in 1983 Piedmont had a $600 30 day pass. I flew almost every day many flights each day. I never totaled it but it had to be close to 100,000. I was collecting bumps on a summer break from college.
I've also met european students in youth hostels doing some pretty insane schedules when delta had a 30 day standby pass for foreign students.
Off topic I would give an honorable mention to the Russian Astronaut Polyakov in the Mir LD-4 he spent 437.7 days