United Airlines Just Made It Easier to Travel to the Cayman Islands This Winter
The Cayman Islands are about to get a lot more accessible this winter.
United Airlines is expanding its nonstop service to Grand Cayman from two major U.S. hubs—Chicago and Washington, D.C.—just in time for the peak travel season.
It’s part of a broader effort by the Cayman Islands Department of Tourism to ramp up airlift from key North American markets, and it comes as demand for the destination continues to surge heading into 2026.
From Washington Dulles, United will operate daily nonstop flights between December 18, 2025, and January 5, 2026, before shifting to a weekly Saturday schedule through the rest of the winter.
From Chicago O’Hare, the carrier will fly five times weekly—on Mondays, Thursdays, Fridays, Saturdays, and Sundays—starting January 1 and running through the end of February.
The added connectivity is a win for travelers looking for a fast, direct route to one of the Caribbean’s most luxurious—and livable—getaways.
Three islands make up the Cayman Islands: Grand Cayman, Cayman Brac, and Little Cayman. Each offers something distinct, from the dive sites off Little Cayman to the dramatic bluff coastlines of Cayman Brac (and its cool blend of laid-back charm and rugged adventure).
But it’s Grand Cayman that typically draws the most visitors, thanks to its famed Seven Mile Beach, legendary culinary scene, and top-level resorts like the Ritz-Carlton, Grand Cayman and the Kimpton Seafire, both of which we’ve stayed at multiple times and adored.
In fact, the Cayman Islands have quietly built a reputation as one of the Caribbean’s top food-focused destinations. There’s a reason it’s one of the Culinary Capitals of the Caribbean, with everything from seaside seafood shacks to internationally acclaimed restaurants lining its shores.
The expansion also reflects a deeper digital strategy. The Cayman Islands were the first Caribbean destination to partner with United’s new Kinective Media platform, launching a campaign in late 2024 designed to reach high-intent travelers through targeted digital channels.
With more flights and more attention than ever, the Cayman Islands are poised for a strong winter—and travelers now have even more ways to get there. And the destination is already off to a strong start so far in 2025, as Caribbean Journal reported.
What about prices? January 2026 United flights from Chicago, for example, are running at about $941 roundtrip.
Caitlin Sullivan began her career with Caribbean Journal as Arts and Culture editor before shifting to travel full time. She writes frequently on the Caribbean cruise industry, flight networks and broader travel news. Her most frequent Caribbean destination? Nassau.
