Answer: 4,210 kilometres (2,616 miles) taking this route:
Take HIGHWAY 401 - WEST, from Toronto, to the BRIDGE TO U.S.A., at the DETROIT-WINDSOR BORDER X-ING. You will be crossing into Detroit, MICHIGAN, U.S.A. via the AMBASSADOR BRIDGE. Once you are in Detroit, MI, you are going to follow signs to I-94 WEST to CHICAGO.
Take I-94 WEST across to I-294 (TOLLWAY) - NORTH to WISCONSIN, in Chicagoland, ILLINOIS.
Take I-294 NORTH, on the TOLLWAY, to I-90 (TOLLWAY) - WEST to ROCKFORD.