Being born and raised in Honolulu, I know where the locals go and the tourists go.
Honolulu, on the island of O'ahu, is the biggest city of all the Hawaiian islands. You can find the iconic Waikiki Beach along with the pretty pink Royal Hawaiian hotel. My absolute favorite beach to go to is also downtown.
Although Chicago is the third largest state in the United States, it's neighborhoods make it feel much smaller than it actually is. Although the weather here goes to extreme, the people are quite nice with their Midwestern charm.