turbulence and the seat belt sign came on an off 5 times! So that meant I had to wake them both 5 times to get seat belts on!! Many other things went awry, MANY, and I had a good cry when Daddy picked us up but I will do it again, but will plan a bit better:) I also bought a great Diaper bag by BOKEN that was super light and could be used as a back pack! And by the way, your kids are super adorable!

  5. I’m so not a diaper bag person but this one is gorgeous… already placed an order for one of my own. With baby #2 on the way I might actually use one this time.

  6. you’re wearing a scarf……. in florida…. DRIVE MORE SOUTH.

  7. I didn’t even realize that was the diaper bag until the solo picture! Looks killer with the scarf.

  8. oh i had no idea about the clearance ticket, what a find! the security checkpoint is by far the worst –removing shoes, liquids and chasing even one baby on your own, nightmarish! thank you for the tip. also the bag is really darling and seems super functional.

  9. The real question is, how did you get those photos if it was just the three of you? 😉
    Cute post, and so insightful! Thank you 🙂
    xo, laura

  10. Good work, mama! Love this list–and if you want an addition to it, be ok with asking strangers for help (like when you need to fold up the stroller or put stuff in the overhead bin). I just handed my baby to the lady in line behind me, and what was she going to do? Say no I won’t hold your cutie kid while you fold up your giant Bob-contraption of a stroller? 😉 Hee hee! P.s. Love your blog.

  11. Wonderful tips and great job! We have flown a number of times with Penny (I have never done it alone- kudos to you!) but the test will be in May when we travel 11+ hours to Europe. Can you let me know what type of headphones you have for Rowan? Penny will be 22 months and I think old enough to keep them on but i’d like to get them and let her get used to them first. Thanks so much!

  12. Thank you so much for this travel info, I am off in a week with my two toddlers on a plane by myself for the first time! A little apprehensive!! Could I also ask what size you where in the Old Navy dress. I am looking at getting it, but the sizing is different to Australian sizes. Thank you so much for such a great blog 🙂

  13. LOVING that bag! I’ll have to go check it out. Also, I love those lollipops! I was so happy when I found them because they really keep my daughter calm in public after she’s out for long periods of time and bored haha. They just seem so much better since they have vitamins and are organic! Also, I’ve saved these tips for when I fly with my daughter this year. She might not be two kids but these tips will help calm my extremely anxious nerves!

  14. I give you so much credit! I would be so worried flying with two kids. Getting the clearance ticket seems like a great idea :]

  15. love your outfit and the bag!!

    xo josephine

  16. I’ve never flown solo with kids, but I’ve taken tons of long car trips with little ones. And I have to tell you, it gets SO much easier. Mine are 5 and 2, and I no longer dread those long trips. (I think part of it is that any trip seems great compared to the ones where they were both under 3 and would both cry for HOURS!)

    Also…. love your outfit! You look so great. I think a trip to Old Navy to check out that dress might have to be planned for this weekend!

  17. Crystal •

    Hello Jen,
    I wanted to ask about your stroller, did you use it from birth with Finley? I have a one year old and I am due with my second right away (as in it could come any day), so we are trying to get a light weight double. I just worry about a new born in that big chair… I tried it in the store and really liked it, as did our one year old. Let me know your thoughts! Thanks! Love your blog.

  18. Elissa •

    What are Rowan’s headphones? Plan to be traveling with my toddler and infant soon…

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Hi, I'm Jen!

Welcome to my personal lifestyle blog. It features topics such as motherhood, family life, fashion, cooking, and all sorts of adventures. I hope you enjoy what you find!

Jen Loves Kev