If you go with hotels pick nicer ones (4 star or more on Priceline) cheaper and many mid-range places get a lot of heat/attention here...I've been thinking of getting a nice private AirBnB and splitting it with some gals...
Hosting near O'Hare (access to dudes from $uburb$) for a few days and then somewhere near the Loop or Magnificent Mile would be my tip!
Good luck hun!