In 1994, he signed as a free agent with the Chicago Bears, and spent the next five years with the club. In his two full seasons as a starter (1995 and 1997), he was highly productive and passed for over 3,000 yards. Kramer currently holds the Bears' single-season record for passing yards (3,838) and touchdown passes (29), and attempts in a single game with 60 on November 16, 1997. Kramer signed with the San Diego Chargers in the 1999 offseason, but retired midseason due to a neck injury. Though he also missed much of the 1996 season with a neck injury, the two injuries were unrelated.