Re: Chicago Trip
Priceline name your own price is always great for me. I live in the Chicago suburbs and use it often when we go downtown for a night. Can usually get hotels for 60-70 per night during the winter and 90-100 during the spring/summer. I usually take whatever priceline says is the average and try for about 60% of that price for an initial bid. Then use multiple credit cards and email address between my wife and I to try and bid up slowly on the same bid criteria.
I'd target staying in the Grant Park or River North areas. All the hotels there should be a decently close walk to the red line which gets you most places you need to go.
And if worse comes to worst you can always stay up by O'Hare. Lots of 3-4 star hotels that are really cheap via Priceline bids on weekends. The blue lines goes in from up there to the city and isn't too bad of a trip.
Let me know if you have any other questions! I use priceline a ton and have lots of experience in downtown Chicago with hotels and neighborhoods.