Amateur Darling grew up in
Chicago's southern suburb of
Lemont, Illinois, and as a child idolized the
Chicago Blackhawks goaltender
Ed Belfour. He played
minor ice hockey with the AA Vikings (Orland Park), AA Huskies (then Darien, now Romeoville) and AAA Team Illinois and Chicago Young Americans. He played in the 2002
Quebec International Pee-Wee Hockey Tournament with the Chicago Young Americans. He attended Notre Dame College in
Wilcox, Saskatchewan, in eighth grade and played AAA hockey for the Hounds. He attended Lemont High School. At the University of Maine, he was involved in excessive partying and by his sophomore year was abusing alcohol. He frequently violated the school's code of conduct and was given three suspensions from the hockey team within a 16-month period, resulting in him being dropped.
Minor leagues After bouncing around for several years through various minor hockey leagues, his goaltender coach Brian Daccord said he was not permitted to play at his hockey school until he made a dedicated commitment to the gym. It was at this time, he lost nearly 40 pounds and gave up alcohol in 2011. Darling said even at the lowest point, after being cut from what might have been the worst team in organized hockey, he never forgot something his father told him about getting ahead: "It was kind of like his motto—'Saw the wood that's in front of you.' " In the
2013–14 season, Darling enjoyed his most successful
American Hockey League (AHL) season, earning 13 wins in 26 games with the
Milwaukee Admirals.
Chicago Blackhawks On July 1, 2014, the Chicago Blackhawks signed Darling as a free agent to his first NHL contract on a one-year deal. Darling made his NHL debut on October 26, 2014, against the
Ottawa Senators, making 32 saves in the 2–1 win. He became the first former
Southern Professional Hockey League (SPHL) player to play in an NHL game. On November 1, 2014, it was announced Darling had been reassigned to the Blackhawks' AHL affiliate, the
Rockford IceHogs, following starting goaltender
Corey Crawford's recovery from an undisclosed upper-body injury. However, Darling was recalled two weeks later, on November 15, 2014. On February 22, 2015, Darling was promoted from Rockford and placed onto Chicago's NHL roster, replacing
Antti Raanta as the team's backup goaltender, who himself was demoted to Rockford. The Blackhawks also signed Darling to a two-year contract extension. On March 18, 2015, Darling recorded his first NHL
shutout in a Blackhawks' 1–0 victory over the
New York Rangers. On April 15, 2015, Darling recorded his first playoff win after replacing Crawford in net, making 42 saves, with the Blackhawks defeating the
Nashville Predators 4–3 in double overtime. Darling set an NHL record in his debut for the longest relief appearance without allowing a goal (67:44), as well as the most saves in relief without allowing a goal (42). On June 15, 2015, Darling became the first Chicago-area native player to win a
Stanley Cup with the Blackhawks.
Carolina Hurricanes On April 28, 2017, at the conclusion of the Blackhawks season in
2016–17, Darling's rights as a pending free agent were traded to the
Carolina Hurricanes in exchange for the Ottawa Senators' original third-round pick in the
2017 NHL entry draft. On May 6, 2017, Darling agreed to terms with the Hurricanes on a four-year contract. His first season with Carolina was underwhelming, as he recorded a 13–21–7 record with a 3.18
goals against average (GAA). On November 29, 2018, the Hurricanes placed Darling on waivers. At that point, he had a .892 save percentage in seven appearances for the club. He cleared the following day, and joined the Hurricanes' AHL affiliate, the
Charlotte Checkers. On February 10, 2019, Darling was granted a "personal leave of absence" from the Charlotte Checkers and the Hurricanes organization for an undetermined period of time. On June 30, 2019, Darling and a
2020 sixth-round draft pick were traded to
Florida Panthers in exchange for
James Reimer. He was subsequently placed on unconditional waivers for the purpose of buying out the final two years of his contract.
Innsbruck HC Darling signed with
Innsbruck HC of the
Austrian Hockey League in November 2019. He abruptly returned to the United States in March 2020 following the onset of the
coronavirus pandemic in Europe. Darling appeared in 33 contests for Innsbruck, where he posted a 3.34 GAA and .898 save percentage prior to his departure.
Return to North America As a free agent, Darling returned from Austria and agreed to a professional tryout contract to attend the Florida Panthers training camp on January 2, 2021. With the Panthers under the leadership of former Chicago Blackhawks coach
Joel Quenneville, Darling was subsequently released without a contract at the conclusion of camp. On January 26, Darling returned to the roots of his past success in joining the Blackhawks, signing a professional tryout contract (PTO) with the Rockford IceHogs of the AHL, to begin the
2020–21 season. He made a lone appearance in his return to the IceHogs on February 9, allowing five goals on 27 shots. Darling was released from his PTO with the IceHogs on February 17, 2021. He retired from professional hockey after his release. Darling reflected on his career, stating, "I grew up in Chicago, I've been a 'Hawks fan my entire life, I still am a 'Hawks fan. It meant the world to me. My family went to the parade in
2010, I watched
2013 with my mom on her couch and being on the
2015 team and helping them along, oh my God, it makes me emotional just talking about it." ==International play==