Where to drink well in Chicago by the glass and the bottle: natural, classical, and worth the cab fare.
Wine bars in Chicago. natural, classical, and the grower-focused rooms worth the cab fare.
The Loyalist in Chicago is the wood-bar room downstairs from Smyth on Ada Street, an unfussy wine bar from John and Karen Shields with the cult dirty burger.
Signature pour: The dirty burger with a Beaujolais by the glass
Wine focus: Lo-fi natural wines, deep Burgundy
Food: Burger, snacks, full kitchen
Tip: Walk up to the bar at 16:55. The dirty burger is on the bar menu from open; it leaves the kitchen rare and griddle-pressed.
Webster's Wine Bar in Chicago is the long-running natural-wine bar that moved to Logan Square on Milwaukee Avenue in 2014, with a 200-bottle list.
Signature pour: Biodynamic flight by the glass
Wine focus: Old World, biodynamic, small producers
Food: Cheese and charcuterie boards
Tip: The Monday-night flights are themed around a single region; the next-day discount on full bottles is a real value pull.
Rootstock in Chicago is Humboldt Park's neighbourhood natural-wine bar on California Avenue since 2011, with a small-producer list and a strong charcuterie board.
Signature pour: Cab Franc from the Loire by the glass
Wine focus: Natural wine, small importer focus
Food: Small plates and a strong cheese board
Tip: The kitchen runs late; the burger and pork-rillette plate are the late-night moves once the cheese case thins.
Maria's Packaged Goods in Chicago is the Bridgeport corner store-and-bar on 31st Street: hybrid bottle shop, neighbourhood pub and Kimski Korean-Polish kitchen.
Signature pour: Marz beer with a kimchi-pork dumpling
Wine focus: Cult Midwest beer, natural wine
Food: Kimski Korean-Polish street food
Tip: Kimski's kimchi pierogi and the Marz brewery beers on the back wall are the room's defining pairing.
Peak food season in Chicago is year-round.
Local dining hours: lunch around 12:30, dinner from 19:30.
service is typically included; small extra is welcome but not expected.
Ask the next local you meet what they would order. Chicago rewards trust.