I recall my first trip there and it was madness. I flew into Ohare but hotel was closer to Midway and I was telling everyone I was "near the airport." Which airport might have helped ha ha. I avoid downtown areas in most really big cities, because the hotel rooms (though nicer) are also generally much smaller in size with less in room amenities unless you want to spend over 400. Another thing you may want to check into are condos because they rent for about the same as a 4 star hotel room, yet offer 2 bedrooms, 2 baths and a balcony/patio.  
   
 I generally book all my hotel rooms from hotels.com and flights through cheaptickets.com. Sometimes you save with booking them together and other times, not so much. If you're driving, then no brainer... hotels.com will show you all the hotels based on area, amenties, restaurants, etc. Chicago is much like New Orleans when it comes to dining... you really can't go wrong with 90 percent of the well known eateries. Must  try a Chicago dog even if you only take one bite... it's just something you have to cross off your list ha ha.  
   
 I am staying near Ohare as far as hobbying goes, but will be making my way downtown if time and energy permit lol.