Legal Question in Traffic Law in Maryland

Depends on which judge and prosecutor you have, but generally it's unlikely. You should definitely get an attorney though because even without jail this is a 5 point ticket which is equivalent to a major speeding ticket and will dramatically increase your insurance rates. It would be more cost effective to get a lawyer to get it dismissed.

In Baltimore County, the chances of going to jail for driving without insurance are slim on a first offense and good driving record. However, with the points for a conviction of this offense will make your future insurance premiums sky high. Talk to a lawyer about defenses and other means to keep points off your record. The attorney cost will probably be less than your next 3 years of increased insurance premiums.

While no one can give chances per se, because ultimately that depends on the impression that your individual case creates in the prosecutor and the judge, you can improve your chances by resolving the insurance issue and any other issues pertaining to your license and outstanding tickets before going to court.