I don't remember so clearly, but in my impressions there were many Canadian flags neither in New York nor in Chicago. New York seemed to have more nicely exhibited French, British, and Italian Flags along side of American flag on their streets. It's nothing like in Toronto where there are American flags all over the city.
When I visited New York City many years ago, I remember seeing a huge Canadian Flag almost torn off (the red part of the flag almost cut out and dangling) in front of a high-rise building... it was as if the flag was cut by a knife intentionally.