Low clouds hover below some of the amzingly tall buildings that make up Chicago's fantastic skyline. The Hancock Tower with it's two spires clearly above the cloudline stands out as one of the city's more prominent symbols.
When arriving in Montreal by air you might get lucky with your approach to Trudeau Airport and fly right past the downtown core. From that perspective you can view Mont Royal, downtown itself, Old Montreal and the port.
Downtwon Chicago is an amazing array of water, steel and glass... beautiful buildings set in a functional pleasing manner for the everyday pedestrian.