United Air Lines (United) is significantly expanding its nonstop service to the Cayman Islands for the peak winter 2025/2026 season, a key development in the Cayman Islands Department of Tourism's (CIDOT) strategic aviation growth initiative aimed at increasing airlift from high-value markets.
The expanded service from Chicago O'Hare (ORD) and Washington Dulles International Airport (IAD) represents the successful execution of CIDOT's comprehensive aviation strategy, which focuses on cultivating strong airline partnerships to meet growing demand for the destination.
IAD Winter Schedule
ORD Winter Schedule
"This expansion of United's service from Chicago and Washington D.C. directly aligns with our aviation strategy of securing increased airlift from key markets with high-value travellers," shared Director of Tourism, Rosa Harris. "Our data-driven approach to route development continues to yield results, positioning the Cayman Islands for sustained growth in our core markets. We punch above our weight class and engage in pioneering partnerships to deliver on our mandate for new business opportunities for the Cayman Islands tourism industry "
The aviation strategy has been further supported by CIDOT's pioneering investment in United's Kinective Media platform, making the Cayman Islands the first Caribbean destination to launch an omnichannel campaign on this innovative platform in late 2024.
"Our aviation strategy combines targeted route development with cutting-edge marketing initiatives to drive demand," said Gary Hendricks-Dominguez, Deputy Director of International Marketing and Promotions. "Our investment in United's Kinective Media platform is a perfect example of how we're leveraging innovative channels to reach high-value travelers in these markets. The remarkable demand we're already seeing for winter 2026 demonstrates the effectiveness of our rigorous and competitive approach."
The Cayman Islands has already emerged as a strong performer for winter 2026. This robust demand underscores the Cayman Islands' position as the premier Caribbean destination, offering travellers a unique three-island experience across Grand Cayman, Cayman Brac, and Little Cayman. Known as the Culinary Capital of the Caribbean, visitors can indulge in exceptional dining experiences ranging from fine restaurants to local seafood shacks. Beyond the world-class cuisine, winter travellers will enjoy pristine beaches, crystal-clear waters, world-renowned diving, and perfect temperatures averaging 78-85°F throughout the winter season, making the Cayman Islands the ultimate winter escape that combines luxury, natural beauty, and unparalleled hospitality.
Flights from ORD and IAD are available to book at united.com. To start planning your trip, visit www.visitcaymanislands.com.