American Airlines’ new routes will connect Chicago O’Hare to exciting tropical destinations starting May 5, 2025. Travelers can soon enjoy nonstop flights to St. Croix and San Jose, Costa Rica. These new airline routes in 2025 bring sun-soaked beaches and vibrant cultures within easy reach for Midwest travelers.

Cheap Flights to Mexico and Caribbean Destinations Expand

American Airlines is challenging United’s dominance at O’Hare by boosting service to warm-weather getaways. The airline will increase flights to Caribbean 2025 hotspots, including:

  • Aruba
  • Cancun
  • Curacao
  • Grand Cayman Islands
  • Los Cabos
  • Puerto Vallarta

 

“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,” said Ben Humphrey, American Airlines vice president of Chicago (ORD) operations, in a statement to Travel + Leisure

 

This expansion marks American Airlines’ largest flight increase at any hub in 2025, featuring popular flights to vacation destinations.

Photo by Aaron Hawkins from Getty Images Signature

More Domestic Connections in the Coming Months

The Chicago hub will also see stronger domestic connections. New twice-daily flights from Akron/Canton, Ohio, will begin on October 6. Roanoke, Virginia, will gain additional flights during the holiday travel season.

Bookings open May 5, 2025. Travelers can then access complete schedules and fares. This expansion reflects American Airlines’ commitment to diverse travel options from Chicago. 

For the latest Caribbean travel updates, visit American Airlines’ website.

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*Banner photo by Manuel-V from pixabay