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New York, NY
USA

We are parents, too. We think traveling well and traveling with children shouldn’t be mutually exclusive. We have limited vacation time, and we’re not spending our few days of freedom in lousy hotels eating bad food. We know the world is full of wonderful resorts, cool urban escapes and far-flung lodges that can make our time with our kids count. We want it all, and we don’t think it should be so hard to find. So we’re going to share it with you.

 

Direct Flights to the Caribbean - Chicago

Travel Journal

Travel Journal

Dispatches from around the world

Direct Flights to the Caribbean - Chicago

Henley Vazquez

Last winter was cold for everyone, but it was particularly rough on Chicago residents, who logged an unprecedented number of subzero days and twice the average amount of snow. This winter might be as bad. Here’s your guide on how to get away easily, and where to stay. Pack up those baby cubs and head south.  Coming from the East Coast? Check out your options here.


 
 

Bahamas

There’s life beyond Atlantis. One & Only’s sophisticated Ocean Club sits a short drive down the beach from the kid-adored behemoth, so mom and dad can have the resort they love (with a great kids’ club) but still do a day or two at the water park. A new upscale complex will be opening later this winter as well.
Where to Stay: One & Only Ocean Club plus Rosewood, SLS and Grand Hyatt to come when the new Baha Mar complex opens.


 
 

Cancun/Riviera Maya

This stretch of coast, known as the Riviera Maya, reaches from the crowded Cancun hotel zone to the boho-chic beach shacks in Tulum. There’s something for everyone, and great culture, food and eco-adventure that give this destination more umph than the average fly-and-flop vacation. An extra perk is that West and East Coasters also have direct flights, making this beachy paradise ideal for bicoastal friends and family looking for a meeting spot.
Where to Stay: Rosewood MayakobaFairmont MayakobaBanyan Tree MayakobaNizucBelmond Maroma and Esencia; in Tulum, Las Ranitas and La Zebra


 
 

Dominican Republic

With frequent flights from cities around the country, the DR is quickly becoming a rival for Puerto Rico when it comes to competitive pricing. All the better, since Chicagoans can access some pretty sweet resorts that are worth a splurge. Punta Cana has the longer but busier beach, while La Romana has the calmer waters.
Where to Stay: Tortuga Bay in Punta Cana; Casa del Campo in La Romana


 
 

Grand Cayman

It’s not just for offshore banking. The famous Seven Mile Beach is postcard-perfect sandcastle territory, and more adventurous families can head to Stingray City, a North Sound sandbar where the kids get an up-close look at these massive aquatic creatures. The dining scene is stellar as well, with restaurants from New York’s Michelin-starred chef Eric Ripert and Miami’s star Michael Schwartz.
Where to Stay: Ritz-Carlton Grand Cayman


 
 

Jamaica

Reggae, rainforest, rum...and plenty for the kids, too. While Jamaica tends to be more a resort-focused destination than some of our other favorites, the island has hotels that families never need, or want, to leave. Montego Bay’s airport is a short drive from Round Hill, an upscale classic, and Half Moon Bay, with its British sensibilities, while the uber hip GoldenEye requires an hour’s drive.
Where to Stay: Round Hill, Half Moon Bay, GoldenEye


 
 

Puerto Rico

San Juan has the busiest airport in the Caribbean, and more flights mean lower prices. While some families use San Juan as the gateway to other islands, Puerto Rico now has top-notch resorts that rival the region’s best. There’s also great colonial architecture in old San Juan and the amazing El Yunque rainforest to explore. The clincher? You’ll clear customs in San Juan, meaning no immigration when you land at home, and you don’t need a passport.
Where to Stay: Dorado BeachSt. Regis Bahia BeachEl Conquistador


 
 

US Virgin Islands

As with St. Martin and Anguilla, St. John is less crowded (two-thirds of the island is a national park) but you’ll take a boat from St. Thomas, where flights land, to get there. And St. John’s Cruz Bay might be one of our favorite Caribbean towns, full of laidback eateries perfect for families. Bonus: the US Virgin Islands don’t require a passport to visit, and passengers won’t wait for immigration when arriving home.
Where to Stay: Ritz-Carlton on St. Thomas, Caneel Bay on St. John


While Chicagoans lack some of the Caribbean connections East Coasters can access, O’Hare earns bonus points for better routes to the Pacific Coast. Look for direct connections into Puerto Vallarta, Los Cabos and Liberia, Costa Rica, all F+F favorites. If you’re headed there and need some tips on where to stay, drop us a line.