Way back in my Win95/98 days I had a game titled TRACON which was much like the one I just found, but TRACON would not run in WinXP.
I accidentally ran into ATCSimulator 2
This game runs almost exactly like TRACON.
What these games do is allow you to choose a TRACON area, like the Chicago O'Hare (ORD) TRACON area. (see URL link, game screenshot below)
(click for larger view)
(Did you notice how similar the game screenshot is to the pictures in the URL page?)
Then you act as an ATC Controller and guide aircraft on takeoffs, landings, flying through the area, etc. This includes sending voice commands (via a voice simulator after typing in text commands) to change speed/altitude/heading and hearing the pilots reply.
Of course you have to observe all the rules on aircraft separation, airport landing speeds & runway headings, and specified routs.
I spend hours with the old game and I'll likely spend hours with this updated version.