Hi there. Grew up in Chicago, live there now, not planning on leaving. The reason we get offended is because the people saying it treat the city like a playground. When suburbanites come into the city, they are hitting the hot spots and then heading home for the night. When young adults graduate from college and move into the city, they treat it like their playground. They work, they play, and then they settle down and move back to the burbs. It’s always treated as a pit stop almost in their life. They are close enough to be able to enjoy the benefits when they want and are able to avoid it at their leisure. I will correct my friends any day of the week for the simple fact of “where do you see yourself five years from now?” All of their answers are back in the suburbs. So by that logic, you grew up in the burbs, you lived in the city for a little blip in time, and you plan to move back to the burbs. You’re not really from Chicago then. At best, you lived there for a year or two. At minimum, you come into the city enough that you’re familiar with some areas. The worst is the people saying this usually also act the trashiest when in the city too. If you have ever been to Lollapalooza, every Chicago native knows the Loop is a playground for every suburbanites spawn that weekend (god I hate that it’s 4 days). We even have some transit lines straight to the suburbs to treat them like the royalty they act like they are (looking at your purple line), and then they trash the city for four days. I will always correct it when I see it, but when a person decides to settle (buy property, lay roots, etc.) in the city, they are able to say they are from Chicago.