WhiskyFest Chicago — Stories From Our WhiskyFest Adventures

Chicago WhiskyFest is a great time and I have a story or two from this WhiskyFest to share.

James Philip
3 min readMar 4, 2018

Chicago WhiskyFest is an easy one for me since the other half of my company is headquartered in Chicago \ River North. So, no chance of me missing WhiskyFest Chicago!

Before the Chicago Whiskyfest, we may have had a couple of “warm up” drinks before the event but this night was one of those over sampling nights.

** Speaking of samples, I had to “sample” some WhistlePig Boss Hog and Macallan Rare Cask as I write this while listening to Jay-Z (The Blueprint)**

WhistlePig Boss Hog

My Chicago WhiskyFest guests include a pure Texan and a 100% full UK Brit.

We arrive and the place is packed which is a good thing, I like the energy of a full crowd. We get our swag and bottle of water as I think: “this is going to be on the light side of hydration for us.”

The first hour went by really fast for some reason. Then, half way through WhiskyFest Chicago we are all having a great time. At some point, I see the Texan hitting the sushi table like the guy hasn’t eaten in 10 days and the Brit is walking around with 2 drinks (not sure where he got the second glass?) and a full bread roll or something in his mouth but he can’t use his hands to eat, because he has 2 drinks.

WhiskyFest Chicago Sushi Table

As the night goes on, everyone is so lit and the booth attendants are so friendly, the Texan was allegedly pouring his own drinks because he had almost a glass full of whisky. I say allegedly because the night so was so fuzzy. But he was the only one walking around with a WhiskyFest Chicago glass filled to the brim with Whisky.

WhiskyFest Chicago Glenlivet Booth

At some point the Brit keeps saying “oh hell yeah” over and over in that British accent which led to anyone within 10ft of us cracking up.

Want to make friends at an WhiskyFest event? Bring a drunk Brit with you!

The Texan, at the end of the night, decides to start displaying how high he can kick once has “loosened up” from drinking. He may have almost kicked the Brit in the back of the head and that kid is tall!

It was like the Matrix was happening right in front of us, but it was just WhiskyFest. Ever see that ZOOSK commercial where the guy is warming up for darts and says “I am getting stooopid loose?”

Well that was the Texan in the middle of the ballroom…..

The night finishes at Chicago Cut, one of the hottest steak houses in Chicago. At one point the Texan is so drunk, he is talking to the ceramic dog in the restaurants foyer that was wearing a Cubs jersey.

They thought he was high, but it was just a lot of straight whisky.

After a proper steak, a couple more drinks and some truffle scalloped potatoes, we called it a night.

truffle scalloped potatoes

Some how we had a bottle of wine too? I am not sure I recall this!

Are you going to the Chicago WhiskyFest this year? Hit me up on LinkedIn

Check out my article on How To Survive WhiskyFest like a Pro.

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James Philip

Author, Angel Investor and Serial Entrepreneur with over a dozen brands under management. Founder of JMJ Phillip Holdings.