Searching for "Prison Break Season 2 Episode 16 subtitles" exists in a gray area. The subtitles themselves are usually user-generated or transcribed, making them legal to download. However, you must own a legitimate copy of the episode (DVD, Blu-ray, or digital purchase from Amazon/Apple TV/Netflix) to use them. Never download video files from pirate sites—support the creators of the show.
Once you have downloaded the Prison.Break.S02E16.Chicago.srt file, here is how to use it: prison break season 2 episode 16 subtitles