OK Idle Thoughts Here’s the skinny.
From Summit, you can take the Heritage Corridor train. It will roll you from Summit, right to the Jackson/Van Buren station. Take it. It will save you MAJOR cash. From there, get your free museum days lined up, and hit the museums.
If you’re in the mood to just walk and see the sights, there’s no better place to do that than the Mag Mile (as has already been mentioned). It’s what to see while you’re here. In fact, if you can catch the double deckers, you can do the whole hop-on hop-off thing as you choose, and see most of the downtown stuff on one or two days.
The real Chicago though, is in the neighborhoods. Get a Bus schedule after you look at the map here and go. Neighborhoods like The Near South Side, Chinatown, University Village, Lincoln Park, Uptown, Lakeview, Roscoe Village, Bucktown and Wicker Park are the places where the REAL Chicago lives, and is still safe for a wide-eyed tourist such as yourself.
The bus goes everywhere, and is fairly cheap.
Go to Metromix for all of the neato stuff to do in these areas. You’d be suprised at how much you can actually DO on a tight budget.
So, if you’d like some precise recommendations, where to eat, what to see, just shoot me an e-mail, I’d be more than happy to give you some suggestions.