I fly AA once a month. It doesn't pay for me to buy a monthly subscription. Would be great if AA offered a 10 pack at a discount to be used over 6 months or a year. AA would get the cash up front and would increase the amount of customers who use the paid service.
I use the Southwest Business Chase card. For $200 annual fee, I get free wifi on Southwest. Citi or Barclays should offer a credit card product with it included.