GI Bill Planning Act of 2019 This bill extends or removes specified deadlines for certain Department of Veterans Affairs (VA) education benefits. Specifically, the bill updates the Montgomery GI Bill program by extending the period of time under which an election must be made for entitlement to educational assistance under the program. The bill phases the program out on September 30, 2029. The bill also removes a deadline that prevents certain veterans from receiving in-state tuition, regardless of their state of residence, using VA education benefits at public institutions of higher education. Currently, a veteran who is discharged or released after at least 90 days of active service must be within three years of their discharge from active duty to receive in-state tuition (regardless of their state of residence). The VA must post on a public VA website a database explaining any requirements established by a public institution of higher learning for an individual to be charged in-state tuition. The VA must disapprove a course of education at a public institution of higher education that does not provide the VA with an explanation of the requirements (or a timely update of such requirements) for an individual to be charged in-state tuition.