We took a portable DVD player & he watched a movie & fell asleep(if you aren't happy for him to watch TV then I'm no help at all), we also took a little magnadoodle and few books and snacks - those Bellamy dried apples were a hit.
Take him for a walk up the aisle a few times to stretch his legs. Hope you have a good trip!
He'll probably do much better than you think ... the imagining is far, far worse than the reality - at least that was my experience .
I flew without DH (3hr flight) when DS1 was 25 months and DS2 4 months. At 27months your DS will be in a seat of his own, so use it to your advantage. He'll have a tray table to use! I bought a couple of new sticker books and books on things that my DS1 liked (trucks, farm animals) plus a couple of new toys. I didn't spend much money, just a few new things that would help hold his interest. That kept him amused for a while, but what really worked a treat for me was buying him some pringles (chips etc are a rare treat here). He ate them most of the way! He really was as good as gold - although he'd flown before he was more aware of things around him at that age. He was a little concerned about what was going on during take off and landing, but I put my arm around him and talked to him about what was happening. And we looked out the window too, which fascinated him once we were in the air.
Pack lots of snacks, any small favourite books or maybe some small toys that he hasnt seen before that might keep his interest. If you get a window seat you can point to everything outside. Good luck!
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