We the architectural river boat tour about 3 yrs. ago. It was suggested by another person in our group. Thought I was being a good sport by going along. It was great.
Also did Wrigley. As a baseball nut and historian, it was a much. Hit a little Irish pub for a pre-game meal.
My restaurant rec would be the Greek Islands. Old school Greek place located next to the Billy Goat Tavern, the inspiration for the famous cheeseburger cheeseburger SNL skit.
Might have her get a tip on an old school Italian place.
Definitely want to do Chicago again.