Ok I will be traveling to Chicago from 11/8/12-11/14/12. I will be staying in Merrillville for my buddy's wedding from the 8th till the 11th then taking the train to downtown. I have never been to Chicago and it is my and my girlfriend. We are 26 and will be doing a lot of exploring (food, clubing, and landmarks). I am a little confused on what the "express deals" are and how to do this bidding. In Merrillville we are looking at the Best Western (cheapest with free breakfast). I need help with trying to find a place in the areas: (11/11/12-11/14/12) Lincoln Park Millennium Park, Loop & Grant Park Area North Michigan Ave - River North Area We are budgeting around $125 a night but would like to spend under $100 if possible. I was told the rates go down in the winter? Also at what point is the contract binding/ when will I know what hotel I got? I read about the difference using priceline and hotwire. We are not set on a particular hotel but will spend more to get a nice place. Thanks in advance for the help!!