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American Adds 7 New Routes From Chicago, Increases Flights To Winter Sun Destinations

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Daniel Ross
Edited by: Keri Stooksbury
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Summer might only be on the horizon, but American Airlines wants to give Chicagoans more options to escape the cold this coming winter.

The airline has released an update announcing 7 new routes from its hub at Chicago O’Hare (ORD) and an increase in the number of services to popular winter sun destinations.

Of the 7 new routes, 5 will be to new international vacation spots in the Caribbean and Central America.

“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, vice president of American’s operations at Chicago O’Hare (ORD).

Here are the details.

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American Airlines’ 7 New Routes Schedule From Chicago

American wants to be the Chicagoan’s airline of choice this winter, despite United’s best efforts.

Of American’s 5 new international routes from Chicago (ORD), United already operates service to Guatemala City, Guatamala (GUA), San José, Costa Rica (SJO), and Sint Maarten (SXM). However, American will be the only airline to operate services from Chicago to Curaçao (CUR) and St. Thomas, U.S. Virgin Islands (STX).

Map of new international American Airlines routes from Chicago ORD
Map of American Airlines’ new international routes from Chicago O’Hare starting this winter. Image Credit: Great Circle Mapper

American’s new domestic routes to Akron/Canton, Ohio (CAK) and Roanoke, Virginia (ROA) will also compete against United.

The table below provides more details, including each route’s start dates and frequencies:

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New Destination

Start Date

Frequency

Akron/Canon, Ohio (CAK)

October 6

2x daily

Curaçao (CUR)

December 6

Saturdays only

Guatemala City, Guatamala (GUA)

November 6

Up to 3x weekly

Roanoke, Virginia (ROA)

August 6

Daily

San José, Costa Rica (SJO)

November 2

Daily

Sint Maarten (SXM)

November 8

Saturdays only

St. Croix, U.S. Virgin Islands (STX)

December 8

Saturdays only

Tickets for the new routes will go on sale starting May 5.

Hot Tip:

Cash fares to winter sun destinations like these can be very expensive. That’s why we like to earn as many American Airlines AAdvantage miles as possible so we can use points instead.

American Adds More Flights to These Winter Sun Destinations

As part of this winter season route expansion, American will increase the number of flights it operates to 10 popular vacation destinations.

The focus is the Caribbean, Central America, and Mexico, with flights increasing to at least daily on all routes. The carrier will operate up to 3x daily to Cancun, Mexico (CUN)!

The destinations with increased services, as well as their start date and frequency, are detailed below:

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Destination With Increased Services

Start Date

New Frequency

Aruba (AUA)

December 18

Daily

Cancun, Mexico (CUN)

November 2

Up to 3x daily

Grand Cayman, Cayman Islands (GCM)

December 18

Daily

Liberia, Costa Rica (LIR)

December 18

Daily

Los Cabos, Mexico (SJD)

November 2

Up to 2x daily

Montego Bay, Jamaica (MBJ)

November 2

Up to 2x daily

Nassau, Bahamas (NAS)

December 18

Up to daily

Puerto Vallarta, Mexico (PVR)

December 18 to January 6, 2026

2x daily

San Juan, Puerto Rico (SJU)

December 18

Up to 2x daily

St. Thomas (STT)

December 18

Up to daily

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Final Thoughts

If there were an airline popularity contest at Chicago O’Hare, American would be vying for the number 1 spot with this expanded winter sun schedule.

The increased frequencies and new routes, especially to the currently unserved destinations of Curaçao and St. Thomas, will likely come in very handy when Chicagoans are planning their winter getaways.

Daniel Ross's image

About Daniel Ross

Daniel has loved aviation and travel his entire life. He earned a Master of Science in Air Transport Management and has written about travel and aviation in publications like Simple Flying, The Points Guy, and more.

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