I bought the aforementioned cookbook (Will It Waffle?) last year and have found it to be interesting. By far, the most successful recipe has been the fawaffle - in fact, that’s what’s for dinner tomorrow night. The regular waffles are pretty darn good too. The chicken parm, waffled meatballs, and sandwiches were good but not awesome. And having recently been introduced to bibimbap, I’m excited to give that recipe a try.
As far as other options, this is a pretty good deep-dish-style pizza: http://www.thecollaboreat.com/deep-dish-chicago-pizza-waffles/