Chicago has a wealth of great areas. There is downtown/Gold Coast. Lots to see and do there, plus great eating establishments.

Then you have the West burbs, Oakbrook/Lombard area. Usually less expensive but still very nice hotels. Also has some great places to eat and two large malls nearby.

Lastly there is the Northwest burbs, Schaumburg and Arlington Heights. Also less expensive hotels than downtown and it has Woodfield Mall, a great place for shopping.

Those seem to be the most popular with visiting gals. The downtown guys usually don't like going out to the burbs and the suburban guys don't like the hassle of downtown traffic and parking issues. Many smart ladies split their time between downtown and one of the suburban areas mentioned above. Good luck in whatever decision you make.