Most vpn services will place their data center in chicago since it has much better connectivity in that part of the country. Does it actually have to be in mulwaukee.
I have not seen one that has a data center there but there are many hundreds of vpn services so maybe one does. Many services like netflix or amazon have lists of ip blocks used by vpn and prevent you from using their services from those IP. Not sure about youtube.
You best bet would be to try to find a VPS service in the city. Most larger cities have them...again a lot will be in chicago since it has better internet connectivity. In these you rent part of a server and load your own VPN server on it. These are not blocked as often by the providers. Many...