You should not take her out to dinner. It will set you up in the most awkward situation possible, and you will be required to speak constantly. Avoid it, if you want to make your life easier. If you're intending to be in downtown Chicago, Millennium Park and Grant Park would be good places to go, although you would want to do something else. You might try the Moonstruck Cafe nearby on Michigan Avenue, which has wonderful chocolates. Also, don't take her shopping with you, unless you're planning to visit all of the chocolate stores near the Water Tower Mall, or something of that nature. She will not be interested in buying things with you, and especially not clothing. The Lincoln Park Zoo would also work well, as it's fairly close to downtown and free, so it won't matter if you and your date decide that you suddenly aren't interested.