Amateur Minor hockey Chychrun started playing hockey in his home state of Florida with the Junior Everblades and the Florida Jr. Panthers organizations. When Chychrun was 13, he joined the Little Caesars hockey organization in
Detroit, Michigan, where he played very well during his major bantam season. At the time, he continued living and practising in Florida, travelling to Michigan on the weekends to play. The following season he remained with Little Caesars, playing for their U16 team. In 2013, Chychrun was drafted by the
Youngstown Phantoms in the USHL draft.
USA Hockey implemented a rule requiring 15-year-old players to receive a special exemption to play junior hockey. Chychrun applied for one but was denied. As a result, Chychrun played his minor midget season for the Toronto Jr. Canadiens in the
Greater Toronto Hockey League.
Major junior . Following his outstanding GTHL season, Chychrun was selected first overall by the
Sarnia Sting in the 2014 OHL Priority Selection. He played 12 games with the Sting during the
2014–15 season before suffering a shoulder injury. He subsequently missed eight weeks, including the 2014 World Under-17 Hockey Challenge, before returning to the lineup on December 19. Upon returning from his injury, Chychrun tallied five goals and ten points through his first eight games. Despite missing 22 games, Chychrun quickly tallied 22 points in 26 games played to rank in the 13 in OHL Rookie scoring by February 3. He finished the season with 16 goals and 33 points through 42 games to earn nominations for the
Emms Family Award, the
Max Kaminsky Trophy, and the
Red Tilson Trophy. He was also voted onto the 2014-15 OHL All-Rookie First Team. He earned these honours despite missing the final 26 games of the regular season and the OHL 2015 playoffs because of an upper-body injury. By October 21, Chychrun had registered one goal, five assists, and a plus-6 rating through his first 10 games and was selected to participate in the 2015 CHL Canada-Russia Series. He was eventually drafted by the
Arizona Coyotes in the first round, sixteenth overall. This was far lower than expected; prior to the start of the
2015–16 season, Chychrun was regarded as a top three selection.
Professional Arizona Coyotes On July 30, 2016, Chychrun concluded his OHL career and signed a three-year, NHL entry-level contract with the Coyotes. Following the signing, he was one of 29 prospects who participated in the Coyotes 2016–17 Rookie Camp at
Gila River Arena. After impressing at the rookie camp, he participated in the Coyotes preseason. During his first two preseason games, he averaged 22 minutes of ice time and played a physical game while also tallying points. Due to his impressive play, Chychrun subsequently became the youngest player in Coyotes history to make his NHL debut with the team at 18 years and 198 days. As a result of his age, Chychrun would not be eligible to play in the
American Hockey League (AHL) for the
2016–17 season if the Coyotes wished to move him. He tallied his first career NHL point, an assist, in his debut game to lift the Coyotes to a 4–3 win over the
Philadelphia Flyers. After playing 12:09 in the season opener, he was a healthy scratch for the second game. Chychrun later scored his first NHL goal on October 20, 2016, against
Carey Price of the
Montreal Canadiens. He finished the month of October with one goal and two assists through his first seven NHL games. In December, Chychrun missed one game due to an upper-body injury but played 17:23 in his return to the lineup on December 27. Chychrun continued to be made a healthy scratch throughout the season and he sat out four consecutive games in early to mid-February. Following these scratches, he improved offensively and notched a goal and two assists for his first three-point game on March 11. This increased his points tally to six goals in 54 games and ranked him second among first-year defensemen. He later scored his seventh goal of the season on March 16 to extend the Coyotes points streak to five games. Chychrun finished his rookie season tied for second among first-year NHL defensemen with seven goals and seventh for points with 20. He subsequently became the first Coyotes rookie defenseman since 2005–06 to score this many points, which was also the third highest by a rookie defenseman in team history. He also ranked fifth on the team with 99 blocked shots. Following the surgery, he went to
Philadelphia for rehabbing and returned to skating and full practice in mid-October. Despite this, he was assigned to the Coyotes' AHL affiliate, the
Tucson Roadrunners for conditioning purposes on November 28. He made his NHL season debut that night, scoring a goal in 22:40 minutes of ice time in a 3–2 loss to the
Vegas Golden Knights. Chychrun subsequently tallied four goals and 10 assists through 50 games while averaging 20:15 of ice time. His season was cut short again after he was ruled out for the remainder of the season on April 4 after suffering a
torn ACL. in 2019 Chychrun underwent surgery to repair his torn ACL in the 2018 off-season but was ruled eligible to play for the
2018–19 season. Prior to his season debut on November 13, the Coyotes signed Chychrun to a six-year contract extension. However, his return was shortlived as he suffered another upper-body injury before his second game of the season. Chychrun scored an assist in his return to the lineup on November 21 as the Coyotes fell to the Golden Knights in overtime. He also missed four more games in late January and early February due to a lower-body injury. Despite missing 22 games, Chychrun ranked fourth among Arizona defensemen with 11 points by February 9. As the season continued, Chychrun served as a healthy scratch for numerous games. He finished the season tying his career high with 20 points through 53 games as the Coyotes failed to qualify for the
2019 Stanley Cup playoffs. During the 2019 off-season, Chychrun spent one month in Florida and then the rest of the summer at a cottage just outside of Ottawa. As he was battling tendinitis in his knee, he took off a month to let it recover before starting training. He played in his 200th career NHL game in a 4–2 win over the
Columbus Blue Jackets on December 3. The team continued to improve and they climbed to the top of the Pacific Division in early December with 38 points. By February 11, Chychrun had maintained a career-best four game point streak and tied for fifth on the team in goals scored. He also ranked eighth among NHL defenseman in goals scored with 12 and tied for second in power play goals scored with five. This quickly accumulated into seven points through eight games in February before he suffered a lower-body injury on February 20. He subsequently missed seven games before the NHL paused play due to the
COVID-19 pandemic. At the time of the pause, Chychrun had tallied a career-high 12 goals and 26 points through 63 games. When the season resumed, Chychrun was healthy enough to join the Coyotes for the
2020 Stanley Cup Qualifiers against the
Nashville Predators. Chychrun made his NHL postseason debut in Game 1 as the Coyotes beat the Predators 4–3. The Coyotes swept the Predators in four games to advance to the Western Conference Quarterfinals against the
Colorado Avalanche. The Coyotes were eventually eliminated by the Avalanche in five games. For the second straight season, Chychrun was named to the Coyotes opening night roster as a healthy player. Chychrun began the season strong, registering four multi-point games by February 22 to rank second in scoring among West Division defensemen with 13 points. By March 9, he had tallied his seventh goal of the season to rank third among NHL defensemen across the league. Later that month, he became the second youngest defenseman in Coyotes history to record 100 points with the team. On April 4, Chychrun scored his first career
hat trick in a 3–2 overtime victory against the
Anaheim Ducks. He thus became the third defenseman in NHL history to score all three of his team's goals with the third coming in overtime. After adding two assists the following game, Chychrun set a new single season, career-high in points with 27. Later in April, he led all NHL defensemen with 14 goals, one more than
Darnell Nurse of the
Edmonton Oilers. Chychrun finished the season leading all defensemen with 18 goals and tied for 10th in points in 56 games. He finished 10th in the
James Norris Memorial Trophy voting, an award given to the league’s best defenseman.
Ottawa Senators scoring on
Philipp Grubauer of the
Seattle Kraken in 2023 On March 1, 2023, the Coyotes traded Chychrun to the
Ottawa Senators in exchange for a conditional first-round pick in the
2023 NHL entry draft, a conditional second-round pick in the
2024 NHL entry draft, and a second-round pick in the
2026 NHL entry draft. On March 25 in a game against the Tampa Bay Lightning, Chychrun was injured falling into the boards. Initially, it was thought he would miss only a couple of weeks, but ended up missing the rest of the season. In his first full year with the Senators, Chychrun scored 14 goals and 41 points, matching his career high. He played in all 82 games for Ottawa, leading all of the Senators' defensemen in scoring.
Washington Capitals On July 1, 2024, the Senators traded Chychrun to the
Washington Capitals in exchange for defenseman
Nick Jensen and a third-round pick in the 2026 NHL entry draft. He scored his first goal in a Capitals uniform in the following game, a 4–2 victory over the Vegas Golden Knights on October 15. He missed time at the end of October and early November after suffering an upper body injury in a game versus the
New York Rangers on October 29. He was placed on injured reserve on November 2. He returned on November 9 and recorded a three-point game on November 25 in a 4–1 win over the Florida Panthers, scoring the game-winning goal and adding two assists. On March 25, 2025, Chychrun agreed to an eight-year, $72 million contract extension with the Capitals, carrying an average annual value of $9 million. ==International play==