First thing to keep in mind is that airlines are required to allow you to gate-check a stroller and counter-check one carseat for each child traveling with you. These do NOT count towards your paid/alloted checked or carry-on luggage. I travelled with our Minno Twin Double Umbrella Stroller that I recommend to ya'll all the time. I can easily close it with one hand when holding Clark which is super important as you are standing on the gangway trying to get it closed. It also has under-carriage storage which most umbrella strollers don't have. Highly recommend this double stroller. I always take a stroller and check it at the gate. Even when Oliver was little and I'd carry him in my Bjorn, I'd still take a stroller to hold our bags while we walked around.
I bought these carseat bags on Amazon. They are functional and cheep which was my main goal. They did get pretty beat up on the trip but nothing ripped so I'll call that a win. Definitely find something with a strap to put your carseats in so you can easily cart them from the car to the check-in station or from the baggage claim to your ground transportation.
Tip: I wrote our name and address in sharpie on the outside of the bags.
I did something different on this trip which made a HUGE difference. I had a car waiting for us at the airport that we had with us the entire trip. Usually I just have someone pick us up and we ride with them during the trip, but having our own vehicle was so much easier. We didn't have to worry about space or how to transport everyone around while on our trip. It also gave me my own space to store the stroller and luggage so it wasn't crowding up the house or people's cars the whole time.
For our trip to Alabama, we drove the 2018 Mazda CX-5 and it was FANTASTIC! SOO roomy, such a smooth drive and surprising great on gas. It got the same gas millage my tiny Toyota Corolla gets. The trunk space was so great for our luggage and stroller and we could easily fit both carseats and a 5th person in the backseat without squishing anyone (my current problem with my car!). The carseats were so easy to install because they had the clip bars in an easy place to access which is huge when trying to get kids in the car by yourself in a hurry.
Tip: I put Clark in his carseat outside of the car and let Ollie sit in the front passenger seat with a snack while I put the carseats in. I put Clark's base in first, snapped him in and game him a snack. Next I put Oliver's carseat in and moved him back to his seat. AFTER they were in I loaded the stroller and luggage. Not as hectic as I thought it would be!
There is no so thing as too much entertainment on a flight! The key is saving the best for last (aka electronics). If you start off with videos or video games then you are pretty much stuck letting them do that the whole time.
I went ham at the Target dollar spot on activities for the plane. I bought: sticker books, ABC flash cards, dinosaur felt activities, magic water pen coloring books, and books. The first thing we started with on both flights was stickers. They are time consuming and keep them in their seat. I let Oliver decorate the window and walls of the plane next to his seat with stickers (they come off super easy but double check one sticker before you let them go wild just in case!). He did this for about 30 minutes on both planes. It also takes a good 5 minutes for them to clean up at the end so don't wait till the last second to clean up.
On the way home I was so tired so we started with stickers, read books, did his felt board and then I finally gave him my phone to play his ABC games while Clark and I slept. I was able to hold out on the phone for the entire departing flight!
Tip #1: For anything messy like flash cards or felt boards, wait until the seat belt sign goes off and let them kneel on the floor and use their seat like a table.
Tip #2: Avoid anything with wheels. Cars are a nightmare because they slide down under the seat and the people behind you have to keep getting them. If your kid is obsessed with cars, distract them with car stickers, books about cars, or car felt boards instead.
I try to avoid buying food and drinks in the airports because they are so expensive. I brought all the snacks we would need and an empty water bottle we could fill up after we went through security. Don't forget to save some snacks for the car ride from the airport. I also brought these silicone lids from Boon to make a regular cup into a sippy cup that I used on the drinks we got on the plane.
Tip: Save the best snacks - AKA fruit snacks or anything chocolate - for that car ride from the airport. They are liable to be tired and cranky and not keen to get into carseats so have something tempting to distract them!
Oliver is old enough to sleep in a bed, but traveling with a baby is a bit trickery. My parents had a pack-n-play for us but I also brought Clark's Dockatot and I'm so happy that I did. I packed it in a duffle bag and filled all around it with our clothes. Having that familiar sleeping space made it so easy for him. If you have any way to bring some part of their sleep space with you I'd recommend doing so.