It all depends on how close you want to be to the center. I think you would be okay in either the Magnificent Mile area or North Michigan Avenue - Water Tower. It really isn't that far of a walk from one to the other. The Loop zone is the third best location, but you could end up out of the way depending on which hotel you get. I won the Hyatt Regency in the Loop zone last year on PRICELINE, which is right across the river next to the Mag Mile zone. (Not 100% sure the zone is still the same) As far as which hotel to recommend, really it all comes down to what you want to spend. I am seeing a variety of hotels on HOTWIRE for under $120/night. For example, there is a 3.5* in Mag Mile for $99 with amenities fitness, pool, restaurant, business, and internet, with a tripadvisor rating of 4/5 based on 40+ reviews, which looks to be a match to the Doubletree Hotel Chicago - Mag Mile. I also see a 4* listed at $110/night and a 3* at $115/night for the same zone. The 4* has amenities fitness, restaurant, business, and internet with a tripadvisor rating of 4/5 based on 300+ reviews. This one looks like it could be the Hard Rock Hotel. The 3* for $115 has amenities fitness, business, internet and tripadvisor rating of 3.5/5 based on 240+ reviews. This one looks to be the Inn of Chicago. It really comes down to what you are looking for. Have you thought of going the PRICELINE route? In general, you can usually get a better deal on PRICELINE than on HOTWIRE. But the only difference is that you absolutely have no idea which hotel you are going to get. As for what to do in Chicago. AaronJB might give you a better idea. But definitely check out Navy Pier, Sears (now the Willis?) Tower. Those are obvious. One tip, if you are going to the Hancock Tower, go to the bar on the 96th floor rather than the viewing deck. You don't have to pay an entrance fee for the bar and the view is just as incredible. The money you save on the admission can go towards a drink! Or if you are really cheap, I doubt anyone would notice if you strolled around without getting a drink. Let us know if you have any other questions, either the hotel or the drive (I drove down there for Labour Day last year from Toronto).