This is lovely. It is also very "Chicago" looking, which is great.
The grass under the table would be difficult to maintain. I think pavers would be a more practical option.
I believe that constructing the (stone?) awning would be a major endeavor since it would need to be supported from within the structure(?) I would prefer the support happen on the exterior. Because of that and all the brickwork, I believe this would be quite expensive and difficult to construct.