According to Jiangsu Public News,

a woman identified as Li reportedly bought plane tickets and flight-delay insurance using different identity information and was taken into criminal detention by Nanjing police on suspicion of insurance fraud and fraud. Police said Li claimed to have previously worked in aviation services, and was familiar with both flight-delay information and the insurance claims process. She would select routes with a high likelihood of delay, checking before booking whether the itinerary had any extreme-weather risks. A typical insurance premium was about 40 yuan, while insurance payouts for delays ranged from 400 to 2,000 yuan. For longer delays, the payout could reach 7,000 to 8,000 yuan. If she learned a flight was unlikely to be delayed, Li would cancel the ticket before departure to minimize losses. A preliminary count shows that from 2015 to now she bought tickets on 900 flights that were delayed, and received nearly 3 million yuan in claim payouts.

In the U.S., on-time performance for flights is much higher than in China, so this kind of tactic is much less likely to work here. Still, many U.S. credit cards offer flight-delay insurance, and I’ve heard of people using delay coverage to get reimbursed for certain airport “spending” after a delay. If it’s a small amount, it may be manageable; if the scale gets large, it’s worth thinking carefully.