Has anyone out there had success with booking good 4* accommodation in Chicago with the priceline.com site? What sort of prices did you get?
And if I try bidding, should I start now for March? Or wait closer to the time if Chicago hotels are likely to be quiet at that time of year?

Checkout this site

http://pub4.ezboard.com/bpricelineandexpediabidding

There you can find lots of info. and people who can help you.

I bid 3* on a very busy weekend in August and got a $69 rate at the Westin on Michigan Avenue. We were shocked, but happily cancelled our $209 Hyatt reservations. Really liked the Westin, which has been remodeled recently. We did bid two days prior to arrival, so perhaps that's one reason we got a good rate.

Last week, we stayed at the Hilton (On South Michigan Avenue) for $50 via Priceline. It was a Sunday nite - I'm sure that helped. Hotel is very well-kept (tho I don't much like biiig hotels) and room was large and comfy. Unfortunately, we were driving - and the garage rate was $22! We've also stayed in the West suburbs for as little as $25. As it happens, I'm killing time here right now - waiting for word on my latest P'line bid, for Christmas nite. Will let you know if it comes thru with anything good.

I got the Westin River North for $83.00
per nite in October. Really great hotel!
Made me a priceline.com believer