Chicago's downtown grid under the elevated tracks. Lunch counters serve the office crowd; Italian Village has run since 1927 and Lou Mitchell's since 1923.
Pizano's Pizza & Pasta in Chicago is the family-owned Loop deep-dish room founded in 1991 by Rudy Malnati Jr., son of Pizzeria Uno's original cook Rudy.
Signature: Cheese deep-dish, Thin pepperoni
Order: The cheese deep-dish, no toppings, the way Rudy Sr. baked it at Uno.
Tip: The Madison location is the original; State Street is the bigger pre-theatre spot.
Buddy Guy's Legends in Chicago is the South Wabash blues room the man himself opened in 1989 and where he still plays a residency every January.
Tip: Closed Monday and Tuesday. Wednesday and Thursday close at midnight; weekends run to 01:30. Cover usually $20, kitchen serves Louisiana barbecue.
Cindy's rooftop in Chicago sits on the 13th floor of the Chicago Athletic Association with all-season terrace seating that frames Millennium Park and Lake Michigan.
Tip: Weekends fill from 21:00; reserve via OpenTable or arrive at 16:00 for the sunset window. The terrace stays heated and open year-round.
LH Rooftop in Chicago crowns LondonHouse on the corner of Wacker and Michigan with three tiers of terrace facing the river and the Trump Tower clock face.
Tip: Open every day until midnight, food last call 22:00. The top tier is the photo spot; weekend brunch from 11:00 is the easy walk-in window.
Milk Room in Chicago is the eight-seat micro bar above Cindy's at the Chicago Athletic Association, pouring rare vintage spirits selected by Land and Sea director Paul McGee.
Tip: Tock reservations only. Sunday through Tuesday close at 21:00, Wednesday through Saturday at 23:00. Eight seats, no walk-ins.