Originally Posted by nmculbreth
I've had good luck with Priceline. The last time that I went to Chicago for the weekend I ended up at the Hyatt Regency and if memory serves correct I only ended up paying around $70 a night after taxes and surcharges. Parking was ungodly expensive, but that is sort of to be expected.
Depending on how far you're willing to walk and how often you need to access your car, 500 W. Monroe garage offers all day Saturday/Sunday parking for $6/day. I haven't found anywhere else to beat it. Especially during the summer it's right next to Union Station and the water taxi that will take you over to Michigan for a few bucks per person. Nice trip down the river and great for out of towners to see a little of the city without paying $30-40 for a city river cruise.
Also, the Prudential Plaza is 2-3 blocks from that Hyatt and offers weekend parking for $12/night (last time I parked there was last winter so it may have gone up). Sure beats that $50/night at the Hyatt.
And if you need parking in the River North area check out this garage - http://www.greenwayselfpark.com/buyonline/
. Cheap advance purchase parking for a night out in that area.