hahaha---faster than I should

I'm also pretty bad about measuring time accurately--but I drive it a lot and if it's not rush hour, seems like it doesn't take much longer than 30-40 minutes or so from downtown. Now from O'Hare, that's another story. And if he's picking up at Midway, the downtown suggestion doesn't make sense either since they'd have to back track.
Called to check and the restaurant at Horseshoe is definitely still a smoking facility--in fact, it is now 21+ only to enable them to do that.
No idea if that steak is still on the menu at Giovanni's. I have eaten there frequently and for years and while it has other things on the menu, I've never had anything outside of the basics that I felt was very good. Certainly only one person's opinion.
Not a fan of Borgia's at all. Three Floyds is probably the best of the bunch but likely NOT the atmosphere you're looking for...
I'll also add that Borgia's is pretty far (west? south?) on Calumet Ave--not really convenient to Gary. Giovanni's or Jack Binion's, if you can deal with the smoke, are probably your best options based on location.