I guess visiting Chicago might feel more personal but although well equipped for enjoying sports events and culture, Chicago can't match New York for excitement or experience, let alone for variety. You have to see the main sights but also Brooklyn and the boat to Staten Island.
There's so much to photograph, a hop-on and off bus tours you round a lot of the places yo'd want to see. Whatever your interests, New York can satisfy them. Chicago is great and has a good music scene, but can't compete.