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fortunately or unfortunately depends who you ask my XJ is not the primary vehicle. My question is how often do you start the car? When there is no snow on the ground I try to drive it around once every week. How about you guy/gals?
What are your concerns?
1. Battery - get a CTEK battery maintainer.
2. Fuel - use STA-BIL fuel stabilizer
3. Tires - increase pressure to 45 lbs.
4. Engine lubrication - I wouldn't start it unless it ran for several minutes after reaching normal operating temperature. You're in Chicago and winter will be over soon.
My wife doesn't drive and we own three late model vehicles, of which the XJL is the oldest. I drive them interchangeably, depending on where I'm going and what I'm doing. The Jaguar seldom sits neglected for more than three days at a time, nor do the others although the 2015 Mustang convertible is driven a bit less this time of year but more frequently in summer, and vice-versa for the 4WD 2017 Lincoln Navigator. Stuart pretty much nailed it with his list of concerns and remedies above.
I've got collector cars and more cars than I need and unfortunately not enough time as I am not retired. I try to drive each about once every month to two months at the longest. I once went six months after a back surgery and had some serious flat-spotting of tires, but that was the only ill effect.
I can't say how long you can go before bad things happen, but it will have more to do with where and how the car is stored than anything, and maybe a little to do with the engineering of the car itself, the materials and quality, etc. If its just parked outside, things will deteriorate and corrode a lot quicker than if its parked inside a nice, dark, insulated garage. But Stuart and Mikey give great advice for cars that will be parked for an extended period.