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Chicago 5 Star Resorts

THE BEST 5 Star Resorts in Chicago

Chicago 5 Star Resorts

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Travellers’ Choice Awards winners (including the “Best of the Best” title) are among the top 10% of listings on Tripadvisor, according to the reviews and opinions of travellers across the globe.


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Showing results 1-30 of 1,261

Popular destinations for 5 Star Resorts

  • Orlando
    From the Magic Kingdom to magical spa treatments, Orlando sparkles with the promise of adventure. Spend a day exploring the world-famous Disney theme parks or screaming your head off on a Universal Studios roller coaster. For a less adrenaline-pumping afternoon, enjoy the quiet natural beauty of the Harry P. Leu Gardens or enjoy a seaweed scrub at a luxury day spa. Savor fresh and local ingredients at one of Orlando’s James Beard-nominated restaurants.
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  • Sunny Isles Beach
    Located on the southeast tip of Florida, Sunny Isles Beach is set on a barrier island surrounded by the Atlantic Ocean and the Intracoastal Waterway. Halfway between Miami and Fort Lauderdale, Sunny Isles Beach is the perfect relaxing escape and includes two miles of fine sand. Visit the landmark fishing pier or enjoy the area's abundant outdoor activities, such as snorkeling.
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  • Cuba
    U.S. citizens still need to jump through a few hoops to visit Cuba, but as visitors from around the world know, this island offers some amazing opportunities for cultural exchange. Havana is a mix of old-world architecture and of-the-moment culture. Head out of the capital city to the small town of Trinidad to see more Spanish colonial architecture. It’s a UNESCO World Heritage Site and a fantastic home base for a visit to the Valley of the Sugar Mills, a pocket of land that formerly served as the centre of Cuba’s sugar industry.
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  • Dominican Republic
    The Dominican Republic lies in the same waters as Cuba and Puerto Rico, taking up the eastern two-thirds of the island it shares with Haiti. Offering a lush interior with a mix of caves, Victorian gingerbread houses and the lore of pirates, plus 900 miles of coastline along its brim, island highlights include riding a cable car up Mount Isabel de Torres and basking on stunning Saona Island. Oh, and did we mention the D.R. is family-friendly, has just about perfect weather and is affordable?
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  • York
    Just two hours north of London by rail, the city of York holds 1900 years' worth of history in its ancient walls. The Romans built the city in 71 AD, and the Vikings captured it in 866 AD. Stop by the Yorkshire Museum and Gardens for a look at what the Roman and Vikings left behind (they must have packed light when they left). From there, move on to the York Castle Museum for a not-so-quick overview of the most recent 400 years.
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  • Lagos
    There is rich and beautiful history within Lagos’ 14th century walls, from its fortress to picturesque churches like mediaeval São João Hermitage and the 17th-century São Sebastião. But that’s all appetiser. People come here for a main-course coastal buffet featuring more than a half-dozen beautiful beaches. Quiet sandy coves are sandwiched between dramatic cliffs. The sandy 2.5-mile stretch of Meia Praia caters to every water sport imaginable. And when you’ve had your fill, you can digest your day with some of the best nightlife in the Algarve region.
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  • Playa d'en Bossa
    Ibiza’s premier party destination, Playa d'en Bossa draws A-listers and music lovers with its hip bars and thrumming clubs. But there’s more to this resort town than all-night raving–Ibiza’s longest beach harbours water sports facilities and relaxed restaurants, while a waterpark offers plenty for families, too.
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  • Salzburg
    It’s been 200 years or so since he lived here, but Mozart is still very much Salzburg’s favourite son. Visit the composer’s residence and birthplace, then explore the Altstadt (Old City), taking in the baroque architecture. If your musical tastes run more "Raindrops on roses and whiskers on kittens" than "Requiem in D Minor," catch one of the many Sound of Music tours and follow in the footsteps of the Von Trapps.
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  • Varde
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