When booking a cross country or international flight it can be very tempting to book a connecting flight due to it usually being cheaper. If flying alone it's something I consider depending on how large the savings are but when flying with kids unless flying non-stop will seriously break the bank I avoid connecting flights like the plague!! Here's why:
You Only Have to Board/Get Settled Once
In my opinion getting on the plane is the hardest part! You've lugged all your crap, got settled, your kids are entertained, behaving themselves, or even fast asleep. Things are going so smoothly but now it's time to land because you have a connecting flight. Now you have to clean up, get all your stuff organized, God forbid wake the kids up from their sleep and then make your way to another gate to start over and hope they fall back asleep. Boarding and deboarding is my least favorite aspect of flying with kids so I try to limit this to only once.
Avoid Going Through Customs Twice
If you are flying international with a layover in a foreign country you will have to go through customs in the first country you land in and then again in the country of your final destination. Remember you will have to collect your bags* (strollers, car seats, etc. included) and get them to where your airline rechecks them which could be close to customs but it could not. If you are flying alone with your child and had help from the person who dropped you off to the airport they won't be around to help you now so you will be responsible for all of your belongings.
*Countries apart of the EU has different rules
Avoid Getting Stuck In Your Layover City
If your 1st flight gets delayed enough you could miss your connecting flight and if it was the last flight of the night you could be stuck in that city. Depending on the reason for your delay the airline may or may not provide a hotel for you. If they don't your options are to sleep at the airport- imagine doing that with kids or pay for a hotel on your own, one you didn't budget for. Even if they do provide a hotel you have to leave the airport, possibly manouver a city your are unfamiliar with and then come back in the morning and go through security all over again. This actually happened to us when we went to Australia except our flight was cancelled and when I tell you it was a pain dealing with the airline to give us our hotel voucher, get a shuttle to the hotel (I didn't fly with our car seat because you can't use US car seats in Aussie and the airline, United, didn't provide one for us), and then wait on line for 45mins to check in because the entire flight was sent to that hotel. The flight was cancelled at 12:30AM and we didn't get to our room until 3AM. Luckily I only had Kennedy who was 8 months at the time so she slept in the carrier but imagine if I have Jordyn how cranky she would be, shoot I was cranky as hell as an adult.
There are many instances where flying non-stop is just not feasible, some destintions you don't even have the option. If a non-stop flight is not possible here are my tips on making a layover with kids easier.
If You Can't Do Non-Stop At Least Do Direct
This is where you don't change planes in the layover city, some passengers just get off and new ones get on. Southwest has a lot of these types of flights.
Have Your Connection in the US If Possible
When departing from the US: Your bags will go to your connecting flight automatically and you won't have to collect them to go through customs.
When arriving to the US: You will clear customs in the first airport you arrive from abroad. You will collect your bags here and re-check them to your final destination. You will not have to clear customs upon arrival to your final destination.
Make Sure Your Layover is Long Enough
If you do have a layover a short one like 30 minutes one will not cut it with kids. This leaves no wiggle room if your 1st flight is delayed. Even if it did land on time just imagine your connection is in SFO or ATL and your next flight is 3 terminals away. You gate checked your car seat or stroller and now have to wait for it to come. Sometimes I am in the first few rows but still every one has deboarded (is that a word) and I still haven't collected the car seat because it takes that long for the staff to bring it. That alone could eat up most of your connection time. Now you still have to manuever through potential crowds at the airport with your child who is so tired and won't walk or your weaving your stroller in and out of people to run as fast as you can to catch your plane that leaves in 10mins. Even if you're traveling with an infant and using a carrier and don't have a stroller to deal with you still can't run as fast with the baby, believe me I tried one time when my 1st flight was delayed 2hrs and we landed 15mins before our connection was scheduled to leave.
Be Conscious Of When Your Connection Lands
There are many connecting flights that land at 2 or 3AM and then you have to wait 2-3hrs for your next flight. As an adult I would be grumpy as hell, just imagine adding kids to that mix- avoid this scenario at all costs.
Don't Sit Still During Your Layover
Use this time to walk around with your little ones and get all of their energy out. Before flying see if your connecting airport has a kids play area and write down the location. Eat a good meal and/or buy more snacks for your second leg if you need to or anything else you realized you may have forgotten.