My DD (almost 4) has frequent flier cards on two airlines, simply because,
with no local family and relatives all over the USA, plus DH and I both
travelling at least once a year on business (and, so far, it's worked that
the other spouse and child can come along), she's flown 4-6 round trips
every year since she was born.


The biggest help, if we can get it, is to have a suite, not a hotel room. If
we can have a separate sitting room and bedroom (with her sleeping in the
sitting room-pull out couches are great for her since they're lower to the
ground than most hotel beds, as are rollaways), she sleeps well and it
works wonderfully, or, when we travel with my parents, as we do a couple
times a year, get two rooms that connect.

In both cases, this allows her to sleep while it allows the adults to not
have to be on a preschooler's schedule.

If we have a regular hotel room, pretty much everyone has to sleep on her
schedule, because she needs it dark and with few distractions to initially
get to sleep, and that doesn't happen in a hotel room with other people.
Once she's out, turning on a reading light is possible.

I've also been known to take a book out in the hallway, make the hotel room
dark, and leave the door open a crack so I can hear her, especially for
afternoon naps.

On air travel, she's got the security stuff down to a science. I will
forever be grateful to the TSA agent who, on one of her first flights when
she was old enough to go through the security gate on her own, asked her if
he could look at Draggy's "bones" on the monitor, and then turned the
monitor so she could see (after going through the gate herself) what her
dragon and bag looked like as he scanned them. Since then, she's handled it
herself fine, putting her shoes, backpack, and draggy up for scanning,
walking through, and getting her things on the other side. We take her car
seat with us, since she still uses a 5 point booster which is legal for
airline travel. She's more comfortable in it, and she can see out the
window, and we need it when we get there anyway.

We let her pack her own backpack of toys and activities, plus I make sure
she has a few new books, a new coloring/activity book (dot to dots are the
favorite now), crayons/markers and a couple of little new things for the
trip (I stock up on small seasonal toys after holidays for this purpose.
I've still got a few from last Easter in our closet). This is usually enough
for the flight and a relatively limited amount of time spent in the hotel
(and usually she ends up collecting a "treasure" or two on the trip anyway).

Even at her current age, we do still take the stroller on trips, although we
don't use it in the airport, and the only place I use it at home is the zoo.
A lot of the places we go end up having a lot of walking, and having the
option to NOT carry her is very nice.