Having been displaced by Al Spohrer as the Braves' starting catcher early in the 1929 season, Taylor's contract was sold to the Chicago Cubs for the waiver price of $7,500 in July after all the other teams in both the American and National Leagues had passed on him. When the Cubs' future Hall of Fame catcher Gabby Hartnett suffered an arm injury early in 1929, Taylor filled in capably, helping the Cubs win the National League pennant. He helped guide the Cubs' pitching staff to a league-leading 14 shutouts and finish second in team earned run average and strikeouts. In the only postseason appearance of his career in the 1929 World Series against the Philadelphia Athletics, Taylor made only three hits but was cited as an unsung hero in a losing cause for the Cubs because of his consistent, unwavering defensive skills behind the plate. When Hartnett returned from his injury in 1930, Taylor went back to being the Cubs' backup catcher. In 1932, Cub manager Rogers Hornsby credited Taylor with helping develop the skills of Lon Warneke, as the young pitcher led the league with 22 wins.