The Dilemma Filming Locations
The Dilemma was filmed in Chicago in the United States of America.
United Center as Hockey Arena
Blackhawk hockey scenes.
Smith & Wollensky
The waterfront dining on the Chicago River in the opening scene takes place at Smith & Wollensky's
Green Mill Cocktail Lounge
The scene where Nick dances on their double date was filmed at Green Mill.
Garfield Park Conservatory
The scene where Ronny looks into proposing at the botanical gardens but finds Nick's wife with another man is filmed at the Garfield Park Conservatory..