Chicago Cubs Playoff History | 1885 - 2026 Chicago Cubs History Overview The Chicago Cubs have played a total of 142 seasons Their first season was in 1885, and their most recent season was in 2026 Have the Chicago Cubs gone by any other names? Yes Between 1885 and 1889, the team was known as the Chicago White Stockings In 1890, the team changed their name to the Chicago Colts