Hello how may I help you? Can you tell me from nearest to farthest how far three cities are from Chicago? I can compare these distances. What cities? Jupiter Florida, Maui, and Boston The closest city to Chicago is Boston, MA. Second is Jupiter, FL. And finally, the furthest from Chicago is Maui, HI. Thank you. Which is closer to Chicago Portland, OR or Portland, ME Portland, ME is closer to Chicago. Okay. i thought so. Thank you You're welcome. Is there any other questions you have for me at this time? Nope. You have been very helpful Thanks! I try!