Up Down Cigar
Maybe because of Chicago No Smoking law, smoking indoors, in a such cozy-talk-free-atmosphere cigar shop made the experience such a great one.
It is true in Chicago (and all USA) they don’t sell Cuban cigar but there are many great Nicaraguan and Dominican cigar you can smoke. “Up Down Cigar” definitely have the largest cigar selection with really hands-on experienced staff in Chicago.
If you’re ever a cigar smoker and happens to be in Chicago you should pass by.