Hi!
I have traveled with my children a lot! I also work for JetBlue. By the time my daughter was four, she had been on 36 different airplanes. It can be very hard, but I think it is an experience that will make you stronger.
The take-offs and landings always hurt their ears. They still even hurt my ears sometimes. You should give the baby tylenol about a half an hour before the flight takes off. This will alleviate some of the pain. If the baby is awake, you should have him drinking a bottle or sucking on a pacifier during take-offs and landings as well. This helps with the pressure in the ears.
I don't know what airline you are flying on, but security is the same for everyone. When going through security, the adults and older children are not allowed to have any liquid. Each person is allowed one quart-size baggie to put your liquids, gels, or pastes in and each container cannot be larger than 3.4 oz. The baby, on the other hand, is allowed whatever you need for him, and it does not have to be in a baggie. I would suggest having a couple of bottles pre-made so that you don't have to worry about mixing anything. You can also take baby food, diaper ointment, wipes, etc. Anything necessary for the baby is ok.
One last thing that I highly recommend:
Take a change of clothes for the baby and yourself ON the plane. I had an incident once of an explosive diaper after we got to the gate and my luggage was already under the plane. It was the stinkiest, most miserable 5 1/2 hour flight of my life!! Good luck!
If you have any more questions, you should call the airline. With Jet Blue, if you are taking the baby as a lap child, the baby is allowed a car seat, a stroller, and a diaper bag on top of all the luggage that you are allowed. You might want to call and find out if this is the case for you, so that you don't have to worry about cramming everything into fewer suitcases so that you have allowances for the necessities.
Cori