| Staying downtown will be pricey, but it's WELL worth it. Especially if you aren't familiar with the city. Plus, some hotels include parking as part of your stay. Expect to pay around $150-250 a night, and parking (if not included) could be around $30-50 for 24 hours.
Get a lot though, your car will be safer, and you will avoid any unnecessary ticketing.
Any "cheap" hotels you might find anywhere outside of the loop can be bed-bug ridden crack houses. Up where I live, just North of Wrigleyville, you can find a hotel for $59-$100 a night, but you WONT want to stay there. Trust me.
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