O'hare all the way! I have sentimental reasons for feeling this way. When I was very young I was taken out to the building site when ORD
was just a darkened, glassless hulk. The original terminals were built but it was still a few months away from opening. It has grown into one of the world's great airports. For all its hugeness it is very efficient and pleasant to be in. The international terminal is the best in America, in my opinion, and in spite of the surfeit of McDonald's there is still a very good restaurant, it used to be called the Tartan Tray, now it is a "fancy" restaurant in the old TWA terminal, now American, where the views of the runways and terminals is spectacular.
Midway is much-improved and much-needed but it's an also-ran in the modern annals of Chicago aviation. In the old days it was exciting with all the Boeing 337s and Connies, now it's just a bus terminal for the LCCs. Watch the Hitchcock film 'North by Northwest' for great tarmac shots at night!
Meigs never met its potential, only Ozark flew a few FH7s into it at one time, now it is destined to become the Richard Daley jnr Memorial casino and dumping pier. Meigs COULD have been like London's City Airport had the city managers suppressed their personal financial interests and opted to act in the public's best interests instead. So goes Chicagi politics.