Although the station's need for a second exit was rated as a high priority in 2004, Chester was the last station left on the east end of Line 2 Bloor–Danforth where design work and consultation on the addition of a second exit had not started. In May 2014, a list of 15 potential second-exit sites was developed. In June 2016, the location of the second exit was announced, situated at the west side of the parking lot across the street from the main entrance. The construction of two elevators and the second exit started in 2018, and the elevators opened on September 2, 2020; the second exit is expected to open in 2021. As part of the accessibility upgrades, the station was closed for two weeks in June 2020.