Holgabean,
Welcome to the forum. I used to live in Chicago, so I do know quite a bit about it. I spent
an incredible weekend at the Drake one time when I needed to a quick getaway, but it is definitely in the middle of downtown and it is decidedly expensive now. It is probably not what you are looking for. Have you been there before? How much is your budget on this trip [how much do you want to spend for your hotel per night]? In terms of your taste, do you like the classics or the modern? It will be harder getting a hotel or motel room out of the downtown area without having a long drive or bus or train ride. The northside is magnificent as is the Southside, but you would expect a thirty minute commute at least to get to where most of the galleries are.
I know they may not be in your budget, but two of my favorite hotel properties in Chicago right now are:
The Sofitel that is located near the Water Tower and Lake Michigan that has rooms starting at just over $200.00 per night, which is not bad for a state of the art modern hotel in a convenient and scenic location.
On the more
affordable side of things, there is The Windy City Inn that is more of a bed and breakfast inn with rooms starting at $115.00 per night. It is located in Lincoln Park on the near northside. It would be a short bus ride downtown from there. [about 3 miles]
FT
The photo above is from Wikipedia Germany that was uploaded by Magnus Manske.