Chicagoland! If you’re already dreading the return of freezing temps and lake-effect snow, American Airlines has some good news: new daily service from Chicago O’Hare (ORD) to Grand Cayman (GCM) launches this winter, giving Midwest residents an easy path to paradise.
As part of its expanded winter schedule, American Airlines is significantly increasing flights to warm-weather destinations across the Caribbean, Mexico, and Central America. And Grand Cayman — known for its white-sand beaches, crystal-clear waters, and laid-back island vibes — is now more accessible than ever from the Windy City.
Why Grand Cayman?
Grand Cayman is a top-tier destination for winter travel from Chicago. Whether you’re snorkeling with stingrays, relaxing on Seven Mile Beach, or exploring the island’s delectable foodie scene, the Cayman Islands offer a warm and welcoming escape from Midwest winters.
This new daily flight makes it easier than ever for Chicagoans to trade ice scrapers for island cocktails—with no long layovers or complicated connections. The new direct flight—AA 998—takes off from ORD at 8:10 am and lands in Grand Cayman at 12:56 pm, putting you on island time in less than 4 hours.
When Does the New Service Begin?
The increase to daily service begins December 18, 2025, just in time for holiday getaways, New Year vacations, and those looking to escape January’s deep freeze. Tickets for daily winter flights are available for purchase online, or via the American Airline app. The new 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 dream vacation in the event of flight delays, cancellations, or illness. Check out the policies we offer from Rental Guardian that cover all members of your group and offer 24/7 travel assistance. There’s even a Cancel-For-Any-Reason (CFAR) policy for complete peace of mind.
Don’t wait — winter will be here before you know it! Book your direct flight from Chicago to Grand Cayman and get ready to thaw out under the island sun.
Source: American Airlines
