In 2013, Jennings recorded a team-leading four interceptions, the second-most in his career, behind 2012's nine interceptions. In the past two seasons, Jennings has recorded 13 interceptions, the second-most in the league behind Richard Sherman's 16. Jennings was an unrestricted free agent for the 2014 season until January 2, 2014, when he was re-signed by the Bears to a 4-year contract. On January 20, 2014, Jennings was named to the Pro Bowl roster to replace Richard Sherman, becoming the second Bears cornerback to make two consecutive Pro Bowls, after Tillman in 2011–12.