Pieces from the Here & Now edition of Monopoly once flew on a space shuttle mission. (source) Chess has gone up on several missions, and the astronauts have played against the ground on a few of these missions.

A shuttle mission doesn’t go up until the captain loses at a game of poker.  (source)

Which is the only Monopoly edition to feature a space shuttle piece? Answer.

Boym once made a Chess set (limited to 8 copies) with a space shuttle as one of the pieces. The Space Store has a space shuttle themed set you can buy for $30. There have been a few space shuttle themed board games (on BGG).