Hello how may I help you? Hi. I was hoping you could help me with something today. Sure, what can I help you with? Could I know what city is closest to Chicago then list the second and so on for St. Louis, Amarillo, Los Angeles. Sure the closest city to Chicago is St Louis, followed by Amarillo, then Los Angeles. Wow. I guessed without even knowing. I suppose I just wanted confirmation. I am hoping to travel this summer. I wanted to plan my route. Ah okay, would you like to know anything else? Sure. I am trying to see what cities are further away heading eastward. Pittsburg, Cleveland, and Boston. Closest to Chicago is Pittsburg, then Cleveland, then Boston, going eastwards. Great. I am excite to plan these trips. Awesome, hope you have fun!