Sutcliffe won 31 games over the course of the next two seasons for Cleveland and led the American League in earned run average in 1982. In mid-1984, Cleveland traded a struggling Sutcliffe to the Chicago Cubs for Mel Hall and Joe Carter. Sutcliffe rebounded and won 16 games for the Cubs while losing only one, helping them to the division championship. On October 2, 1984, he started the first game of the NLCS against the San Diego Padres, giving up two hits and no runs, not only gaining the victory, but also hitting a home run in the third inning. Five days later, Sutcliffe pitched the final game of the series at Jack Murphy Stadium, but posted the loss after giving up four runs in the seventh inning.
Rick won the Cy Young Award with a unanimous vote, beating out Dwight Gooden and Bruce Sutter. He also finished fourth in the league MVP voting. When he re-signed with the Cubs as a free agent the following year, his contract briefly made him the highest-paid pitcher in baseball.
Sutcliffe started the 1985 season strong, going 5-3 in his first eight starts, including two complete game shutouts. A hamstring pull on May 19, limited his starts for the year, followed by a series of arm injuries limited Sutcliffe's effectiveness over the next two seasons. In 1987, he bounced back to win 18 games and finished second in the league's Cy Young voting to Steve Bedrosian despite playing for a last-place Cubs team which featured National League Most Valuable PlayerAndre Dawson.
On July 29, 1988 in Philadelphia, Rick achieved one of baseball's rarest feats, especially for a pitcher by stealing home plate during an 8-3 win over the Phillies, in which he also notched the victory. In 1989, Sutcliffe won 16 games and made his final All-Star appearance, where he was managed once again by Tommy Lasorda. He also helped the Cubs to another division title, but the Cubs lost to the San Francisco Giants in the playoffs.
Recurring arm injuries caused Sutcliffe to miss most of the 1990 and 1991 seasons and the Cubs did not offer him a contract for the next season. Signing with the Baltimore Orioles, Sutcliffe went 16–15 and 10–10 in 1992 and 1993, starting the first game at Oriole Park at Camden Yards. He wound up his career with the St. Louis Cardinals in 1994, going 6-4 in an injury-plagued season. He retired with a career record of 171–139, with an ERA of 4.08. He holds the unique distinction of having won each of the following league awards, once each, and each in a different season: Rookie of the Year (1979), Cy Young Award (1984), ERA leader (1982), and wins leader (1987).
On March 13, 2008, Sutcliffe was diagnosed with "curable and maintainable" colon cancer. He underwent chemotherapy and radiation treatments in his hometown of Kansas City during the spring of 2008 and returned to work with ESPN on May 21, 2008. He continues to maintain a positive attitude and credits this to his faith in Jesus, strong family encouragement, incredible friends and immense support all over the world. As a result of his trials, he has shown great interest in motivational speaking about overcoming trials through your faith for groups such as Fellowship of Christian Athletes.