A buddy is heading to Chicago and asked if I knew of any places to have a civilized cigar. My only experience was outdoors near Lake Michigan. Any suggestions?was
Another possibility, depending on what day(s) of the week your friend will be there:
Cigar Mondays at Vertigo Sky Lounge
Vertigo Sky Lounge
2 W. Erie Street
Chicago, IL 60611
(312) 202-6060
Every Monday from 6-11p
They are not well-equipped - they may sell cigars there (not sure), but they have no cutters or lighters. But it is a great venue with an amazing view and really cool decor.