Chicago is almost entirely above ground. Very little of the network is below the city.
Out of 224.1 miles of track, only 11.4 are underground (5%).[1] Only two out of the eight lines run that 11.4 miles and the majority of their time is spent on elevated tracks above street level.
That said, a ring around the city would be great. The hub and spoke layout dramatically limits Chicagoans ability to get around.