Caribbean Bliss… You’re Invited

Take a quick trip to the Caribbean and warm your soul… and toes.  Visit islands like no other featuring astounding nature, intriguing history, and rich culture.

The Caribbean and Yucatan Peninsula are home to some of the best resorts in the world. From deluxe accommodations and a wide-variety of activities, these Caribbean hot-spots offer the best of all worlds: luxurious relaxation, unique and exotic experiences, and plenty of action for those that seek it. Big or small, young or old, Windy City Travel will ensure everyone on your trip has an unforgettable Caribbean vacation.

From the Dominican Republic to Jamaica and the Cayman’s, the Caribbean islands offer a fantastic combination of environments to capture your imagination and refresh your soul. Sugary soft beaches. Underwater cave explorations. Boutique shopping. Bonefishing adventures. Swimming with pigs. Every day in the Caribbean is exciting.

  • Nature in its Purest Form

  • Friendly Welcoming Culture

  • Adventure alongside Peace & Tranquility

Let us help plan the perfect Caribbean adventure for you. If you want to sip mai tais on the beach, we know the perfect spot. Want to do some deep sea fishing, we’ve got the charter for you.


With Windy City Travel, it’s more than just saving time and money, it’s ensuring you make memories that last a lifetime.

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Featured Caribbean Journeys

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Call us at (312) 951-0710 or fill out the short form below to start planning your next experience.

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Stuart Cove Shark Diving Bahamas

Stories from the Caribbean