If you search on Hotwire.com for your dates, there is a 4.5* hotel in the Mag Mile/Streeterville area for $114 (your price may differ slightly) and a 4* in the North Michigan Ave/Water Tower/Gold Coast area for $99.

Hotwire is a deep discount/non-refundable service where you find out the hotel after purchase. Either way, both hotels are in your price range and definitely more upscale properties.

never used Hotwire, often looked at the site though when I was planning trips to NY!

Maybe I'll give it a go :-) Always a bit suspicious when you don't know the hotel you are paying for!

www.betterbidding.com has Hotwire bidding tips and hotel lists.

that's really helpful, thank you Dave!

We've always had great luck with Hotwire, as long as your dates are etched in granite. I was surprised last December that there was such a good offering. We got the Intercontinental for $99.00.I think the biggest factor in the offerings is whether any large conventions are in town, and I guess most don't go in December. It's a great time to get a great deal, and if you're going for a full week, that's a signifigant savings.If you're nervous, stick to 4 star. How can you go wrong?

If you're accustomed to "budget hotels", I don't think you'd find anything 4* or better through hotwire that would make you unhappy, as long as you're careful to stick to the zones where you want to be staying.