People say this might be glitched but I unlocked it no issues. What I did though was to listen to at least one full song from start to end in each of the station until there is a commercial and listened to two chat stations again until there is a commercial. The achievement unlocked when left my car, having finished listening to 2 minutes to midnight in Vrock (as soon as the song ended and a commercial started). I think the unlock condition may be listening to a full song and triggering a commercial in each of the station.
Edit:Thanks to Tozi for confirming that this doesn’t have to be done in one sitting
Edit 2: Per some comments after new update the achievement unlocks after listening to each station for 5 minutes