Where to go? plz help?

Yea a park or better yet try a forest in the west part of Illinois.

deep sky is out of the question anywhere near Chicago, but I was just north of Chicago (inside the landing path of an airport) yet the skies were plenty dark enough for clusters and planets.

there's an old saying in the Navy, carry an oar inland until someone asks you what that thing is on your shoulder, retire there.

works the opposite for Chicago... carry your telescope north until someone says "Hey, a Dobsonian! Cool!" and you are far enough away.

I'd strongly recommend joining the local astronomy club, as they will have all the best locations checked out, and there is safety in numbers while observing in an urban setting:

http://www.chicagoastro.org/

When I was living in downtown Toronto, I did most of my observing in my back yard, where convenience and safety were more important than dark skies.

If you want to find a dark location on your own, this map of light pollution in the Chicago area is a good place to start:

http://cleardarksky.com/lp/Chicagolp.html?Mn=astro...

A big park is a great place, so long as its not too illuminated there.

ask local astronomers. they will know where good places are.