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Originally Posted by lunchbox
to get back to everyone, we are planning on driving so it doesn't necessarily have to be downtown that we're staying, which is why i mentioned the bit about the train system, if i have to stay at one of the airports and train it into the city every day i wouldn't really mind if it's cheaper.
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If you don't mind taking the Metra train into town everyday, I'd suggest the Schaumburg, O'Hare, or Northbrook areas. You can get 3 - 3 1/2 star hotels thru Hotwire for as little as $45/night. Hotel parking is free in those areas as well, which can be $20+/night at a downtown hotel. This is the only way our family of five does Chicago anymore. We used to stay downtown thru Hotwire hotels, but even Hotwire has had trouble getting good rates near Michigan Ave for the past few years. I've stayed in all the above suburbs and never had a disappointing hotel.
Northbrook and the O'Hare areas don't offer much to do, but a short, 10 minute drive will find you damn near anything. The Schaumburg area has a monstrous mall with all of the national chain restaurants to go with it dumped in one area, so that can be convenient. If you like Sushi, try the Todai Sushi restaurant in the mall... it's killer.
The train ride to downtown from these areas is 30-40 minutes, but it costs next to nothing, especially if you buy the unlimited weekend pass for like $5 (
http://metrarail.com/tickets.html). Look at the
MD West line for stops and times to downtown from the Schaumburg or O'hare areas. Look at the
MD North line if your in the Northbrook area.