Re:Any good places to eat in and around Madison?
For Chicago hot dogs Poppa's on Buckeye Rd. in Madison has always been my favorite, but it's been awhile since I've been there.
There's a Rosati's Pizza on the far east side of Madison. Glass Nickel Pizza has a Sun Prairie store and while it's not Chicago-style pizza it's still very good...well, I like it anyway. If your friend and her family like Edwardo's in Chicago then they should try Pizza Extreme.
A coworker of mine lives in SP and she speaks highly of Gus's, which I understand to be a former 5-and-Diner that reopened as an independent. The Pancake Cafe in SP serves up a good breakfast.
Sadly, though, White Castle is nowhere to be found.