Chicago is very much an either or city. By that I mean, suitors who live in the suburbs prefer not to drive all the way Downtown. And the ones who prefer to play Downtown won't see you if you're out in the suburbs.
Some companions will do a three or four day tour and stay Downtown for part of their trip and out by O'hare airport for a day or two. When you're Downtown, either The Loop, River North, or Gold Coast are the most popular, centrally located neighborhoods to host.
Another option is to stay around Lincoln Park which isn't exactly equidistant but somewhat easy to get to for people coming from various directions.
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