It is probably best to think of Chicago as two separate markets.  Suburban (mostly Schaumburg/Rosemont/Oakbrook) and downtown.  The suburbanites don't want to come downtown due to parking and traffic while many city dwellers have no easy way to get to the suburbs.  I think the best strategy is to split your stay into two parts.

o'hare if you want to stick to one location. It can be access by guys downtown and suburbs.

but we guys can be lazy so splitting between dt and burbs will be good

Oakbrook, Downers Grove, Lombard area is the best area for the suburbs followed by Schaumburg area.  Many guys avoid Ohare believe it or not because you always have to pay to park but on the up side, it opens up access to the City guys as well as the North Shore.  

Downtown is a great place if you want to shop but don't stay down there too long to work or you might be disappointed.  

Good Luck

Mike

Thank you guys for all the info. I have a lot to take into consideration......

I don't think you are coming to shop. I say split time between downtown and the burbs, Oakbrook and Schaumburg has been mentioned. Stay five days (T-Sa), allowing a half-day for travel to the other location. That gives you two full days in each locale. Like many have stated, O'hare can be a double-edged sword, but is workable so long as you avoid the hotels with poor parking or carded elevator access.