Rarely.
When I was a kid, we would MAKE chocolate milk with white milk and Hershey's syrup. My kids make it sometimes with white milk and chocolate-malt flavored ovaltine powder. But my mother NEVER bought premade and I rarely do.
However, I do like Kroger's pre-made chocolate milk. (and otherwise, I'm not a milk drinker). When I was a kid, we used to go to my great-aunt/great-uncle's house for Thanksgiving and they always had Kroger chocolate milk for the kids. It was a Thanksgiving treat. I often buy it for Thanksgiving (but we normally drink it with breakfast, because we have thanksgiving dinner at my in-law's and it's not one of their traditions there.)
Kroger will occasionally run it for $1 for 1/2 gallon and if I see that, I will pick it up "just because," but I haven't seen that sale in a long time (but Kroger is not the store I normally do my weekly shopping at, so I might have missed it.)