Talk to me about flying with an 18-24 month old

BIL is getting married in CA this summer and I just started looking at flights to get an idea of times and prices. DS will be about 20 months when we go. We live in CT, but we'll probably fly out of NY since I want to take a direct flight. I really don't want to pay for an additional seat for DS. I'm sure things will be different by the summer, but right now, he'd probably prefer sitting in my lap than next to me.

How old was DC when you flew?
How long was the flight?
Did DC sit on your lap? If so, how did that work out?
I can't even imagine how much of a PITA it's going to be to bring a car seat, stroller and large suitcases. As hard as I try, I totally overpack. Plus, we're going for 9 or 10 days. Is it really that bad dealing with everything?
Any tips on time of day to fly, how to fly with a toddler, etc?

Also, we'll be renting a house there with DH's siblings. I do not want to bring a PNP in addition to everything else. Besides putting DS in bed with us, are there any lightweight travel bed options that we could get?

TIA for your help!

Re: Talk to me about flying with an 18-24 month old

DS was 17 months old on his first airplane trip to St John

I booked an early flight so he would take a nap for most of the time. I bought him a separate seat and I brought the car seat. It was well worth it and hands down would totally do that for a trip to Cali

The hotel had a portable crib so I brought my own sheets etc

I used a bottle to help his ears for take off

Direct flight is much better--we switched flights on way home and it was crazy

Bring a tote bag of things to do on the plane (coloring, flashcards) and we brought a portable DVD player