I think observing your plant is a good idea, they can teach us if we pay attention to them....
In my experience Hardy Chicago will take at least 80 days to ripen a fig from when it is visible, depending on factors such as heat, sun, age of plant, moisture levels in soil, crop load,phase of moon, etc. ln northern areas, season length is as big an obstacle as cold hardiness for ripening the crop. Simply enough to do the math working from first frost date in your area. For me, I am a past the cutoff point- time to get ruthless.
My 2 year inground Marsailles Black VS has set a respectable crop,
2nd year St Rita has a few too.
Many of mine are in pots that come inside for the winter, looking forward to some breba crop figs from this second leaf plant. These had the advantage of an early start in my hoophouse over my inground plants which broke dormancy a month or so later.