2016 Chicgao Bears Pro Bowlers: Josh Sitton, Jordan Howard
The Chicago Bears did not have a single member of the 2017 roster make the Pro Bowl That is why the 2018 turnaround from Matt Nagy was so impressive. In 2016, it was a John Fox team with a lot of different characters. Josh Sitton made the Pro Bowl, mainly based on name value. He made the All-Pro with Green Bay the two years prior and had a good enough year.
Jordan Howard had an excellent rookie season, with 1,313 yards and six touchdowns. You could argue that if anyone should have made the 2017 Pro Bowl, it was Howard, who had 1,122 yards and nine touchdowns the year after.
2015 Chicgao Bears Pro Bowlers: Kyle Long
Kyle Long made his first of two Pro Bowls in 2015. The 2013 through 2015 season was Long at his best before the injuries caught up to him. Still, he was able to get in half of a season on the 2018 team before the 2019 team ended his career.
2014 Chicgao Bears Pro Bowlers: Kyle Long, Martellus Bennett
The only time Martellus Bennett made the Pro Bowl was in 2014. It is funny that the memory from a team with Jay Cutler, Alshon Jeffrey, Matt Forte, and Brandon Marshall is that Bennett was the only skill player from that team to make the Pro Bowl. This year was the end of the Marc Trestman era.