Yes, and a lot. but not cheap
Yes, if your in a hotel they usually have parking. Other than that you will pay dearly. Public transportation cheap; bus, the L or an Uber.
Yes. Multiple parking lots on surrounding streets. No underground parking from what i could tell.
All of above ~ yes, AND expensive! Use public transit, cheaper and easy to use.
Yes, but you'll pay for it. True hostel types will take the train downtown and leave their car in a suburb.
There is, but it's expensive
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