Matchbox in Chicago is the four-foot-wide West Town cocktail bar on Milwaukee serving stiff classic cocktails until 02:00, a 30-seat triangle since 1995, cash only.
Tip: Cash and glass only. Order an Old Fashioned; the slim bartender pour is the house standard you do not modify.
Address: 770 N Milwaukee Ave, Chicago, IL 60642
Au Cheval in Chicago is the West Loop diner-bar on Randolph that runs the full menu until 02:00 nightly, with the country-famous single-with-egg cheeseburger.
Try: Single cheeseburger with egg
Tip: Sit at the bar past midnight; the queue clears at 23:30 and the kitchen runs the same menu without the dinner wait.
The Wieners Circle in Chicago is the Lincoln Park late-night hot dog counter on Clark, with char dogs, cheese fries and staff-customer banter past 02:00 on weekends; Friday and Saturday close at 04:00.
Try: Char dog with everything, cheese fries
Tip: Char dog with everything; the chocolate milkshake is the closing order for the walk back up Clark.
Ghareeb Nawaz in Chicago is the West Ridge Pakistani halal counter on Devon, with $7 chicken biryani open until 02:00, the only Devon plate at that hour of night.
Try: $7 chicken biryani special
Tip: Cash only. Bring a container; the biryani plate feeds two with leftovers for the morning.
The Aviary in Chicago is the Achatz-Kokonas modernist cocktail bar on Fulton Market with a 21:30 late seating, edible-ice cocktails and the Office speakeasy below.
Try: Modernist cocktails
Tip: Book the 21:30 Wednesday or Thursday seating; the room is at half capacity, the cocktails come faster.
Ramen-san in Chicago is Lettuce Entertain You's River North ramen room on Hubbard, open Thursday to Saturday until 02:00, with tonkotsu and the spicy garlic bowl.
Try: Spicy garlic ramen
Tip: The spicy garlic ramen at 01:30 is the call after a Loop show. The pork bun on the side is the wing.
