We usually try to push Everett's nap so he will sleep on the plane (best white noise machine ever) but when that doesn't work I thought I would let you know what I have learned so far...I have only had one bad experience with a rude passenger, people are usually so nice and understanding.
NEW TOYS: Before the airport I hit up the Target Dollar Spot and just grab a few things that Everett has never seen before. It doesn't have to be an awesome toy, as long as it is new it entertains him for a while. When he was a wee babe, the stacking cups were a favorite and now he is really into sticker books (which are a good time suck) Someone also just recommended pipe cleaners to me which I am going to try on this next flight, I think I will bring some Cheerios and show him how to string them onto the pipe cleaners (again, I love things that take a LONG time)
BOPPY: We have only done one red-eye flight (which I will probably never do again) but I brought my Boppy breastfeeding pillow, so Everett could lay down on it when he was asleep on one of our laps. That way no one's arms are going completely numb holding him.
SNACKS: Obviously super important for all ages. When he was a baby we loved bringing the squeeze pouches and puffs and now he loves goldfish (can I just say the new goldfish flavors are freaking delicious) and fruit snacks etc. I know suckers can be sticky but they also take a lot of time to eat and are kind of a novelty to Everett so it might be worth it (and good for popping their little ears). Also, just saw on the Love Taza blog that her kids love Pez on flights so I will have to try that as well.
ICE CUP: When the flight attendants come around with drinks I ask for a cup with just ice. It might just be Everett, but he loves Ice so I let him suck on the ice and play with it for a bit and that will entertain him for at least 10-15 minutes.
BABY CARRIER: Everett is just barely to big for our carrier these days but up until now it was a life saver going through airports. I would strap him in so I could be hands free at the ticket counter and through security and I could still pull my own carry on. Be careful with the sling carriers that have metal rings, I have seen security make moms take them off and wake up sleeping babies to go through the scanner!
BOTTLE/SIPPY/SOOTHER: This is old news but bring them a soother or some kind of liquid or breastfeed on take-off and landing to help their ears pressurize. You are allowed to bring breast milk, formula, or even juice or water through security if it is in a baby cup they just test it real quick. NOTE: You do not need to wake up your baby if they are sleeping to make them suck or anything. I learned that the hard way.
WINDOW SEAT: I always try to get a window seat because A)It's the easiest to breastfeed modestly and B) Everett loves pulling the shade up and down and looking out the window. On flights where I can't select my seat, I usually ask at either the initial ticket counter or the gate and every single time they have been able to change my seat to a window seat.
IPAD: I use this as last resort but Everett will watch a little bit of a downloaded movie or Barney for about 10 minutes. We also love to scroll through photos and videos I have on there and point out who is in the pictures and what we were doing. Also Photobooth and simple games can be entertaining for when they are a little older.
CHECK IT: Do you know almost all airlines allow you to check a stroller and car seat and base for free. You can also carry on a diaper bag and breast pump for free (in addition to your own carry on) for FREE! We usually check our car seat (in this awesome travel bag) and then gate-check our stroller so we can put him in in through the airport (when we aren't using the bjorn).