Windy City is a 1984 American dramatic film written and directed by Armyan Bernstein and starring John Shea, Kate Capshaw, and Josh Mostel.
Danny Morgan, a writer living in Chicago, feels his world crashing down around him. His former girlfriend, Emily, is about to get married. His close childhood friend, Sol, has leukemia. Danny reflects on his past relationship with Emily while also trying to give Sol the send-off he deserves by pitching the idea of a sailing trip to their group of friends, due to their childhood fantasies of being adventurers and pirates, even though he finds opposition from his friends on the grounds that they have obligations and they are unable to just take off.
This was the sixth film released by the short lived CBS Theatrical Films, the film production branch of the television network of the same name. The following year, the production company closed its doors, and the film has never been released on DVD.
This film features examples of:
- Bittersweet Ending: Danny is ultimately unable to convince Emily to take him back and to stop her wedding, and Sol ultimately dies from his leukemia. However, Danny is ultimately able to give Sol his sailing trip just days before his death, and the ending reveals that Emily later got divorced and hints at a possible reconciliation with Danny.
- Growing Up Sucks: Averted Trope with most of the Rogues who grew up to have happy families and successful careers. Played straight with Danny and Sol who can't get over the fact their lives didn't turn out like the movies.
- Last Request: A big part of the film focuses on Danny trying to give his friend Sol, who has leukemia, the send-off he deserves by giving him a sailing trip with their group of friends, who had childhood fantasies of being adventurers and pirates.
- Maybe Ever After: At the end, it's shown that years after she married, Emily is now divorced, and she and Danny hint at a possible reconciliation.
- No Romantic Resolution: Danny's paralel storyline to wanting to give Sol his sailing trip is to try to win back the heart of his former girlfriend Emily, who is about to get married. While he is shown to ultimately be unsuccessful in the latter, the ending hints at a possible reconciliation between them.
- Wedding Deadline: Danny tries to beat this by reaching Emily's wedding. He fails.
