I am planning on extending a business trip for this weekend in April, but I cannot believe the prices I am seeing! Anything nice is at least $200, and where I had hoped to stay is close to $400/night! (The Drake, Hotel 71)
The Wyndham is sold out for those dates, as is the Sheraton, Raddison, and Palmer House. What is going on that weekend? Opening Day? That is usually on a Monday, isn’t it?
I could stay in luxury in Manhattan for less than what I am seeing in Chicago for that weekend.
Where are you looking? A check of travelocity.com shows the Wyndham Drake as having available rooms for $85, the Hilton Drake around $170.
There are motel6-type ratholes shown available for around fifty smackers. Perhaps the web gods were being cranky and playing a trick on you…?
Chicago is a huge, HUGE convention city. Some weekends are extremely busy with a few big hotels being almost completely booked for conferences, and then everyone else being pushed out to other hotels. In short time, everything is quite booked and any remaining rooms are expensive.
That said, I am often looking into Chicago hotel prices. After checking all the “hotel discount” sites, I’ve often found the best rates for Chicago hotels on Expedia.
Last May, my friend an I went to some Cub games…in using Priceline, my buddy entered $90 for the downtown area, and it instantly came back accepted by the Millenium Knickerbocker…after we were accepted by Priceline, we went to other travel sites, and the lowest rate we could find was $185…he should have started much lower than $90 when bidding, but it was his first time…if the weather is nice, shouldn’t matter where you’re staying if you’re familiar with the CTA. . .
I should have been more specific. I want to stay downtown, and not have to use any sort of transit other than my feet to get around and see the sights.
I do this quite often, if I stay over a Saturday night, I can use the savings on plane fare (~$100) for lodging. I’ve done it in the past 12 months in LA, D.C., Boston, and Las Vegas, and never paid more than $125/night for a nice hotel (I like Wyndhams). I have looked at all of my favorite spots on the web and can’t find anything comparable for even twice that rate.
Anyone know of a cool boutique type hotel Downtown that wouldn’t show up on the big commercial sites?
I’ve found $52/night for a boutique hotel on Chestnut (which name I cannot remember) in the Watertower District (north end of Michigan Ave.) on www.hotwire.com. I’ve found this rate twice at different times of the year.
That’s the weekend of K-BIS, the Kitchen and Bath Industry show at McCormick Place. It is always a jam packed affair with tons and tons of visitors, especially a lot of drive ins from the surrounding 3 state area.
I get that Friday off to go so I’m cool about it. 
Good luck finding a hotel room, check out Chowhound for eating recommendations.
I used to deal with this service, they always seemed to have decent rooms at decent prices, especially for last-minute reservations.
Lamar, if you’re in for a bit of history and a great location, head to the Allerton. Trip advisor puts prices for that weekend between $94 and $324.
It’s right on North Michigan, between Huron and Superior in the heart of the shopping district and right near River North, while you’re here, head to Fogo de Chao, and/or Opera for dinner, excellent and very different experiences. Or if you just want a damn fine steak, Ask the Concierge to point you to Gene and Georgettis (it’s on Franklin) or Gibsons. If you’re into Jazz at all, head up to north boradway and visit the Green Mill, an excellent venue, and the oldest continuously running jazz club in the country. One caution though, don’t pay for parking at the Allerton, you can do better on the street.