Does chocolate milk have caffeine in it?

Yes: Chocolate is a blend of hundreds of chemicals with no set formula. It includes the close chemical cousins theobromine and caffeine, as well as others. Once a company blends it with other agents to make a commercial product it will have some consistency in makeup. Theobromine and caffeine have similar effects on the nervous system and digestive tract.

No, but cocoa, : which is the base of chocolate contains Theobromine, which is a stimulant. Caffeine is metabolized in the body quickly to theobromine, theophylline and parazanthine. People are more familiar with the term caffeine, hence the statement that chocolate has caffeine. Concentration depends on dark chocolate, pure cocoa and milk chocolate.

Yes, but not much.: The long answer: caffeine and theobromine are naturally occuring in the plant from which chocolate is made, Theobroma cacao, however there is no added caffeine in most chocolate milk or ice cream. Energy drinks are an exception. The amount is very low, but there are other health concerns about chocolate milk such as sweeteners: https://www.caffeineinformer.com/caffeine-content/chocolate-milk

Yes: "An average 8 oz. glass of chocolate milk (250 ml) has 2 to 7 mg of caffeine." REF: http://www.caffeine-content.com/caffeine-in-chocolate/caffeine-in-chocolate-milk/ Cocoa beans contain caffeiene.