Recently stayed at the Westin Michigan Avenue for a conference. Great location for walking to restaurants. Mrs. Tull was able to get her shopping fix in spades while I was in meetings. Also only a few blocks from El stop that will take you to Wrigleyville, if that's in the cards.
i pricelined the Wyndham back in 02 for around $100 seems like. it was pretty good and a great location. i called the day before and they quoted me $279
$30-40. i wouldnt rent a car either, the hotels downtown will rip you a new one for parking.
you could also take the blue line train from ohare and walk a few blocks up to NMA if you dont have much luggage. i think its only 2 bucks. i took the orange from midway a few months ago and walked to the hotel, it wasnt too bad. although, i just had a backpack.
I just booked The Drake for 3 nights. Got it on priceline for a bid of $135. I started bidding last week on Priceline for 4star in the North Michigan Avenue area starting at $110 and never got accepted (even doing the rebid technique and waiting 24hr). But got The Drake today at $135.
The Drake is classic Chicago at it finest. I stayed there for the Texans vs. Bears game in 2004 (?) which was also the weekend before Christmas which is a damn fine time to be in Chicago, unless you hate cold weather. The rooms are older and show a bit of wear around the edges, but that's part of the charm. Seriously, if you don't like The Drake at $135 something is seriously wrong with you.
If I'm bringing a chick to Chicago, The Drake is my number 1 choice. If it's business (just me), the Sutton Place is better.
I stayed at the Drake a few years ago and really enjoyed it. I was lucky enough to get a room upgrade, and the room was huge. There were a number of good bars and clubs within walking distance.
The Palmer House is cool in a historical kind of way, and they're renovating the rooms (which desperately need it), so I'd give it a year before going back.
The service at the Palmer House sucked, however. We went down to the hotel bar and my fiancee ordered a glass of the house pinot. First, the bartender empties the dregs of one bottle into the glass, and then opens a new bottle and pours some of that into the glass. And mind you, it wasn't a particularly fair poor--it was no more four ounces than I am Mickey Mouse. LonghornLawyer-ette questioned him on this, but he just shrugged his shoulders and handed her the bill: $18. For the house pinot. Seriously--$18 for a friggin glass of mediocre California pinot. That is half full of the dregs of another bottle.