Druckin Fat & Happy in Chi-town

I spent most of my time in Chicago chasing after my nephew, eating pizza, Harold’s fried chicken and Fannie May buttercreams (thanks, Mom!), and, perhaps not surprisingly, packing on the old lbs. When you find yourself pining for a vodka martini as a caloric respite from food, you know you need to get to a bar ASAP. This is the bar we chose:


Oh, how I love this picture. It looks cold and stark and urban and the trees are little sticks and the sky is gray and it’s still daylight, which means it’s probably 4:00pm. Perfect time to duck into a pub, warm up and get your drink on.

You're getting warmer.

Of course, it’s May, so it was a warm-ish night. Awesome pals Ali, Heather, Christina and MJ sat out on the patio with me, chatting about everything and nothing at all. (As you do.) Jack’s Bar & Grill is connected to 404 Wine Bar, and I’m not quite sure why it’s not just one big bar that grills and serves wine — I sense that Jack is having a minor identity crisis.

That said, it’s a great place to meet and (so I’m told) eat. There are grown-ups there. You can hear yourself talk. It’s got big circular booths within shouting distance of the bar, and I think there’s even a fireplace inside somewhere, making it a cozy winter option. Plus, the neighborhood is easy cab-distance to both Lincoln Park and Wrigleyville — and stumbling distance from one of my favorite Chicago dining options, the famous/infamous Golden Apple:

Thanks to Jeff B from Good to Grub! Golden Apple krinkle cut fries. FOUL TEMPTRESS.

Two words: PIE CASE. Two more words: PATTY MELT. (See why I can’t fit into my jeans?!) The Golden Apple is open 24 hours, and the some of the staff have clearly been working there since they opened over 40 years ago. NPR even did a special, 24 Hours at the Golden Apple. So you know it’s good. But tempting as it was, I did not eat the Apple this time. After we closed down Jacks at 2am, we honored another great Chicago tradition, the late-night burrito:

Janitzio's -- I love you, man.

Ah, Janitzio’s. When I have no one to go home to (or with), you are always there for me, with a cheap ‘n cheerful quesadilla or burrito and plenty of drunk dudes for me to flirt with, drunkenly. So that’s one Friday night in Chicago. Still my kind of town.



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4 responses to “Druckin Fat & Happy in Chi-town

  1. John P

    Funny how our lives are always crashing (not that I am complaining). Did you know that I was once a doorman at Jack’s/404 winebar. Let me tell you that the food is as good as the vodka, there is a fireplace to warm your cockels or anything else you need warmed, and the patio is as cute as, well, me. Glad you had a good weekend.

    • debra

      ohhhh i’m afraid i must take issue with this comment, my good man: NOTHING is as cute as you! tho i’m willing to believe that jack’s patio comes close. 😉 i love that neighborhood. would’ve been even BETTER if you were there with me. hope to see you and yer mrs very soon in CA!

  2. Phil Brody

    before I lived in Bucktown (my final CHI apt), I lived right around the corner from Jack’s — lived on Wolfram. Jack’s used to be The Black Cat and was a great local dive. Love Jack’s (and 404), but also miss the Cat.

    ah, Chicago…if only it was sans winter…I’d probably still live there.

    • debra

      i am with you on the winter, tho i do get all misty-eyed and nostalgic for it sometimes. nothing compares to the comfort and camaraderie of a warm pub on a cold day. that said, hiking in malibu when it’s 70 degrees and sunny in january doesn’t suck, either. 🙂 thanks for reading! love hearing about your chicago exploits. keep em coming!

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