New York City - 8.34 million Chicago - 2.67 million
New York City - 1st Chicago - 3rd
New York City - One World Trade Center (1,776 ft/541 m) Chicago - Willis Tower (1,450 ft/442 m)
New York City - 1620s Chicago - 1780s
Winters in Chicago are relatively colder. NYC - Summers are warm and humid; winters are cold with a few days of snow. Chicago - Summers are warm and humid; Winters are very cold and snowy.
New York Giants (NFL), New York Yankees (MLB), New York Knicks (NBA), New York Mets (MLB), New York Rangers (NHL), etc.
Chicago Bears (NFL), Chicago Cubs (MLB), Chicago White Sox (MLB), Chicago Bulls (NBA), Chicago Blackhawks (NHL), etc.