Yes, the movie "Medium Cool", a 1969 release had events that took place in Chicago. The artists associated with the movie include Robert Foster, Verna Bloom, Peter Bonrez, Marianna Hill etc besides various others.

The character portrayed by Verna bloom had moved to the city of Chicago from West Virginia. The last scenes of the movie are based at Chicago and feature the 'Democratic National Convention' that takes place during the 1968 summer.

A boy is missing and his mother is in search of him and is looking for help. She tries to get help from another character in the movie, Casselis but he is completely involved in filming the Chicago convention.

http://en.wikipedia.org/wiki/Medium_Cool

http://www.imdb.com/title/tt0064652/

If you are single in Chicago, IL and not tried any dating sites then try a totally free dating site in Chicago, IL.

http://www.datehookup.com/Singles-IL-Chicago.htm

Paid dating sites are boring. This website mentioned above is a lot more fun and have singles chat, forums, and groups for all types of friends, interests and a lot more.

There are some other singles dating sites where they will review your profile and evaluate who might be a good match for you.

http://www.chicagosingles.org/