U.S. Senator Peter Fitzgerald (R-IL)
Elected 1998
Who the city of Chicago voted overwhelming for in that election: Carol Moseley Braun (D)
Gee, that's funny, when we look at real life, the OPPOSITE occurs from your fantasy world. In the real world:
When the citizens as a whole in a state vote, they are able to elect a DIFFERENT Senator than the one favored by the big cities in their state (if your theory were true, for example, Georgia would elect NOTHING but socialist Democrats to the Senate, since that's who ALWAYS wins in Atlanta and other urban strangleholds)
But when the STATE LEGISLATURE as a whole votes, the big city (Chicago) gets what they want 100% of the time, thanks to them safely controlling most of the seats (including the suburban ones where most of the district is outside city limits) through gerrymandering, and thus getting a veto-proof majority to give the Chicago politicians whatever they want. I have never seen House Speaker Mike Madigan (D-Chicago) ever lose a vote in his rigged body. They rubber stamp WHATEVER he tells them to.
Sorry real life facts don't gel with your fantasy about legislatures representing the "best interests" of the state, and the statewide popular vote only representing the "big cities" As John Adams would say, facts are stubborn things.