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On March 13, 2019, Sitton was released by the Dolphins.

On April 4, 2019, Sitton announced his retirement from the NFL after 11 seasons. On December 4, 2019 Sitton announced he would retire with the Packers.

In 2017, Sitton started 13 games at right and left guard for the Bears. On February 20, 2018, the Bears declined an option on Sitton's contract, making him a free agent.

On March 16, 2018, Sitton signed a two-year contract with the Miami Dolphins.

On September 14, 2018, Sitton was placed on season-ending injured reserve after suffering a torn rotator cuff.

In March 2017, Sitton revealed that he felt like he was hitting a milestone achievement entering his 10th NFL season. "I have been lucky. A lot of guys are not lucky. They get the injury bug and things like that. I have been blessed to avoid that. And really, that is the difference maker in this business is being able to stay healthy. and I have been able," Sitton said.

On September 3, 2016, Sitton was released by the Green Bay Packers, in an unexpected move.

On September 4, 2016, Sitton signed a three-year contract with the Chicago Bears worth $21.75 million with $10 million guaranteed.

Sitton and his wife have been married since July 2016. They were married in Pensacola. In late July 2017, the couple's first daughter was born. In April of 2019, the couple's first son was born.

Since 2013, Sitton has returned to his high school to host the Josh Sitton Football ProCamp for youth in the area. He is also on the board of the Studer Community Institute. His main focus with the institute is kindergarten readiness. Sitton hosts the “Light Up Learning” event annually in an effort to help this cause. Since retirement he has been more involved with his construction company, Bear General Contractors, which specializes in commercial construction in northwest Florida. Sitton recently donated to his alma mater, Pensacola Catholic High School, as part of a campaign to add onto the athletic facilities and a new cafeteria.

Following the 2012 season, Sitton was moved to left guard. He had spent the first five years of his career at right guard.

On September 2, 2011, the Packers signed Sitton to a five-year contract extension. On January 21, 2013, Sitton was chosen to replace Mike Iupati in the Pro Bowl, his first selection. On January 3, 2016, Sitton started his first career game at left tackle in place of the injured David Bakhtiari as the Packers played the Minnesota Vikings in the regular season finale that decided the NFC North champion.

At the end of the 2010 season, Sitton and the Packers appeared in Super Bowl XLV. He was a starter in the 31–25 victory over the Pittsburgh Steelers.

Sitton was drafted by the Green Bay Packers in the 4th round of the 2008 NFL Draft. In 2010, he was named Offensive Lineman of the Year by the NFL Alumni Association and was selected as a Pro Bowl alternate. Sitton was a key part of the Packers offensive line. Sitton started every game at right guard during the 2009 and 2010 seasons, including all the team's playoff games.

In his true freshman season at UCF, Sitton played in all 11 games with four starts at right guard. He was moved to right tackle for his sophomore season, where he started all 13 games for the Knights. He remained a starter at right tackle for the rest of his college career, blocking the way for Kevin Smith, as he rushed for 2,567 yards in 2007, just 62 yards short of breaking Barry Sanders's NCAA single-season rushing record (2,628) set in 1988.

Regarded as only a two-star recruit by both Rivals.com and Scout.com, Sitton was not listed among the best offensive lineman prospects in the class of 2004. He chose UCF over offers from Nicholls State University and the University of Alabama at Birmingham.

Josh James Sitton (/ˈ s ɪ t ən / SIT -ən; born June 16, 1986) is a former American football guard. He played college football at the University of Central Florida and was drafted by the Green Bay Packers in the fourth round of the 2008 NFL Draft. He has made four Pro Bowls and won Super Bowl XLV with the Packers, and also played two seasons with the Chicago Bears and one season with the Miami Dolphins. After 11 seasons in the NFL, Sitton announced his retirement on April 4, 2019. He officially retired with the Packers on December 4, 2019.