Crawford was the goaltender for the Wildcats in the 2003–04 QMJHL playoffs, when they ousted the Rimouski Océanic in the semi-finals to advance to the President's Cup final, but lost that series to the Gatineau Olympiques.

Crawford currently holds the Wildcats record for lowest goals against average (GAA) (2.47 in 2004–05), most wins (35 in 2003–04) and is tied with Simon Lajeunesse for most shutouts in a season (six in 2004–05).

[5][6] Crawford also recorded a strong performance against the Detroit Red Wings, stopping 45 of 47 shots in a 3–1 loss on March 11.

[8][9] Crawford was recalled from the (AHL) on November 28 to take the place of Nikolai Khabibulin, who had been injured two nights earlier but didn’t play and served as a backup on the bench.

[11] With starting goaltender Nikolai Khabibulin injured, Crawford made his Stanley Cup playoffs debut on May 24, 2009, in the second period of game four of the Western Conference Finals against the defending Stanley Cup champion Detroit Red Wings, replacing Cristobal Huet.

For the 2010 playoffs, Antti Niemi backstopped the Blackhawks to their first Stanley Cup in 49 years in a six game series win against the Philadelphia Flyers in the finals.

Due to the departures of starter Antti Niemi to the San Jose Sharks and Cristobal Huet to HC Fribourg-Gottéron of the Swiss National League A in the 2010 off-season, Crawford was promoted to back-up goaltender behind Marty Turco, formerly of the Dallas Stars whom the Blackhawks signed in free agency to a one-year deal.

[17] Crawford finished the 2010–11 season, his first full season in the NHL, playing in 57 games with a 33–18–6 record, four shutout wins, 2.30 GAA and .917 save percentage as the defending Stanley Cup champion Blackhawks as a team barely qualified for the 2011 playoffs having finished as the eighth and final seed in the West.

[23] After Crawford entered the 2011–12 season strong, but later struggled as the season went on and was benched multiple times in favour of veteran backup Ray Emery (who signed with the Blackhawks in free agency to fill the void left by Turco’s free agency departure in the 2011 off-season) playing through long stretches of games as a result.

[24][25] However, Emery could not solidify his hold on the starter's role and Crawford reclaimed the team's starting goaltender position.

[28] Entering the lock-out-shortened 2012–13 season, the team re-signed Emery to give him a push for continuing the starting job.

During the 2014 playoffs, Crawford and the Blackhawks would make another deep playoff run as the defending Stanley Cup champions by defeating the fourth-seeded St. Louis Blues in six games in round one and the seventh-seeded Minnesota Wild in the second round in six games before losing in the Western Conference Finals to the sixth-seeded and eventual Stanley Cup champion Los Angeles Kings in seven games, one win short from a second consecutive appearance in the Stanley Cup Finals.

[40] Crawford was named the starter over Darling by head coach Joel Quenneville for the second round against the Minnesota Wild.

On March 17, 2016, The Blackhawks announced that Crawford would miss indefinite amount of time due to an unspecified upper-body injury.

[41] Crawford ultimately returned to action for the season finale on April 9, in a 5–4 overtime loss to the Columbus Blue Jackets.

[47] The Blackhawks won the Central Division and Western Conference, but were swept by the eighth-seeded Nashville Predators in the first round of the 2017 playoffs.

[48] Crawford started the 2017–18 season ranking seventh in the NHL with a 2.29 GAA and fourth with a .930 save percentage in 21 appearances.

On December 1, 2017, the Blackhawks placed Crawford on IR after he sustained a lower-body injury the previous night in a 4–3 overtime loss to the Dallas Stars.

[50] The Blackhawks eventually revealed that Crawford suffered a concussion and would be out indefinitely, but were hopeful that he could return before the end of the season for a playoff push.

[52] After missing 52 games including the first five of the 2018–19 season, Crawford returned to the Blackhawks on October 18, 2018 in a 4–1 loss to the Arizona Coyotes.

Crawford suffered another concussion on December 16 after San Jose Sharks forward Evander Kane shoved teammate Dylan Strome into him, causing him to smack the back of his head on the goal post.

[56] His strongest performance of the season came on March 16, when made a career-high 48 saves en route to a 2–0 win against his hometown team, the Montreal Canadiens.

[58] Crawford missed the Blackhawks' season finale on April 6 against the Nashville Predators after sustaining a groin injury during the team's penultimate game the previous day against the Dallas Stars.

[56] For the first time in his career, Crawford was named the Blackhawks nominee for the Bill Masterton Memorial Trophy, the award given to the player who exemplifies the best qualities of perseverance, sportsmanship and dedication to the game of hockey but didn't make the final three by the NHL.

[61] Crawford started the remaining 10 games of the season before the last three weeks would get cancelled due to the restrictions surrounding the COVID-19 pandemic.

[64] On October 8, 2020, Blackhawks general manager Stan Bowman announced the team would not re-sign Crawford, ending his 17-year tenure with Chicago.

[67] He missed multiple days of the team's subsequent training camp due to "maintenance" or "personal reasons".