I have been fortunate enough to attend some really great whiskey, particularly bourbon related events in the past.  I’ve been to two Pappy For Your Pappy tasting dinners with the Van Winkle family at Buffalo Trace, two Bourbon Classics in Louisville, and the The Great Kentucky Bourbon Tasting & Gala™at the Kentucky Bourbon Festival, among other great events.  But, as a Christmas gift from my wife, this was the year we went for the granddaddy of them all – WhiskyFest in Chicago.

WhiskyFest is sponsored by the Whisky Advocate magazine, and boasts a staggering number of brands and makes.  Because it includes not only Bourbon and Rye but also Scotch, Irish, Japanese, Flavored and Tennessee (as well as a few beers, wines, gins and rums), it has a far wider range than those Bourbon only events.  This year there were 133 Brands, with 355 individual bottlings.

But that is all for part two.

One of the great things about WhiskyFest is the large number of whiskey-related events that take place all over Chicago the week of.  There are tastings, ‘Meet the Distiller’ events, brand unveilings and many others.  We decided to head to Chicago a day early and take in one of the events – the 4th Annual Whiskey Affair at Untitled.  We were not disappointed.

Untitled is a “Supper Club” in Chicago’s Near North Side with the “speakeasy” vibe that is very much in trend these days.  Their website encourages a rather formal dress code (no jeans, no athletic shoes), but that was no problem.  Upon entering and going down the main staircase (underneath a particularly impressive liquor collection), we checked in with our pre-purchased tickets.  The event was $50 each – certainly not a bad price – and we were there before the tasting opened, so we took in the sights and sounds of the rather expansive place.  The lighting was dim and there was music overhead, but most notable were the intimate booths and benches around.  It has a very cool atmosphere – but this is a bourbon blog, not a Yelp review, so I will move on.

When we checked in, we were given Glencairn glasses, a lanyard and (I believe) 20 tickets.  The instructions were given as well – each ticket is for a tasting, hand it to the pourer upon your sample.  At 7:00 the doors to several more rooms opened, and we headed in.

The list of whiskies at the Whiskey Affair was impressive.  The major players were there with nicely set up booths – Maker’s Mark, Jim Beam, Wild Turkey, Bulleit, Jack Daniels and so on – but there were also many whiskey makers not represented at WhiskyFest proper the next night like Journeyman, Belle Meade and Dad’s Hat.  Smooth Ambler was there, although not at WhiskyFest, and offered tastes of their new Contradiction (a blend of wheat and rye bourbons) which proved very interesting and enjoyable.

We moved from booth to booth, trying new items and old favorites.  To be honest, the only booth requiring us to drop in our tickets was Maker’s Mark, who were offering pours of their regular, 46 and Cask Strength bourbons.  The rest were happy to pour away, and talk about their product.

We spent several hours moving around and talking to brand reps while weaving in and out of the diverse and often very well-dressed crowd (there were more women drinking whiskey at the much much smaller Whiskey Affair than the entire WhiskyFest the next night).  The drinks were almost exclusively bourbon and rye – there were a few scotches and irish whiskeys, but they were in the minority – and when the event ended, there were a few that had peaked my interest, namely:

• WhistlePig Old World, a 12 year rye that has been finished in assorted wine casks, giving it a nice smooth roundness
• Smooth Ambler Contradiction, the aforementioned wheat and rye blend, that had both opening sweetness and a peppery finish
• Jack Daniels Single Barrel, Barrel Proof, yes, JD has put out a barrel proof and I thought it was fantastic

When the Whiskey Affair ended, Untitled had an aerialist/burlesque show that we probably would have stuck around and enjoyed thoroughly.  But after sampling a couple dozen whiskies, and with the big event the next day, we headed back to the hotel to recharge our batteries for WhiskyFest itself.  Kudo’s to Untitled, they threw a fantastic event, and I am very much looking forward to stopping in for dinner when I am in Chicago next!

…and that will come in part two!