If you take the route I mentioned above, you should be fine.
I was thinking you were going to take 57 north to 90/94 through Chicago to 90 to Rosemont.
Don't take this route cause this is where you'll be driving through the "bad" areas.
I get you but we may be needing to get off the interstate at about that time.
I'm doing either 57 or 55 to 294.
Do you think 57 is safer / better than 55 at that time of night?