Although not a true windowed mode, the game can be run to give the impression. If the desktop resolution is greater than the game, the game will be centered in on the desktop at 640x480.
Here is how to toggle it should it become unusable:
Alternatively, you can go to SIMTUNES.INI (located in C:\Windows) and change UseDirectDraw to TRUE.
Although the game installer is 16-bit, the actual game is 32-bit. The only way to play it is to use an alternate installer:
Open the file SIMTUNES.INI (located in C:\Windows) and change UseDirectDraw to TRUE.