Bar of the month

Jack’s and 404 Wine Bar
2852 N. Southport

The Basics
Where you’ll find it: 2852 N. Southport, just north of the Southport/Diversey intersection. (773) 404-8400. www.jacks404.com

When it’s open: 5 p.m.-2 a.m. Monday through Friday; Noon-3 a.m. on Saturday; Noon to midnight on Sunday.

Peak time: Jack’s gets a consistent late-arriving dinner crowd, usually between 7-8 p.m., and is busy on weekend evenings. In the summertime, get there early to reserve a spot in the beer garden.

What you’ve heard: A very comfortable setting with the best of both worlds — an upscale sports bar on one side and a cozy wine bar on the other. ... Easily one of the best beer gardens in the city. ... Hardly your average “pub grub,” as Jack’s has a number of delectable items on the menu. ... Friendly service and a fun, neighborhood bar.

History in short: Phyllis Carlucci, the current owner, bought Jack’s (formerly The Black Cat) in 2000 and completely redesigned it. The 404 Wine Bar is modeled after a lounge in Paris.

Visual Aids
First impressions: There is a warm, candle-lit vibe and great holiday lighting. ... The bar is immediately to your left upon entering, and the bartender always seems to be greeting you with a smile. ... There are a total of five TVs in Jack’s and the adjoining middle room for you to catch the game, and the 404 Wine Bar has the feel of a lounge, complete with two fireplaces, leather couches, jazz music and tables perfect for small groups or couples. ... The music is great and never overwhelming to where conversation is difficult.

The atmosphere: Some people like to consider Jack’s and the 404 Wine Bar an extension of their home, and it’s easy to see why with the relaxed, unpretentious charm. ... Jack’s is like an classy neighborhood sports bar, while the 404 provides a more intimate setting that would be great for a date or to catch up with friends over a glass of wine. ... The popular beer garden off the back exudes class with its canopy of white lights and outdoor restaurant feel.

What you’ll tell your friends: “What I love the most is that they really seem to appreciate if you’re enjoying yourself. Surprisingly, you don’t get that everywhere. And I love the fact you can get a pint and watch a Cubs game on one side or slip over to the 404 and have a quiet glass of wine.”
— Elizabeth

What the owner thinks:
“I think both Jack’s and the 404 Wine Bar have the components of a warm atmosphere, great American comfort food, good music and a genuinely friendly staff that cares if the customer has a good time and pays attention to all the details. Basically, there is something for everyone here.”
– Phyllis Carlucci

The Experience
At your service: There is never a shortage of staff members, as bartenders and waitresses are in a steady supply, and a manager is always on hand. ... The food and drinks arrive swiftly, even when the place gets busy. ... One of the best traits of Jack’s is the greeting you get at the door and the smiles all around. They make it a point to hire the friendliest people, and it makes a difference. ... And trust us, they know their wine.

Get your drink on: A full bar offers plenty of mixed drink options, and they take the wine and beer selections to another level. A choice of 11 beers on draft, including favorites like Guinness, Bass, Goose Island 312, Hard Core Cider, Fat Tire and Blue Moon, as well as 16 options in the bottle, such as Red Stripe, Amstel Light, Summit Thunderdead IPA, Widmer Hefeweizen and, just added this month, Delirium. At the 404 Wine Bar, you may not believe the extensive variety of red and white wine at your fingertips. They even rotate the flight samples every six weeks so you can get a taste from different countries around the world (currently France). And don’t forget the martini list.

Menu variety: This is another area where the folks at Jack’s and the 404 Wine Bar separate themselves from other bars on the North Side. The grill’s specialties include Judy’s homemade chicken pot pie, grilled pork chops with mashed potatoes and mustard cream sauce, baked macaroni and cheese and steak sandwiches, but the good news hardly stops there. Try appetizers like calimari or quesadillas, plenty of soup and salad options, sandwiches like the turkey club or blackened chicken, gourmet pizzas or perhaps you’re in the mood for Jack’s signature half-pound burger with cheddar, sauteed mushrooms, bacon, sliced avocado and topped with onion rings. An important thing to remember is that you can order whatever you like off the same menu from both bars or the beer garden.

Daily specials: Monday: $3 Guiness drafts and $5.95 Margherita pizzas. Tuesday: $3 Stella drafts and $5.95 pepperoni pizzas. Wednesday: $3 Blue Moon drafts and $6.95 BBQ chicken pizzas. Thursday: $3 Goose Island 312 drafts and $4.95 nachos. The Beer of the Month, at $3 a pint, is currently Sam Adams Winter Lager.

Who you can expect to see there: Jack’s caters mostly to a lot of young professionals in their 20s and 30s, while the 404 Wine Bar attracts a lot of people on dates and is ideal for a girls’ night out. Families often stop in for an early dinner and spend some time in the beer garden when the weather is nice.

It’s a good spot to … “enjoy one of the best-decorated beer gardens you’ll find anywhere. It really feels like you’re in Europe. ... meet friends or a date and get treated like royalty. ... enjoy the freedom of having two distinctly different bars in one. ... enjoy an incredible home-cooked meal, not just a bite to eat.”

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