Been done before,
From Wiki although there are other sources:
In August 1959, a U.S. Air Force Lockheed F-104 Starfighter performed a low fly-by of the airport during celebration of the opening of a new terminal in Ottawa and accidentally went supersonic over the airport, causing windows and parts of the walls of the new terminal to shatter. The terminal was only reopened in 1960.
Construction of the airport terminal building began in 1957. As the project neared completion, a military demonstration proved disastrous; a U.S. Airforce F104 Starfighter broke the sound barrier and virtually every window in the structure. There was also significant structural damage inflicted on the building. This mishap added approximately one year to the construction schedule, and $300,000 to the budget of $5 million. The terminal was finally opened by Prime Minister John Diefenbaker on June 30th, 1960.
The damage was fairly substantial, quite a few red faces around.