Chicagoans can argue for days about who makes the best pizza, but the Zagat survey puts Uno and Due at the top (they're basically the same restaurant, it just got so popular they opened a second branch across the street from the first), closely followed by Home Run Inn and Original Gino's East, then Carmen's and Edwardo's. Knowing Romans, I suspect your friend would find all of those places wanting in comparison with Baffetto. He will likely be more impressed by the quality and low price of steaks.
Chicago, IL