After three professional seasons, Oesterle played his first full NHL season in 2017-18. The native of Dearborn Heights, Michigan, opted to stay in-state after not being selected in the NHL Draft and played three seasons at Western Michigan University.

As a freshman in 2011-12, Oesterle helped WMU win the Central Collegiate Hockey Association championship. In 2013-14, he had 17 points (two goals, 15 assists) in 34 games, then signed a two-year, entry-level contract with the Edmonton Oilers on March 31, 2014.

Oesterle finished 2013-14 with Oklahoma City of the American Hockey League. He started 2014-15 in the AHL and was called up by the Oilers and made his NHL debut against the Anaheim Ducks on Feb. 21, 2015. He got his first NHL point in his third game, earning an assist against the Los Angeles Kings on March 3, 2015.

After playing 25 games in three seasons with the Oilers, Oesterle signed a two-year contract with the Chicago Blackhawks on July 1, 2017 and showed enough to become a full-time NHL player. He scored his first NHL goal against the Oilers on Dec. 29, 2017.

The following season, Oesterle had NHL career highs of six goals, 14 assists and 20 points in 71 games. He was traded by the Blackhawks to the Arizona Coyotes on July 12, 2018.