Yupyup, it'll get you in trouble. They can't press charges, of course, but they'll most definitely rebuke you, though the severity of the punishment depends on your school's internet policy, which can change from year to year.
For instance, a few years ago my school's internet policy was far less stringent, for not very many people tried to bypass the school's flimsy filter. But when me and a few of my nerdy friends came along and began using proxies and other methods of circumvention, they began patching up all the glaring holes it had in its system, and slowly but surely, using the internet from school became a restricted, monitored, and limited experience. Today, my school uses a monstrous, privacy-invading opus for a filter, complete with the ability to track which websites each individual student has accessed (and yes, clearing your History folder doesn't work
), a keylogger that tracks each and every key a student presses, and an ever-expanding blacklist of websites. And they are one-hundred percent able to do it, because of the Terms Of Use agreement they make the student body sign if they wish to have computer privileges. How's
that for interwebs?
Moral of the story: Sure, you can do it. But be wary of the consequences that could result from being a thorn in the school's side, both short- and long-term.