Would this be related to DNS?
Pay the signup charge, and also stand up a wifi network. Call it "Foo discounted" if the plane's SSID is "Foo". Put up a captive portal that lets the user claim various "discounts", like veteran, senior, child, etc. No matter what they choose, charge them $2 via a payment page. Once you've been made whole on the service cost, future visitors get a notice that "all discounts have been claimed, please use Foo".
Now you have free internet and all those using your router/portal have $2 internet. The upstream bandwidth is certainly atrocious so you will easily be able to multiplex all the data onto your connection.
Bundle it into a RPi kind of device (has to look finished, like a music player or smth, to get past security) so that you can continue to operate the device even when tray tables have to go up, when you go to the bathroom, etc.
I find it extremely doubtful that the airplane has WIPS or WIDS that will deassociate connections to your rogue wifi. And after all, are you not allowed to have a LAN party?
Someone smart created a TCP-over-DNS tunneling tool that I had a lot of great experience with, at least for more simple news websites of the day.
Like have a WhatsApp relay set up at home that you are sending messages to and from, from the plane.
Like at a most basic level, send a message of a URL to your home WhatsApp which loads the web page there, and sends the HTML back as a WhatApp message reply so you can render it etc.
Wonder what someone could all do and make work.
edit Guess someone made a TCP relay using WhatApp already, neat.