Well, there are a few ways you could go about this. First of all, if proximity to McCormick Place is your number one priority, then you shouldn't be targeting the Loop zone. The Hyatt Regency McCormick Place is actually connected to McCormick Place via enclosed walkways, and that hotel is located in Hotwire's "South and West of Loop" zone and is rated 4* according to their vacation package listings. I'm not aware of any other hotels in that zone that could conceivably be considered 4*, so as long as you stick to that star level, you don't have much of a risk of ending up somewhere in the western part of the zone, away from McCormick Place. Of course there are never any guarantees with Hotwire or Priceline. :) However, if you want to try to target the Hyatt Regency McCormick Place, I would actually recommend that you try bidding on Priceline. Priceline has a Chicago zone called "Greater Chicago," and similarly to Hotwire, the Hyatt is the only 4* hotel known to be located in this zone. Usually hotels will go for a bit cheaper on Priceline than they will on Hotwire, that's why I say if you want to target this property I would try Priceline first. Conventional rates for the Hyatt are very high for your dates, but Hotwire shows the 4* that I would strongly assume is the Hyatt for $92/night, so you'd probably be able to get it on Priceline for a bit cheaper than that. The downside to staying in that area/zone is that apart from McCormick Place itself, it doesn't have much to offer. Especially at night, the area would be dead and not pleasant to walk around in. To get to anywhere you might want to visit or eat, you'd probably have to take a fairly long cab ride. If having to commute to McCormick Place every day wouldn't be an issue for you, then I would refer to my previous comments on the Loop, NMA, and Mag. Mile-Wacker Dr. zones and recommend that you stay in whichever one sounds best to you or whichever one you could get cheapest, depending on your priorities. If you haven't discovered them already, there are lists of all the hotels that users have won in various Chicago zones on Hotwire and Priceline HERE. They may help you decide which zone would be best for you, and if you decide to use Hotwire the list may help you determine the identity of some of the mystery properties that are displayed for your dates. If you decide to use Priceline, you can post back and someone should help you formulate a bidding strategy, but first you'll want to make sure you're familiar with Priceline by reading through their "Terms and Conditions" and by reading THIS POST. As far as whether or not hotel rates will come down for that time frame, I really don't know. Perhaps someone else has an opinion on that.