While a large part of the U.S. is only now starting to feel the first wave of warm weather, the airline industry is already looking ahead at the period during which many turn to them to escape the winter cold.
At the start of April, American Airlines (AAL) rounded out its Mexico network to 30 destinations with a new route to Puerto Escondido on the Oaxacan Coast, alongside a new flight between Chicago and Honolulu announced at the end of winter.
Budget carriers like Spirit Airlines (SAVE) and Frontier (FRON) have meanwhile honed in on destinations such as Costa Rica, Puerto Rico, and the Dominican Republic with new routes for its 2025-2026 winter season — the demand is coming both from sun-seekers and members of the diaspora flying to and from the United States.
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American Airlines is promising flyers ‘a reprieve from the bitter Midwest winter’
On April 30, American Airlines is announcing seven routes and five new destinations in the tropics. New flights to the Dutch territories of Curaçao and St. Maarten, St. Croix in the U.S. Virgin Islands, Guatemala City, and Puerto Rico’s San Jose will all start running from Chicago’s O’Hare International Airport (ORD) throughout November and December 2025.
Domestically, the carrier is also launching new flights from Chicago to Virginia’s Roanoke-Blacksburg Regional Airport (ROA) and Ohio’s Akron-Canton Airport (CAK) — all in effort to build out its Chicago hub alongside its main base in Dallas.
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“As we get our first taste of spring in Chicago, we are already looking ahead to giving our customers a reprieve from the bitter Midwest winter with more than double the flights to popular vacation spots,” American Airlines Vice President of ORD Operations Ben Humphrey said in a statement. “Building on our major Chicago expansion, we continue to strengthen our network and reaffirm our commitment to the Chicago communities we serve — our loyal customers, the local economy, and our team members who are the driving force behind our operation.”
A view of Charlotte Amalie Harbor in St. Thomas of the U.S. Virgin Islands.
Image source: Pixabay
Looking to test those new Caribbean flights? Some start dates to keep in mind
Chicago was chosen both due to the high number of sun-seekers looking to get away in the winter and its geographic location for transferring from other parts of the U.S. For the upcoming winter season, American will also be upping to daily service for other tropical destinations like St. Thomas, Grand Cayman, Aruba, and Liberia in Costa Rica. Service was only once a week for some of these destinations last year.
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The domestic routes will start running earlier than the tropical ones — Aug. 6 for Chicago-Roanoke and Oct. 6 for Chicago-Akron — while the flight to Costa Rica’s San Jose will begin on Nov. 2.
Chicago-Guatemala City will run three times a week starting Nov. 6, while the St. Maarten flight will start Nov. 8 and run once a week on Saturdays. Service to Curaçao and St. Croix will begin on Dec. 6 and also run once per week throughout the season.
The new flights will be available for booking on the American Airlines website starting May 5.
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