Contour Airlines Expands Service in Caribbean, Chicago

Regional carrier Contour Airlines will begin new service to two destinations next month.

Starting Nov. 1, non-stop service will be available between Chicago (ORD) and Quincy Regional Airport in western Illinois. These short flights, offered daily, allow passengers to then go on to connect to flights offered by Contour Airlines partners such as Alaska Airlines, American Airlines or United Airlines. As usual for the carrier, passengers enjoy free checked bags and complimentary snacks and beverages on its 30-seat aircraft.

Then, Nov. 14, Contour Airlines plans to launch non-stop service between San Juan, Puerto Rico (SJU), and St. Maarten (SXM). Flights will be offered Tuesday, Friday and Sunday.

The new Caribbean route isn’t just a convenient option for island-hopping travelers. According to May-Ling Chun, director of tourism, St. Maarten, it’s also vital for local business.

She said, “We are delighted to see the return of this important air link through our collaboration with Contour Airlines and Princess Juliana International Airport. This route is more than just a connection — it is a bridge that strengthens our economies, deepens cultural ties, and fuels regional tourism. As we continue positioning St. Maarten as a leading Caribbean hub, partnerships like this are essential to achieving sustainable growth, expanding accessibility and creating enriched travel experiences for all.”