Usually the ladies that visit here in Chicago Split their time into 3 different areas.Nw suburbs(Schaumburg),ohare and downtown.IMO all 3 areas are nice

River North for sure, no disrespect to the sprawling mega mega malls chain food restaurants deep deep suburbia and have a love for driving and Starbucks and driving to Starbucks and then you know the mall and IKEA.  It's great if you love the suburban family thing.  
As far as work or touring, I've only worked in the city and it works well for me. There are ladies with suburban location and I assume that works well for them.  
I'm in River North daily, so obviously it is my preference you'll never be bored and business is solid.

Each has its good points and bad Still in Schaumburg Us guys in the burbs can see still in the city and the city guys can see you spend time in both places

River north is the best neighborhood and also has the best selection of restaurants and activities for when you are not working.