Chicagoland! If you’re already dreading the return of freezing temps and lake-effect snow, American Airlines has some good news: new daily nonstop flights from Chicago O’Hare (ORD) to Grand Cayman (GCM) launch this winter, giving Midwest travelers an easy path to paradise.
As part of its expanded winter schedule, American Airlines is adding more service to warm-weather destinations across the Caribbean, Mexico, and Central America. And Grand Cayman—famous for its soft beaches, turquoise waters, and laid-back island lifestyle—is now more accessible than ever from the Windy City.
Why Choose Grand Cayman?
Grand Cayman is a premier destination for winter travel from Chicago. For travelers looking to truly unwind, Rum Point offers the perfect blend of relaxation and adventure. Spend your days sipping cocktails by the beach, paddleboarding over calm Caribbean waters, or sampling island flavors at waterfront restaurants. Families and couples alike will love the slower pace and natural beauty of the island’s North Side.
This new daily flight makes it easier than ever for Chicagoans to swap ice scrapers for island cocktails—with no long layovers or complicated connections. The nonstop route—AA 998—departs ORD at 8:10 am and lands in Grand Cayman at 12:56 pm, putting you on island time in less than four hours.
When Does the New Service Begin?
The daily service begins December 18, 2025, just in time for holiday escapes, New Year’s vacations, and anyone looking to avoid January’s deep freeze. Tickets are available for purchase now on AA.com or via the American Airlines app. The direct service will run through the end of April 2026.
Travel Tip: With unpredictable Chicago winter weather, travel insurance is a smart investment. It can protect your trip in the event of delays, cancellations, or illness. We recommend Rental Guardian policies, which cover your entire group and include 24/7 assistance. For complete peace of mind, consider their Cancel-For-Any-Reason (CFAR) option.
Don’t wait—winter will be here before you know it! Book your direct flight from Chicago to Grand Cayman and get ready to enjoy barefoot luxury at Rum Point Resort.
Source: American Airlines Newsroom
