Born Frank Milano in Massapequa, New York, "Sonny" trained with the USA Hockey National Team Development Program from 2012-14 and was a highly rated prospect heading into the 2014 NHL Draft.

The Blue Jackets selected him in the first round (No. 16) of the 2014 draft, and Milano signed a three-year entry level contract on Sept. 11, 2014, forgoing a commitment to Boston College.

After spending most of the 2015-16 season with Lake Erie, the Blue Jackets' American Hockey League affiliate, Milano made his NHL debut against the New York Islanders on March 31, scoring his first NHL point, an assist, in his next game against the Carolina Hurricanes. He returned to the AHL and had eight points (four goals, four assists) in 17 games to help Lake Erie win the Calder Cup.

Milano played most of the 2016-17 season with Cleveland; he got a four-game call-up with the Blue Jackets but was scoreless. He also appeared in one Stanley Cup Playoff game.

It wasn't until the 2017-18 season that Milano scored his first NHL goal (Oct. 6 against the Islanders). He finished with 22 points (14 goals, eight assists) in 55 games.