Here are the tips that I found most helpful:

Bring your car seat and stroller and check both right at the gate. Most airlines allow you to bring 2 items for free including: travel crib, stroller and/or car seat. I made arrangements with the friend we were staying with to have a travel crib set up for us when we arrived at her house. You will definitely need a travel crib, so I would suggest to have all 3 on your trip. I brought his carrier too, but didn't find it as useful at the airport as other blogs mentioned. I used it on hikes on our trip, so I would still recommend bringing it as it will come in handy at some point on your trip if you plan on going on lots of adventures! Dax sat in the car seat attached to the stroller while we were in the airport. I stored my carry-on (diaper bag) in the stroller when we were walking around the airport, so found the stroller really handy. I also have a cup holder on the stroller, so was able to stick our passports and my phone in it for ease of access. I travelled with West Jet and did not purchase an extra seat for Dax. I would have, but I checked with the airline before we left and the plane was pretty empty. If you can afford to book a seat for your baby, I would! West Jet's policy is to only allow a car seat on the plane if you purchase a seat, so on our way to Maui I checked the car seat at the gate. On our way home though, I asked realllllly nicely at the check-in counter and they let me take the car seat on the plane. Both flights, we had an entire row to ourselves, which made it SO much easier than having him sit on my lap the whole way (6+ hours of flying). But if I were to do it again, I would buy the seat and have the car seat for both flights. Bring a travel bag for the stroller so it doesn't get scratched. If it does get damaged, you can contact the airline and they will replace.

Book smart flights. I booked non-stop flights both ways to Maui. If you can do this and avoid layovers, this will be much easier! Our flight there was during the day on the way there and overnight on the way home. The red eye flight was MUCH better. If you can fly overnight, do it! Our daytime flight was okay, but Dax had trouble sleeping with the plane lights and noises and I had to entertain him for 6 hours. On our way home, he slept the entire way in his car seat and I slept too! Also, the time of day you are flying is important for daytime flights. If your baby is fussy in the evenings, chances are they will be fussy on an evening flight. Try to book them during your baby's best times awake.

Pack smart. In Dax's diaper bag on the plane, I made sure I had extra formula, pre-filled bottles with distilled water (they will heat it for you on the plane and you're allowed to bring liquids and food for baby through security just make sure they are in a ziploc), lots of snacks (not messy ones, I had orange puree all over my shirt and pants when we landed), extra diapers, bibs, two sleepers (easiest to put baby in a sleeper for travelling) and lots of toys. I brought toys that I know keep Dax occupied and a couple new ones for him. I had everything in large ziploc bags, so it was easy to find things in a pinch. I needed an extra sleeper on the way home as when we landed Dax spit up all over himself and then had a blow out diaper, so I was really happy to have a change of clothes for him when we landed. Keep in mind during the day, the plane gets VERY hot, so Dax was in his diaper for most of the flight. I held him for one of his naps and got super hot, so make sure you have layers. On the flight home it was overnight, so it was cold. Make sure you have a couple blankets and layers for yourself.

Try to feed during landing and take-off, but don't stress if you can't get your little one to latch or take a bottle. I read this tip over and over on other blogs and was really worried about Dax's ears. He refused to eat during both take off and landing and was fine! Every baby is different, so try but don't worry if you can't as it isn't in your control.

ASK for help BEFORE you need it. I asked the flight attendants to carry everything on the plane for me. I asked the people in front of me (who happened to be moms) to hold Dax when I had to go to the bathroom. I asked people in the security line to clip the car seat into the stroller. I asked the security officer to help with the stroller when we went through screening too. People are usually willing to help. Don't wait until you are stressed and have a crying baby to ask people for help.

It won't be as bad as you think it will be. Just anticipate everything that you deal with at home and you will be fine. Think about everything you need at home and bring it. I didn't pack enough formula, diapers or wipes, so ended up having to purchase extras in Maui. They were almost double the price there, so if you have room in your suitcase, then bring more than you think you will need.