This picture is an Indian Chief wearing his traditional head dress. Head dresses in Red Indian cultures generally represented your status, so for example the Chief in the picture has the largest head dress because he has the highest status.
Pilsen Farmer's Market - just west of Halsted, I think it's on Sundays. A good kickoff point to head down and take in Pilsen. End the run 10 blocks to the west at the National Museum of Mexican Art at 1852 W.