How to Get Daughter to Drink Milk from a Cup?

Dear Laura,
Since she drinks water and juice from a cup, I think it's a matter of her associating milk with her bottle and it's the bottle she doesn't want to give up.
Sometimes it takes a couple of days when you are breaking them from the bottle, but if you give in and give the bottle to her, it just sets you back at square one.
She'll drink milk from a cup when she gets it figured out there will be no more bottles. Teach her to drink from a straw. That might be a new novelty for her and maybe she'll drink her milk that way. Just keep trying.

Just get rid of all of the bottles. She will be fine for a few days without drinking milk since she gets her dairy in other ways..

Maybe take her to the store and tell her all the bottles are broken so she needs to pick out a special "Milk Cup".

My daughter had a hard time just trying to use the cup. I don't know how you are offering it too her. But when you sit down for meal just put it in front of her. Don't give it to her or put it in her mouth, let her be the one to decide to drink out of it. Once she takes a few sips make sure you praise her for doing a good job. Maybe she needs to make the decision for herself instead of being forced to drink out of it. You might have to hang onto the bottle until she does it but if she does it on her own it will be better for everyone. I also agree to take her to pick out her own cup.

It doesn't matter if milk comes from a bottle or a cup. What causes milk tooth rot in children is them holding their bottle in their mouth all night with the milk dripping on to the teeth. The saliva can't wash it away if it is constantly being replaced with fresh milk. If you are not giving her the bottle and letting her hold it in her mouth all night then it is okay. My Pediatric Dentist says so and it is just common sense once I thought about what he said. I drink milk, the kids drink milk, all day and we don't run brush our teeth after and our teeth don't rot from it. She should be getting 16-24 oz. of milk a day. Cutting out the bottle is okay, of course, and many moms do it fine.

It sounds like to me that she still has that need to suck and it needs to be met. Otherwise thumb sucking or sucking some other thing can happen.

Does anyone in your house drink tea or coffee? And if so, does she show any interest in that? We have a child who loves to 'help' his grandpa make the coffee in the morning, and have found that he loves sitting at the table and drinking his "milk coffee" while grandpa drinks his cup of regular coffee. I don't mean that we give him coffee diluted with a lot of milk... but that we put his milk into a coffee mug and he sits and drinks it that way.
You might also try putting a little bit of chocolate syrup in her milk to make it different than the milk she's accustomed to drinking. I know at her age we tend to avoid much chocolate in the diet, but a little bit in the milk won't hurt her if it helps her make the transition to drinking milk from a cup.

I didn't read all the way..but this is how I progressed my girls...

bottle, then sippy cup, then straws, then justs a regular cup.

Have you tried the nuby sippy cups? It is almost a cross between bottle and sippy because the spout is so soft, maybe she would use that as a transition to get away from the bottle. My DD once took one when I ran out of liners for her bottle and didn't have anything else to give her her milk in at a friend's house.