I am a chase vacationer from PA. I am only able to take off a max of two consecutive weeks, but I have enough job flexibility to block out a “window” of three weeks, and then I firm things up as the time approaches. If things look good during “week one,” I start my trip on the appropriate day and return two weeks later. If ”week one” looks bad, then I will usually head out for “week two” regardless, and my two-week trip would be “week two” and “week three” of the window I had set. (In some years when even “week two” looked bad I have been able to extend my “window” a bit, but most years I have a hard stop to be back for a certain date, often more so for personal/family reasons than for work).
The three-week window I usually block out is the last two weeks of May and first week of June (specific dates vary based on a typical start being a Saturday). So if you are fortunate enough to be able to take three consecutive weeks off, that’s the period I would recommend. I like the idea of allowing some time into June; I don’t like being “done” by May 31, it just seems too early to me. Having said that, since I usually would end my trip on a Sunday to be back for the traditional work week, it’s slightly calendar dependent, for example if the first Sunday in June is like the 3rd or 4th, that’s good enough for me, I don’t feel the need to go all the way out to the 7th, or to the following weekend which would be the 10th or 11th. If your weeks off don’t have to align with traditional Monday-Friday work weeks and you went strictly by the calendar, then I would do May 15-June 7 or so.
Even if I lived on the Plains, I would like the idea of having at least two full weeks off for those multi-day events that require overnight stays and vast driving distances. It would be nice to live on the Plains and be able to also get those one-off events, whether early or late in the season, or those events that always seem to happen right before or right after my two-week trip. But even living on the Plains, I would enjoy the two week chase vacation just to be fully immersed in nothing but the weather for two weeks, enjoying the surreal cadence of chasing and the nomadic existence of life on the road. Also, it’s hard to imagine many jobs where there is flexibility to take off on short notice for more than just a day or two. Of course, multi-day events don’t seem to happen much anymore, do they? Which I guess eliminates the need for a chase vacation. But as has already been said above, being at home, at worst you end up with some time off and can do other stuff, that would be a lot more productive than some of my recent chase vacations have been.