Headed to Chicago tomorrow

[vinyl.rs]

UpDown is amazing spot, and Phil (the guy who runs it nowdays) is great man! Depending on your stay as folks above said, Iwan Ries or Jack Shwartz would be the move, alongside Biggs. Suburbs, Casa De Montecristo (southwest) or Byron Cigar Lounge (northwest) are great spots (overpriced tho)

[Dmex]

I ended up not having as much time as I was hoping I would and so I wanted to try a new place.  I probably should have gone to UpDown lol but instead I opted for Biggs.  It was closer to me and I had wanted to check it out last time I was in Chicago. 

I arrived and the place looked great from the outside.  Big beautiful mansion type location and they have lots of outside seating where you can smoke.  We went inside and walked through their humidor and looked around the cabinets.... the selection is just ok.  Nothing stands out that I could see, but I picked up a few sticks and talked to the guy at the register.  He informed my that smoking upstairs was members only or that I could buy a day pass for 100/pp.  That seemed a bit steep to me considering I was only there for one smoke and there was two of us, so we opted to light up in their small but comfy lounge area inside near the register.  About half way through my cigar I talked to the guy again and gifted him a JL2, I explained that I was here from out of town and was curious to take a look upstairs, he was totally cool about it and let us go upstairs to look around.  Beautiful place to smoke, lots of rooms for small and large parties.  He said the cost was about 3500 year.  We went up to the third floor and looked around a bit more and came back down and finished our cigars out on the courtyard.  The guy offered to extend us a day pass at a much more reasonable price but by that point the afternoon was closing on us and I needed to get back to the wife. It was a good experience.  Maybe another time when I have more days to visit I'll return.  Chicago is a great town.