Most states have made drinking alcohol at home illegal due to the proliferation of home facial-tattoo machines. Enjoy alcohol in public with today's deal: for $20, you get $45 worth of pub fare, upscale Italian cuisine, wine, and beer at Jack's Bar and Grill and 404 Wine Bar, located in Lakeview on North Southport Avenue.
Jack's Bar and Grill, a neighborhood sports bar, and 404 Wine Bar, an upscale dining area, peacefully co-exist under the same roof. Contained by a vintage building reminiscent of an English pub, old friends share intimate glasses of wine by the fire in 404, while Bears fans watch games over mugs of craft beers on tap in Jack’s. Settle in front of the game and order up comforting fare such as chicken wings ($8) or the much-beloved chicken potpie ($12) from Jack's menu. On the other side of the unguarded border, 404's menu offers sultry Italian specialties, including a la carte cheese and charcuterie ($5–$6 each) and upscale entrees such as quail eggs and ham––la querca heirloom ham, manchego, and fried quail egg with crostini ($10).
In the spirit of conflict resolution, you can order from both menus regardless of where you choose to sit. In the beer garden, white lights twinkle overhead, while 404 offers cushy chairs or tables for two. Conversation ranges from light to rowdy, but is always spoken aloud in the spirit of friendship, and never the condescending, silent pantomimes of grease-painted, stripe-sweatered charlatans. Reservations are preferred.
- We each had a great glass of red wine and split a dessert, sitting by the fireplace. So nice and quiet and intimate. – Tempe T.
- I love their menu - simple and easy to pair wine with. I completely recommend this place for a first date or a girls night out. – Christina P.
- The wine flights are great, as is the food, especially the chicken pot pie. I know because I think for 4 straight nights I ordered pot pies at 4 different bars. It just happened that way. – Phil H.
2856 N Southport Ave.
Chicago, Illinois 60657Get Directions