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.
On January 20, 2014, Jennings was chosen for the Pro Bowl to replace Richard Sherman and joined a list of Bears cornerbacks who had made two consecutive Pro Bowls since Tillman's performances in 2011-2012.