Were there ever any plans to demolish the Chicago "L"TM system and replace it with subways, as has been done in New York and Boston?

A; Yes! There have been several. But, none have ever proposed abandoning the "L"TM completely, just replacing it with subways in the business district. The first transit plan that included the removal of the Loop was the Plan for a Unified Transportation System for the City of Chicago in 1927. The plan called for several new subways, including a Michigan Avenue Subway, a State Street Subway, a Halsted Street Subway, and a Clark Street Subway. It also included a new Loop Subway under Lake, Wells, Van Buren and Wabash to replace the elevated, plus extensions out Lake (with a branch up Milwaukee) and Van Buren (with a branch down Blue Island). It was proposed again in the Local Transportation Plan for the City of Chicago in 1937. Again proposed was the State Street Subway (on which construction started the following year). Also proposed was a Van Buren-Dearborn-Lake Subway (with a branch up Milwaukee), a Wells Street Subway (connecting to the "L"TM at Hubbard/Franklin), and a Clinton ...  more