AlexF

It could be the Wyndham, Crowne Plaza or Omni. It could also be the Palomar or Sheraton which are a block or two from Michigan Avenue. At that price it's probably not the Intercontinental but it could be. And it may be the W but it's on the lake shore and about a half mile from Michigan Avenue.

How much does it cost to park your car at the Palmer House? I couldn't find any info on their site. Is it the standard $50 or so per day? If so, then I would probably save some money and park at the Millenium Park lot.

Some of the hotels south of the river around Millenium Park aren't bad although a lot of the restaurants and shops are north of the river around the Mag Mile area. The Red Line is two blocks from Michigan Avenue and can be picked up in the Millenium Park area and Grant Park area. Parking at hotels is usually around $50 a day especially in the Mag Mile area. You could always take the train in but if you have lots of luggage, it may not be that fun plus if you buy stuff, you're going to have more bags when you leave.

I've stayed at the Blackstone before. It's a nice hotel and close to Buckingham fountain. The Red line isn't too far away which you can take up to the Magnificent Mile. You could also walk as it's a little over a mile to the river.

Under $100 in the Loop in Chicago is possible although that is more in the summer. I would keep checking back every week to see if you can get a room for under $100. I've seen rooms this summer that were around $85 in the Loop and on Michigan Avenue.