Our Travel Agents Craft Unforgettable

Caribbean Vacations

Sunset Travel & Cruise
Chicago IL, USA

From Chicago to…

the Caribbean

When you think of paradise, the Caribbean is probably one of the first places that come to mind, and for good reason – the beaches, the water, the opportunities for adventure. The choices are endless.

When you book a Caribbean cruise, resort vacation or any travel package with Sunset Travel & Cruise, you’ll get a personal travel agent who has been there, done that, and can help you plan the perfect vacation to the Caribbean from start to finish.

Vacation Travel Packages to the Caribbean - Sunset Travel & Cruise, Chicago IL

Offering up more than 7,000 islands, the Caribbean is home to countless tropical getaways that provide endless opportunities for adventure and relaxation. In fact, more than 30 million people visited the islands last year alone. 

Looking for hundreds of beaches? Maybe taking a cultural tour? How about going zip lining across a canyon? If you want to relax on the sand, learn the history of the land, or get your adrenaline pumping, the Caribbean is most definitely the place for you.

Whether you’re looking to explore the Bahamas or Jamaica, Puerto Rico or Dominican Republic, you can be sure that the expert travel agents Sunset Travel & Cruise are ready to make your vacation the trip of a lifetime.

IAmJaxx Sheard profile picture
IAmJaxx Sheard
1 year ago
Martha Galvez provided the best travel service for me when I booked my trip to Montego Bay, Jamaica. I treated my niece to the trip for her 21st birthday. Martha took the time to hear my plans and ensured all my requests were fulfilled. She was in touch with the resort and upon our arrival there was a birthday banner on the door, a slice of birthday cake and a bottle of wine awaiting us. I didn't have to do anything but tell Martha what I wanted. I'm truly grateful for her service as my travel agent. Thank you again Sunset Travel & Cruise AND my agent Martha Galvez!
IAmJaxx Sheard profile picture
IAmJaxx Sheard
1 year ago
Martha Galvez provided the best travel service for me when I booked my trip to Montego Bay, Jamaica. I treated my niece to the trip for her 21st birthday. Martha took the time to hear my plans and ensured all my requests were fulfilled. She was in touch with the resort and upon our arrival there was a birthday banner on the door, a slice of birthday cake and a bottle of wine awaiting us. I didn't have to do anything but tell Martha what I wanted. I'm truly grateful for her service as my travel agent. Thank you again Sunset Travel & Cruise AND my agent Martha Galvez!
Ryan planned a wonderful trip for my husband and I to Italy. He chose hotels we never would have knew about and made the experience seem less and easy. The company uses a helpful app where all our travel data was easily accessible while we were on the road!
Highly Recommend Ryan and his company for all your travel needs.

The pic is the view from the window of our hotel in Rome!
Ryan planned a wonderful trip for my husband and I to Italy. He chose hotels we never would have knew about and made the experience seem less and easy. The company uses a helpful app where all our travel data was easily accessible while we were on the road!
Highly Recommend Ryan and his company for all your travel needs.

The pic is the view from the window of our hotel in Rome!
Viviana Salgado profile picture
Viviana Salgado
1 year ago
Our travel agent Ryan Roman from Sunset Travel guided, coordinated and organized our dream wedding at Dreams Natura in Cancun Mexico on 10/26/24. My husband and I shopped around for an agent who could help us find exactly what we visioned as a destination wedding. He skillfully and patiently listened to our requests, followed through and delivered. Our wedding was amazing. From the location, to those who coordinated events and the staff who decorated and weighted on us hand and foot. It all turned out exactly how we wanted. Ryan took the time to understand what we wanted for our wedding. He communicated clearly, worked diligently with hotel staff, and responded in a timely manner with all my guests. I highly recommend Ryan for any future destination weddings or leisure traveling. We have kept in contact with him as we plan our future family vacation in April 2025.
FAQ: How Much Does it Cost to Go To The Caribbean?

While the cost of traveling to the Caribbean ultimately depends on many different factors, including the type of hotel, dining, activities and more, we’ll help you get an idea of the cost before diving in too deep…

$3,500

…is a great starting point for budgeting! 

This would include a 7 night stay for 2 people at average priced hotels or resorts, with moderately priced dining and activities. This estimate does NOT include airfare, so you would need to plan on that in addition.

TRAVEL EFFORTLESSLY WITH A TRAVEL AGENT!

Experience the Caribbean

  • Island Adventures

    Bahamas
    More than 700 islands spread out over 100,000 square miles of ocean offer endless tropical adventures.

    Dominican Republic
    There’s a good reason that more than four million tourists visit this island every year.

    U.S. Virgin Islands
    You get three islands in one – St. Croix, St. John, and St. Thomas – giving you big bang for your buck!

  • Cultural Experiences

    Jamaica
    If you love reggae, you’re going to want to take in the Bob Marley Museum!

    Puerto Rico
    Take in the endless miles of beaches or the history of Spanish colonial architecture.

    Aruba
    Home to beautiful sandy white beaches, 82-degree days, and some of the warmest people in the world.

Destination Weddings Spotlight

Planning a wedding in the Caribbean? Our experts can help!

Bahamas

This slice of paradise is perfect for destination weddings, a family vacation, or those looking for rest and relaxation on sandy, sunny beaches.

It’s an island that offers adventure, tropical escapes, and magical rainforests that are just as alive as any of the tropical animals that live there.

Watch the sunset over the Caribbean Sea, take in the tastes of island cuisine, and dance to the sound of slow reggae rhythms as you walk through the bustling city after a day of shopping.

Whether you’re looking for a resort vacation, cruise to the Bahamas or any type of travel package, call us for effortless travel arrangements!

Sunset Travel & Cruise can craft your perfect vacation, including:

  • White Witch Golf Course
  • Bob Marley Museum
  • Reach Falls
  • Montego Bay
  • Blue Lagoon
  • Seven Mile Beach
  • Dunn’s River Falls and Park
  • Blue Mountains National Park

Puerto Rico

Considered the most cosmopolitan place in the Caribbean, Puerto Rico is a variety of destinations in one – and perfect for any traveler.

You can spend the afternoon in the bustling, urban San Juan one day, take in a sunset on one of the golden sandy beaches that night, and then wake up and walk the cobblestone streets of Old San Juan, admiring its one-of-a-kind Spanish colonial architecture.

Easy travel, stunning beaches, world-famous rum, and one of the world’s largest river cave systems makes Puerto Rico a top Caribbean destination.

Contact Sunset Travel & Cruise to book your next vacation, effortlessly!

Some of the most popular activities in Puerto Rico include:

  • Bioluminescent Mosquito Bay
  • Flamenco Beach
  • Castillo de San Cristóbal
  • El Yunque National Rainforest
  • Calle del Cristo
  • Condado Beach
  • Museo de Arte de Ponce
  • Luquillo Beach

Dominican Republic

Every year more than four million visitors travel to the Dominican Republic, making it a top Caribbean vacation retreat – and for good reason.

There are a number of world-class hotels, resorts and attractions, not to mention people of the island have an incredibly welcoming attitude towards tourists.

There are miles of endless beaches, cities with amazing cuisine and shopping options, dozens of water sport adventures, and agro-tourism excursions where travelers can visit coffee, tobacco and cocoa farms.

We can arrange any type of travel package and tour itinerary in the Dominican Republic! Call us today for cruises, resorts and much more.

Some of the most popular attractions include:

  • Bavaro Beach
  • Los Haitises National Park
  • Saona Island
  • Scape Park at Cap Cana
  • Columbus Lighthouse
  • National Palace
  • Amber Cove
  • Cayo Levantado
  • Cathedral of Santa Maria la Menor

Aruba

Not only is this tropical paradise home to some of the warmest, most pleasant weather and sandy-white beaches in the world, but it’s also home to some of the warmest and most pleasant people that you’ll ever find.

Located 15 miles north of Venezuela in the warm waters of the southern Caribbean, Aruba offers up national parks, all-inclusive resorts, shopping, cacti and dramatic rock formations, and some of the most picturesque scenery that you’ll ever find.

Disconnect from the world and discover yourself in the warm turquoise waters and relaxing beaches of Aruba!

Sunset Travel & Cruise can help plan your perfect Aruba vacation, including activities such as:

  • Eagle Beach
  • Arikok National Park
  • Casino at Hyatt Regency Aruba
  • Hadicurari Beach
  • Ayo and Casibari Rock Formations
  • Philip’s Animal Garden
  • Fort Zoutman Historical Museum
  • Pedernales Wreck
Vacation in the U.S. Virgin Islands with Special Tour Packages from Sunset Travel & Cruise Agency in Chicago - Sunset-Travel.com

U.S. Virgin Islands

When planning a trip to the U.S. Virgin Islands, you get three amazing options – St. Croix, St. John and St. Thomas – that all offer a wide variety of activities.

More than two million visitors a year make the trip to take in everything from historical sites to national parks to active beaches, a bustling nightlife, and plentiful shopping and cuisine.

There’s snorkeling, hiking in the rainforest, museums, diving among coral reefs and so much to do, you’ll want to plan an extended vacation.

Fortunately, traveling between the three main islands couldn’t be easier – call Sunset Travel & Cruise to arrange your entire trip, including island hopping by ferry, plane or water taxi.

Some of the most popular activities include:

  • Virgin Islands National Park
  • Trunk Bay
  • Estate Whim Plantation Museum
  • Cruzan Rum Distillery
  • Sandy Point National Wildlife Refuge
  • Mahogany Run Golf Course
  • Divi Carina Bay Casino
  • Coral World Ocean Park
  • Paradise Point
  • Buck Island National Monument

CONTACT US TO CRAFT

Caribbean Vacation Packages

Sunset Travel & Cruise agents will guide you in making the best travel decisions!

Get the best options and the best deals on:

Flights & Hotels
Ground Transportation
Cruises or Resorts
Expeditions & Adventures
Restaurant Recommendations and Reservations

We’re here to help you every step of the way!

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Travel Agent

Insights…

“Aruba is one of the safest islands

to explore outside of your resorts. There are a lot of shopping and dining options within the main hotel strip of Palm Beach that is within walking distance.”

“Laid-back vacation vibes

get better when you’re island-hopping. After imbibing piña coladas, fly or take a ferry boat to another beach and shop, dine, and take in all that they have to offer!”

From the Blog

Travel Stories…

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