6 Caribbean Destinations under $465 Round Trip from Chicago This Winter

See the 6 cheapest Caribbean islands for a winter getaway from Chicago this year, each of which can be reached for less than $465.

Dakota Smith - Jan. 27, 2015

It's never too early to start planning one's escape from the cold, windy Chicago winters. So how about a nice jaunt down to the Caribbean where the seas are warm and only the drinks are cold? Check out six Caribbean islands that can be reached for under $465 round trip from Chicago this winter. These deals are so cheap you'd be crazy to not at least daydream about a winter getaway!

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6. Fly from Chicago to Grand Cayman, Cayman Islands, for $465 round trip

Fares from Chicago to the Cayman Islands are pretty affordable, making the jaunt through the pearly Caribbean sands and sleepy towns of this British Overseas Territory a tempting possibility for many a Chicagoan this fall. The flight takes just under four hours non-stop and drops passengers in the capital at George Town — the perfect base from which to explore the paradisaical outer islands of Brac and Little Cayman.

Top three reasons to visit Grand Cayman:

  • The Seven Mile Beach: Quite simply one of the most beautiful beaches in the world.

  • The luxuries: Grand Cayman has every kind of hotel you could want, from deluxe all-inclusive resorts towering over the shoreline to intimate B&Bs. And its dining scene is world-class, too, with a string of sublime seafood restaurants looking out over the Caribbean Sea.

  • The other islands: If Grand Cayman is all glitz and luxury, then its two neighbors provide an escape from it all into a wild and beautiful natural world, with terrific birdwatching, hiking, snorkeling and diving.

Flight is 4 hours direct on Cayman Airways

Examples of itineraries from Chicago to Cayman Islands recently found:
- $438 round trip on US Airways from Dec 7 to Dec 18
- $439 round trip on American from Dec 31 to Jan 11
- $552 round trip on Cayman Airways from Dec 31 to Jan 11
- Search for flights on your dates


5. Fly from Chicago to Punta Cana, Dominican Republic, for $435 round trip

This gateway to the Dominican Republic is perhaps also its most important, precisely because it's one of the kingpins of all-inclusive holidaying in the whole Caribbean: the island’s eastern region of Punta Cana. So, if it’s butler service, spa facilities and swim-up bars you’re after then why not consider a non-stop flight to Punta Cana in just over four hours.

Top three reasons to visit Punta Cana:

  • The sun, sea and sand: Somehow, despite decades of unrestrained development, this stretch of Dominican shoreline has remained a Caribbean jewel of white sand, warm sea, swaying palms, beach bars and ramshackle seafood eateries.
  • The golf: Several of the region's most exquisite golf courses snake alongside the blue waters near Punta Cana, including the truly sublime Punta Espada Golf Course, frequently voted the best in the Carribean.
  • The nightlife: Cocktails on the beach by day, shots in wildly eccentric clubs by night - it'll be tempting to spend your whole time in Punta Cana sozzled.

Flight is 4 hours and 35 minutes direct on United

Examples of itineraries from Chicago to Punta Cana recently found:
- $435 round trip on US Airways from Feb 16 to Feb 19
- $486 round trip on United from Dec 31 to Jan 11
- $439 round trip on US Airways from Jan 13 to Jan 24
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4. Fly from Chicago to Saint Thomas, US Virgin Islands, for $405 round trip

Travelers from Chicago won’t even need to pack their passport for this flight out of the city’s O'Hare Airport. Either direct with United or with a connection on US Airways, passengers will arrive amid the jungle-clad hills and emerald waters of Saint Thomas Island, the veritable gateway to the United States Virgin Islands. From here they’ll be free to explore the archipelago, dipping in and out of the warm autumn shore currents, sunning themselves on the sands and sampling the fiery concoctions of the islands’ Carib-American-style kitchen.

Flight is 5 hours direct on United

Examples of itineraries from Chicago to Saint Thomas recently found:
- $418 round trip on JetBlue from Jan 18 to Jan 29
- $475 round trip on United from Jan 18 to Jan 29
- $411 round trip on US Airways from Jan 2 to Jan 13
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3. Fly from Chicago to Nassau, Bahamas, for $374 round trip

Crazy, culturally-mind-boggling Nassau was once the stomping ground of Blackbeard and co.; a pirate free state of lawless buccaneers and pistol waving sailors who wanted nothing but a good time. Fast forward to today and not that much has changed, except perhaps there’s now some super good deals on flights from O'Hare to the city’s Lynden Pindling International Airport, bringing Chicagoans into the lively Caribbean fold for as little as $343 return! That isn’t even enough travel time to develop scurvy.

Top three reasons to visit Nassau:

  • The lively downtown: Walk from pastel-pink government buildings to strings of duty-free shops hawking rum cakes and booze, then dive into the banging bar and club scene once the sun has set.
  • The wild history: The wild history of lawless pirates and lawful exploitation is told at a variety of attractions, such as the Pompey Museum, which charts slaves' journeys from Africa to the Caribbean, as well as the more fun and facetious Pirates of Nassau Museum.
  • The diving and snorkeling: Nassau is choc-full of friendly and laid-back dive operators offering PADI courses and organised trips out into the coral-filled waters surrounding the Bahamas. Non-divers can simply stick on a snorkel and swim out from one of Nassau's gorgeous beaches, such as Cable, Jukanoo or Cabbage.

Flight is 3 hours and 10 minutes direct on United

Examples of itineraries from Chicago to Nassau recently found:
- $374 round trip on American from Jan 13 to Jan 16
- $374 round trip on US Airways from Jan 16 to Jan 18
- $387 round trip on United from Jan 16 to Jan 19
- Search for flights on your dates


2. Fly from Chicago to Montego Bay, Jamaica, for $326 round trip

Whether you opt to stay among the party streets and touristic hubbub of Montego Bay itself or venture out to the remoter beaches and resorts laced along the strands of western Jamaica, this indirect flight connection is your perfect ticket into town. Prices in the region of $325 round trip are common this winter, affording travelers the perfect opportunity to capitalize on the warm Caribbean weather. Direct flights depart out of O'Hare.

Top three reasons to visit Montego Bay:

  • The Hip Strip: Some love it, some loathe it, but if rolling, rambunctious nightlife is your thing, then the Hip Strip has it in barrels.
  • The nearby beaches: Montego Bay is frequently a crowded, sweltering city, but beautiful, breeze-cooled beaches are never far away. Cornwall and Doctor's Cave are the nearest.
  • The old colonial homes: Jamaica was turned into an island-wide sugar plantation by its British rulers. You can step into this troubled yet fascinating past at a number of old grand houses and plantations located in and around Montego Bay.

Flight is 4 hours and 25 minutes direct on American

Examples of itineraries from Chicago to Montego Bay recently found:
- $326 round trip on American from Feb 17 to Mar 10
- $339 round trip on US Airways from Feb 9 to Feb 13
- $421 round trip on American from Dec 15 to Dec 22
- Search for flights on your dates


1. Fly from Chicago to San Juan, Puerto Rico, for $282 round trip

The direct flight with American is the Chicagoan's ticket to the sun, sand and tropical terrain of Caribbean Puerto Rico this winter. Passengers can enjoy the popular sand stretches of San Juan, such as Condado and the Isla Verde and enjoy temperatures in the mid-80s while avoiding the harsh Chicago winter. Stay at a beach resort and have your pick of the best scuba diving spots, snorkeling reefs and surfing swells the island has to offer. for as low as $282 round trip, what’s not to like?

Top three reasons to visit San Juan:

  • The History: Founded in 1521, San Juan is America's second-oldest European settlement. A beautiful colonial Old Town is preserved for posterity between 15-foot-thick city walls, where palms sway outside pastel-colored houses shadowed by the crumbling turrets of 16th century Spanish forts.
  • The Salsa: Music drifts from every street corner in San Juan, mingling Brazilian beats, Latino folk, jazz and salsa in the warm evening air. But the city is most famous for its salsa scene, hosting several terrific clubs such as Nuyorican Cafe and Latin Roots.
  • The sea: Take a leisurely cocktail-fueled cruise round San Juan Bay, charter a fishing boat out into the salty blue, or head to the gorgeous urban beaches of Playa Isla Verde for watersports and snorkeling.

Flight is 5 hours and 15 minutes direct on American

Examples of itineraries from Chicago to San Juan recently found:
- $282 round trip on Spirit from Jan 25 to Jan 29
- $282 round trip on Spirit from Jan 25 to Feb 11
- $349 round trip on JetBlue from Jan 4 to Jan 13
- Search for flights on your dates

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