Starting in early January my work has taken me to Chicago at least every other week. After trying desperately on Twitter to find somewhere to enjoy an after-work smoke while I was there, I turned up empty handed.
On our third trip, my colleague Bob (pictured pouring our scotch) and I asked our hotel concierge if there was any place to enjoy a cigar in the area. After a few conversations with other hotel employees, he returned and told us about Tesa Cigar.
We needed no further convincing so we set off to find a cab, and after a quick stop off to pick up something to drink (it’s BYOB at Tesa) we finally arrived.
Walking through the door, I could feel the weight of the day’s work being lifted off my shoulders. Leather couches and chairs were filled with people doing exactly what we were there to do: unwind over a nice cigar.
The shop owner was extremely helpful while helping us to pick out a medium to full bodied churchill – we found our spot, poured scotch, and settled in. Later in the evening we were joined by two bankers from the Chicago area who we invited to share our couches and our drinks. The atmosphere and the people at Tesa make it feel completely natural to invite strangers to join in on libations and good conversation.
As the crowd thinned out and the clock passed 10pm (their weekday closing time), we began to think that our evening was coming to an end. 
To our pleasant surprise, the store owner grabbed his acoustic guitar, began to casually strum, and invited us to stay a bit longer. We had found heaven, right in the middle of Obamacountry.
Needless to say, if you’re in the Chicago area, definitely take the time to visit Tesa.
Location information and details can be found at their page on CigarPlaces.com.
Their website also contains some more pictures.
You can also follow them on Twitter!
UPDATE
Cigar Jack is holding his 1st Cigar Tweetup at Tesa on March 25th, 2010. Register and get more information on his blog.
