Olesz, 27, has one-year left on his six-year, $18.75 million contract that comes with a salary cap hit of $3.125 million.
However, Olesz is set to earn $4.25 million next season.
Montador, 33, has two-years left on his contract that comes with a cap hit of $2.75 million.
He is set to earn $2.3 million next season and $1.8 million in 2014-15.
Bolland, who scored the Cup clinching goal for the Blackhawks, has been the subject of trade rumors for some time. The Hawks are looking to obtain a new second-line center this off-season and need the space, both on the roster and financially, to afford an upgrade at that position.
In 35 games with the Hawks this past season, Bolland registered seven goals and seven assists for 14 points.