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I would he happy to help assist you in understanding your dream.
Usually people and places in dreams are symbolic. in this case they are as you mentioned the present facts in your and his life.
The woman in the dream can be symbolic of a new relationship coming into his life. This relationship can be with anything in his work life, and or personal life. Going to Chicago can be showing a new direction he is taking in life. It most likely pertains to this woman. Something new in his life has caught his attention. I hope this helps, feel free to ask any questions.