I doubt it for the 2nd offense . Jail is very expensive for the entities involved so the judges/prosecutors much prefer to send you to to community service and other impediments to your freedom for months to years.
However, your latest would be your 3rd DUI within 10 years. Unless you beat the latest charge, you will be facing significant penalties, including jail time.
Depending on the alternatives, jail time may not be the less-attractive alternative. For example, I currently have a DUI for which I have to pay a fine, 30 hours of alcohol classes, AA attendance, a week of hard manual labor. My lawyer did not informed me of these penalties, but I probably would have opted for jail instead.
Before the peanut gallery jumps in - yes, I am a criminal, and I deserve to be punished. But, given the options of a month in jail, or the classes/work-project/AA regiment, I would actually prefer jail.
Having said all that, taking Xanax is not conducive to driving, and from a purely medical point of view,you should see an addiction specialist.