After being drafted by the Montreal Canadiens in 1981, Chelios enjoyed two strong years at the University of Wisconsin. As one of the top collegiate players in the country, he was selected to play for the United States at the 1981-82 World Junior Championships. Following the 1982-83 season he was named to the WCHA Second All-Star Team and the NCAA Championship All-Tournament Team. Realizing a dream to play in the Olympics, Chelios postponed his NHL debut and committed to the U.S. national team program for most of 1983-84. The defending gold medallists from 1980 in Lake Placid disappointed with a seventh-place finish but the robust blueliner was one of the few bright lights for his country.
Chelios arrived in Montreal, in time to play the last 12 regular-season games of the 1983-84 season. In the regular season, the Habs finished well behind their first-round opponent, the Boston Bruins. Chelios's second-period goal in the 1-0 opening game victory paved the way for an upset. The squad reached the semifinals that year, where they gave the New York Islanders all they could handle. That fall, the young Chelios was selected to play for the United States again, this time at the Canada Cup.
During his full rookie season the following year, Chelios racked up 55 assists and played in all situations for Montreal. He finished as a runner-up in the Calder Trophy voting to Mario Lemieux. Chelios's 64 points set a new Canadiens record for a first-year blueliner. In 1985-86 he missed nearly the half the season through injury, then played superbly in the Habs' run to the Stanley Cup.
Chelios added to his international experience by playing with the NHL All-Stars against their Soviet counterparts at Rendez-vous '87 in Quebec City and by appearing in his second Canada Cup for the U.S. that same fall. In 1987-88 he hit the 20-goal mark for the first time while emerging as one of the elite NHL blueliners.
The 1988-89 season was rewarding in individual and team accomplishments. The Canadiens reached 115 points, their best performance since winning the Stanley Cup four straight times 10 years earlier. Chelios was singled out for his play by winning the Norris Trophy and being selected to the NHL First All-Star Team. The following year started well when he was named co-captain with Guy Carbonneau, the first American so honored in a Habs uniform. Unfortunately, he battled injuries and inconsistency all year, and the team was knocked out by Boston in the Adams Division final.
Montreal traded Chelios to Chicago to acquire local hero Denis Savard prior to the 1990-91 season. Chelios responded with 64 points while helping the Hawks finish at the top of the NHL standings for the first time since 1967. Chelios and Steve Smith formed one of the toughest defense tandems in hockey and became crowd favorites.
The hometown favorite went on to play nine seasons in Chicago reaching the Stanley Cup finals in 1992 loosing in four straight games to the defending champions from Pittsburgh. Chelios would capture his second Norris Trophy in 1993 and capture a third in 1996 before representing his country for a second time at the 1998 Winter Olympics in Nagano, Japan.
After beginning the 1998-99 season with Chicago, Chelios was dealt to the Detroit Red Wings who were looking to bolster their blueline and make a run for their third straight Stanley Cup. Unfortunately, Chelios and the Wings fell short in their attempt, however, three years later Chelios would capture his second Stanley Cup and was a instrumental part of the U.S. Silver Medal at the 2002 Winter Olympics in Salt Lake City, Utah.
A tireless worker and one of the most fit players in the NHL, Chelios began his 20th NHL season in 2002-03 and showed no signs of slowing down once the 2003-04 season had concluded. Despite the Red Wings second round exit from the playoffs, Chelios who had reached the 900-point plateau during the regular seson, was named to his second World Cup team in the summer of 2004.
During the lock out in 2004-05, Chelios signed with Motor City (UHL) as a free agent and competed in 23 games. The following season Chelios returned to the NHL with the Detroit Red Wings and was a member of Team USA during the 2006 Olympics in Turin. After appearing in 71 games of the 2006-07 season, Chelios returned to the Red Wings for yet another NHL season. Through 69 games in Detroit, Chelios was a plus 11 and during a March 20, 2008 game against Nashville he became the second-oldest player in NHL history to score a goal. In the following playoffs, Chelios laced his up his skates for 14 games and helped the Red Wings capture their fourth Stanley Cup in eleven seasons.
In 2009-10, Chelios was back in the NHL, this time as a member of the Atlanta Thrashers, playing with teenagers like Zach Bogosian and Evander Kane, both of whom are almost thirty years younger that the veteran defenseman.
On August 31, 2010, at the age of 48, Chelios announced his retirement, ending a decorated career that included three Norris Trophy wins and three Stanley Cup championships.