I had the distinct displeasure of being forced into Tavern on Rush...endless terror in a city filled with gastronomic excellence. One course was a bland fish hidden underneath a pile of seemingly unwanted boiled groceries, presented on a block of wood.
People in Chicago say that deep dish is a must for first timers, but I don't know...first time I was in Chicago, I did the Pizzaria Due's Numero Uno Medium, and passed out after 1 slice. You have been warned!
Any guidance on the dining party? Guys night, client dinner (how many), date night, family outing, etc - makes a difference.