I had this game when I was a Kid, it was pretty cool I thought, you played as the captain of a crew of cadets doing Holodeck missions, it was also kind of a "choose your own story" game where FMV videos played and your decisions affected the story. The best part was the appearances from Shatner and company it was great to see them again and they actually put some effort into their performances.
The game came on 6 discs and included a novelisation of the game which was a fun read.
In fact, it's 5 discs, plus 1 expansion "Chekov's Lost Missions" which must be purchased separately.
The movie clips and music are really nice, but poor control makes it difficult to play on PC.
I remember seeing Chekovs Lost Missions on vacation and pleading with my parents to get it for me (i was like 9 or 10 at the time) but they wouldnt, i never saw it again, might ebay it just to see what it was all about