Buy it on an AS flight using the BofA Alaska credit card which gives you a 20% rebate on Alaska onboard purchases. Cancel the subscription anytime during the month (you'll still be able to use it until the end of the subscription month) and on your next AS flight after it expires, buy it again. Rinse and repeat. If you let it auto-renew, I don't believe the renewal gets the 20% rebate since the renewal is charged by Gogo rather than Alaska. The 20% rebate is worth $9.99 against the current $49.95 monthly subscription fee. You get additional savings, depending on how often you fly, in that you usually pay the next fee later than exactly one month.