I've lived in both cities, seven years in Seattle and now 14 years in Chicago (married to an Asian woman), after stints in Berlin, Nürnberg, Philly and NYC. I don't think the answer is quite that simple. Some cities make you feel at home, some don't. That's different for every person. Seattle is nothing like Tokyo - much more like a regional city in Japan in terms of size and feel. In Seattle, my perception was that the expatriate and "Third culture kids" community was very small, whereas in Chicago it feels much larger. I don't know much about Tanaka the person, so I can't say where his preferences lie. I would love for Tanaka to land in Seattle, since my sports loyalties are to the Mariners and Huskies, but I wouldn't put too much weight on the differences between Chicago and Seattle without knowing much more about Tanaka the person.