Americans Can Now Fly Nonstop From The Midwest To This Sunny Caribbean Island

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Already feel the winter blues settling in with the gray skies, temperatures in the low 20s, and lack of sunlight? The Midwest and its grand lakes and lush nature may well be stunning in summer, but if you live anywhere near the Chicago Metropolitan Area, you know January hits like a brick.

Thankfully there’s always a 4 to 5-hour flight down to the sun-drenched Tropics to save us from freezing our bottoms off: Cancun, Punta Cana, MoBay and so on.

The capitals of all-inclusive and week-round pampering, but hey, maybe this time ’round, after spending the last 3 or 4 winters south of the border, you’re craving something a little… different. Well, your prayers have been answered:

This year, American Airliens is launching new direct flights from Chicago O’Hare to Curaçao, a sunny island in the Dutch Caribbean best known for its colorful capital, white-sand beaches, and impressive safety levels:

Fly From Chicago To One Of The Most Beautiful Island Getaways In The Caribbean

Since December 5, 2025, American Airlines has been operating their direct flights from Chicago O’Hare (ORD) to Curaçao International Airport (CUR), which serves the Dutch Caribbean island of Curaçao.

Departures are scheduled for 8 AM once a week, every Saturday, up to April 4, 2026. The total flight time is around 5 hours, and the route opens up an entire new world of possibilities for Mdiwest travelers getting to this underrated side of the Caribbean.

If you’ve never been to this of the Caribbean before, you might be in for a bit of a surprise. For starters, Curaçao is a nation within the Kingdom of the Netherlands, and though it is considered a nation, it’s not exactly a sovereign country.

Its citizens hold Dutch passports, the local governance is Dutch-overseen, and needless to say, Spanish isn’t the lingua franca here: Dutch and Papiamentu (a Portuguese croele language) are the official means of communication, and English is also widely spoken.

Why Visit Curaçao This Winter

That’s one of the many reasons why Curaçao makes for such a fascinating getaway:

Yes, it is irrevocably Dutch, as its own capital town Willemstad would attest, be it the name, of the unusually-colorful Amsterdam-style buildings and canals—but then again, it’s not stroopwafels and soused hering you’ll find sold in markets here, but fresh fruit, cornmeal takeouts, and flavorful seafood.

In a way, it’s the perfect mix of European and Caribbean cultures, and compared to its island counterparts, it’s a lot more laid-back and peaceful in comparison.

Be it on the candy-colored streets of Willemstad, or one of the many white-sand Playas hugged by teal-colored seas, from Kenepa down to Porto Mari, tourists have very few, if anything to worry about on the security front:

It’s A Remarkably Safe Destination

According to the U.S. Department of State, which classes Curaçao as a Level 1 destination, it is very safe, and unlike a majority of Caribbean islands, the robust security doesn’t apply exclusively to resort zones.

Think of Cancun: yes, it’s pretty safe, but only if you’re restricting your movement to the touristy Hotel Zone. We wouldn’t be exactly keen on venturing farther away, into less-developed, suburban areas of the city where gangs typically operate.

Curaçao benefits both from being under the supervision of the Netherlands, a European state known for its low levels of corruption and tolerance to organized crime, and its small size: with a single major settlement, and at only 171 square miles, it’s far easier to patrol.

In general, the biggest threat to tourists in Curaçao is getting pickpocketed, or being victims of other forms of petty theft. That said, these happen seldomly, and are by no means a common occurence across the island, within or outside resort grounds.

What Makes Curaçao Stand Out

Flying with American Airlines to Curaçao and back, you’ll have a whole week on the island to beach-hop and discover its colonial gems.

If you’re wondering how much Saturday-to-Saturday reservations are this winter, they range from only $425 for an apartment for 2 guests, privately-managed, to a much-more expensive $4,074 at five-star, all-inclusive resorts like the Mangrove Beach Corandon Curacao.

There’s something in Curaçao for every type of traveler and budget, and that’s part of the reason why it’s such an appealing Caribbean escapade.

Here’s a summary of all the things that makes Curaçao a great, hassle-free vacay for Midwesterners:

• It’s got beautiful Dutch-inspired architecture
• The beaches are clean and safe to visit
• Security levels on the island are high
• It’s now a short 5-hour flight away

Before we go, we should probably tell you roundtrip fares average only $557 on Google Flights. As if you needed any more incentives.