2015

On May 2, 2015, Chickillo was drafted by the Pittsburgh Steelers in the sixth round (212th overall) of the 2015 NFL draft.^[8] Chickillo was the 24th defensive end drafted in 2015.^[9] On May 11, 2015, the Steelers signed Chickillo to a four-year, $2.37 million contract that includes a signing bonus of $73,700.^[10][11]

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Steelers draft Anthony Chickillo 212th overall

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On September 6, 2015, he was waived by the Steelers after initially making the 53-man roster. He was signed to the practice squad three days later. On September 30, 2015, Chickillo was activated from the practice squad to the Steelers' active roster.^[12]

On October 18, 2015, he appeared in his first career game against the Arizona Cardinals. He appeared in seven regular-season games for the Steelers in his rookie year, recording six tackles and forcing a fumble. The following week, he recorded his first tackle during a 23–13 loss to the Kansas City Chiefs. He had a season-high two tackles and forced a fumble during the Steelers' Week 17 victory over the Cleveland Browns. Chickillo finished his rookie season with a total of six combined tackles and a forced fumble, while appearing in seven regular-season contests and two postseason games.^[13]

2016

He began his second season as the third left outside linebacker on the depth chart behind Bud Dupree and Arthur Moats.^[14] Although he was mainly featured on special teams, he began to receive more reps as a rotational outside linebacker after Dupree missed the first ten games due to an abdominal injury.

On October 9, 2016, Chickillo recorded three solo tackles, a forced fumble, and his first career sack on New York Jets' quarterback Ryan Fitzpatrick, during the Steelers' 31–13 victory. The following week, he earned his first career start against the Miami Dolphins and finished the loss with three solo tackles. During a Week 9 13–21 loss to the Baltimore Ravens, Chickillo made a season-high six combined tackles and was credited with a half a sack on Joe Flacco. The next game, he made a total of four tackles, forced a fumble, and sacked Dak Prescott during a 30–35 loss to the Dallas Cowboys.^[13]

2017

On February 14, 2017, the Steelers signed Chickillo to a one-year, $615,000 restricted free agent tender.^[10][15] He returned as the Steelers' third left outside linebacker behind Dupree and Moats, but began the regular season featured on special teams.

On September 10, in the season-opening 21–18 victory over the Cleveland Browns, Chickillo had two sacks. In addition, Tyler Matakevich blocked a punt, which Chickillo recovered in the end zone for his first career touchdown and gave the Steelers their first points of the season.^[16]

2018

On March 13, 2018, the Steelers extended an original round tender offer to Chickillo as a restricted free agent. On April 21, 2018, Chickillo officially signed his one-year, $1.90 million contract.^[10][17]

2019

On March 12, 2019, Chickillo signed a two-year, $8 million contract extension with the Steelers.^[18] After he was arrested for domestic violence on October 20, 2019,^[19] he was placed on the exempt/commissioner's permission list on October 23, 2019.^[20] The domestic violence charges were withdrawn on October 30, and he was brought back to the active roster on October 31.^[21] On March 16, 2020, Chickillo was released.^[22]