Chicago is known as a steak house town, and lord knows you have plenty from which to choose. But when you want to get both your turf and your surf on, then you simply must head to Joe's. Located in the heart of downtown and bustling with old-school vibe, the place will have you sipping your drink and thinking Sinatra might walk in any moment. The gentleman at the host station (he'll be sporting a green bow tie), announces that your table is ready, and the staff has you tucked in and ready to kick off the night before you can say "Jack the Knife."
You can't go wrong with anything on the menu, but having been there too many times to count, might I suggest the stone crab claws (fresh daily) with the in-house mustard sauce. Follow this with a fresh seafood entree, or perhaps one of the prime-cut steaks that hold their own with the best of 'em. Pair it up with some vino, and you have yourself a fine evening. You'll be humming "I Did It My Way" all the way home.
Local tip: reservations are strongly recommended, but you can get lucky in the bar area and snag a hightop table that'll work just fine.