In my never ending quest to piss away my life, the next time I'm in Chicago I'm thinking of visiting the Up Down Cigar Shop on Wells by North Ave, and Iwan Ries on Wabash.

Any local reviews?

http://www.yelp.com/biz/up-down-cigar-shop-chicago
http://www.yelp.com/biz/iwan-ries-and-co-chicago-2

In the late 70's I worked in Old Town. The north end was all "head shops" and hippies, and the south end (where I worked) was all gay bars and transvestite clubs (don't ask)
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Iwan Ries is nice, small smoking area....but they close early. :-)

Up Down is nice as well, and have more accomodating hours.
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