Chicago: Where to go

Redhead-LogoYou may have figured out by now that I am not a big fan of parties… and certainly not big and loud ones.  So when I go to an event like Microsoft Ignite (as I did in May) I tend to shy away from the evening events,  in favour of smaller dinners and pubs.  If I find a place with the right ambiance, a decent scotch list, and where I can smoke cigars, well that is where you are likely going to find me… if not every night, then a few of them.

I have a partner in crime for these evenings.  Brian Blum and I have been seeking out these places for a couple of years, and this year it was he who called me Monday during the day and said ‘I found our place.  We’re hanging out at the Redhead Piano Bar on West Ontario Street tonight.  Ok, I’m in.

I should mention that while I often find the player at piano bars a bit cheesy, I almost always prefer them to the loud thumping music that is the norm at most clubs, which is only one of the many reasons I don’t enjoy those big parties and club atmospheres.

Redhead-1I knew I was about to step into my kind of place as I approached the door, where the doorman (who I would later learn was the famous and fabulous Jimmy) was politely refusing entry to a group of guys in shorts, t-shirts, and sandals.  I have nothing against that attire – it is what I am wearing as I sit and write this – but a dress code is a good sign that I am walking into a classy place.  I wasn’t suited up, but I was wearing long pants, a collared golf shirt, and with Blundstones on my feet I was welcomed in without any hassle.

It was in fact as I walked past Jimmy and introduced myself that I knew I liked him… He stood like a linebacker and had a face that I suspected could go from teddy bear to grizzly bear in 1.1 seconds.  I know how Jimmy probably feels standing at the portal – I worked the door at a number of establishments in my day.  You show the man respect and he will return it.  If you disrespect it, well don’t expect to enjoy an evening in his bar because you are not going in.  That’s the way it should be… if you aren’t going to respect the doorman, then you are probably not going to respect the barmaids and barmen, and you are probably not going to respect the establishment.  Buh-bye.

Like every bar in Chicago, the Redhead is a non-smoking establishment.  What separates it from most is that if you walk up the short flight of stairs at the back of the joint there is a door that leads to their covered patio which is very comfortably furnished with mostly mis-matching chairs that are far more comfortable than you would expect to find on a patio that is really where smokers go for a few minutes at a time.  Of course, there were cigarette smokers in and out the whole night, every night… but there was also a core of cigar smokers who came out for a cigar… or two… or three, which meant they were there for hours at a shot.  That is the category that I fell into every night… in fact, if you asked me to describe the inside I couldn’t really do it… it was where I walked through to get to my spot.

I wish I remembered the names of the lovely ladies who served me, the gentlemen behind the bar, and the very pleasant and professional manager.  I wish I had sat down to write this article (as I had planned) on the plane home from Chicago in May, but the night before my flight I stayed to close the bar as a series of really nice people bought me drinks (Lagavullin 16 was what I was drinking that week), and I ended up sleeping on the plane.  Life may get in the way sometimes, but when you find a great place and you have a world-renowned blog you want to put them together Winking smile  So here I am, writing about it two months later, because I found Jimmy’s business card in my laptop bag.

By the way, the law in Chicago (yes, I do snicker when I say that) is that you cannot serve alcohol where people smoke.  The Redhead’s answer to this is that they will take your orders on the patio if they know you… but they don’t bring the drinks outside.  They leave them on the counter just inside the door, and you have to go get them.  It’s probably not a perfect system, but it worked great for us (and when I say ‘us’ I mean the people Brian and I went with on Monday… and the people I went with on Tuesday… and the people that Brian and I went with on Wednesday… and the people that Brian and I went with on Thursday… and all of the people we met there and had a hundred great conversations with).

I didn’t spent the week holding court… I did spend the week meeting and chatting with a plethora of great people who came and went.  I recognized some of them from the conference, some were there for other conferences that were in town, some were in town on business, and others actually live in Chicago.  I chatted with people who live as close to me as Rochester (New York), and from as far away as Dublin (Ireland).  We were all there to have a good time, and that is what we did.

I don’t know when I’ll be back in Chicago, but when I am, I know where I’ll be hanging out!


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