Would the large buildings breakup the 200+mph winds or would the warmer air over large cities help dissipate it?
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No, an EF4 would devastate the city.
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More than likely it would not bring down a skyscraper but would destroy smaller buildings less than 5 stories because they don't have the same structural requirements. I don't think the warmer air would have that much of an effect. An F4 tornado has wind speeds of 207–260 mph, not 450 knots.
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It wil destroy chicago..
F4 tornado has 450 knots speed
F4 tornado has 450 knots speed