At 29, Hepburn had already won an Oscar as Best Actress. She was in town appearing in a stage version of “Jane Eyre.” Hughes was a dashing 30-year-old oil millionaire who had become a Hollywood producer. He was also a famous aviator. 

 

On January 19, Hughes broke his own speed record by flying from Los Angeles to New York in 7 hours, 28 minutes. Then he flew to Chicago and checked into Hepburn’s hotel. He got a separate room, three floors away. That’s the way things were done in 1937. 

 

The wedding rumors started immediately. County Clerk Michael Flynn helped the story by announcing he was ready to personally issue a marriage license to Katie and Howard. When the County Building opened for business on January 21, a crowd had already gathered, hoping to catch a glimpse of the happy couple. 

 

By mid-day, over 3,000 people clogged the corridors. Many in the throng were County employees who had abandoned their offices to join the stake-out. The few couples who came for their own marriage licenses had trouble getting through the mob. 

 

Closing time arrived. Hepburn and Hughes still hadn’t shown up. Now attention shifted to the Ambassador East, where photographers and hundreds more fans kept vigil. Hepburn finally emerged and left for the theater, without Hughes. The paparazzi followed.

 

After the performance, Hepburn tried to avoid her pursuers with a decoy–she dressed her maid in a mink jacket and slacks, and sent the woman off in a cab. The trick didn’t work. When the actress did leave, the press was still on her tail. 

 

Hepburn returned to the hotel at 3 a.m., accompanied by her co-star. When one waiting photographer snapped a picture, the escort stepped forward and smashed the camera. Meanwhile, Hughes remained out of sight. 

 

Katharine Hepburn and Howard Hughes never did get married, in Chicago or anyplace else. They eventually went their separate ways. Hughes became a billionaire and died an eccentric recluse in 1976. Hepburn won three more Oscars and lived to be 96. 

 

As a post-script, Cate Blanchett later won an Academy Award for portraying Hepburn in the Howard Hughes biography film, The Aviator. Does that count as a fifth Oscar for Katie H?