@Ben Meisel In Chicago, the owner of the building is responsible for the supply water line from the water meter to the building, the city is responsible for the water meter back to the street. Keep in mind, not all meters are placed in buildings! Many are placed in what’s called a meter vault which can be outside of the property, in the yard or sidewalk somewhere. Where exactly is the meter located? This will determine the level of problem you potentially have.
If the meter is in a vault, your cost will be based on a few things. Your yard set up, if it is in the park way, how far back the building sits, and/or (what may be the biggest cost) how much concrete lies between your building and where the meter is. Is tearing up and pouring concrete, or restoring the yard factored in the amount quoted? If so, what is the scope?
Also, if you have a meter vault, and you have to tear up dirt/concrete, you can not do this under the radar. You should be using a licensed plumber who will have to pull permits to get this done, which with time and permit costs, will add about 5-7% to the cost.
I am not sure if insurance will be able to do anything, but worth a call.
CM