Where to Go If Eating Alone?
Personally, I've found that I can eat just about anywhere alone, and most restaurants welcome it. It's up to you to decide whether to eat at the bar, or have your own table; I generally prefer the latter, but restaurants are generally happy to accommodate you either way. So pretty much all of the usual advice on where to eat applies to solo diners as well. For an overview, you might want to check out the topic at www.chowhound.com/topics/457215
One restaurant in Chicago that may be particularly suitable for your needs is Avec. Avec specializes in "small bites" and the food is excellent, there as well as its sister restaurant next door, Blackbird. What makes Avec particularly appropriate for solo eaters is that (a) they don't take reservations, and (b) they feature communal seating. So if you're alone, even at prime times, you won't have to wait for an entire table to open up; they'll seat you wherever there is an open seat. Yes, you'll have the company of strangers for your meal, and you'll probably enjoy it and be welcomed by your dining companions as a friend. Avec is located roughly a mile west of your hotel. www.avecrestaurant.com
BTW, the street name is spelled Wacker. (Al Capone is long gone! ;) )