This is a compilation of commercials from the 1990s, recorded on VHS tapes from CBS 2 Chicago (WBBM-TV), NBC 5 Chicago (WMAQ-TV), and ABC 7 Chicago (WLS-TV).
The early ABC promos were from like 1994, then a WLS-TV ID later on was from no earlier than '96. The "Mutiny" NBC TV movie aired in '99, so the spots are from all across the decade, as the title suggests.