Hy's
Caesar's
Nick's
Smuggler's Inn
The Keg
Vintage Chophouse really struggled with our large party last time I was there, and they gave me a well-done steak even though I ordered medium-rare, and the waiter insisted it was medium rare and wouldn't exchange it.
Might be better with just two people though.
I've never been to Chicago Chophouse. I've heard so many bad things about it I've avoided it like the plague.
Ric's Grill sucked, BTW. My steak was cold for some reason.