CardiffBaseball: If you don’t mind dropping the jingle, Morton’s downtown is good. You’re right, though, about the steak not tasting $50 better.
While getting a great steak at a chophouse is a fun experience, you can do nearly as well at home on the grill.
Buy a nice cut of meat (I like boneless ribeyes), use some olive oil and steak rub (you’ll want to do this a few days in advance) and then BBQ. Strangely enough, Costco has excellent steak rub. It’s cheap at $5, and you find it in the seasonings and spices section.
If you’re ever in Chicago try Ditka’s. I was there recently on business and had an excellent steak. Completing the “Former NFL Coaches Who Now Have Steak Joints” circuit: A buddy of mine swears by Shula’s in Miami.