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.
Sugary soft beaches. Underwater cave explorations. Boutique shopping. Deep sea fishing adventures. Swimming with pigs. Every day in the Caribbean has something exciting in store.
The Yucatan Peninsula and Caribbean islands are home to some of the best resorts and activities in the world. These vacation hot spots offer the best of all worlds: luxurious relaxation, exotic experiences and plenty of action for those who seek it.
From the Dominican Republic to Jamaica and Saint Lucia, the islands of the Caribbean and Yucatan offer a fantastic combination of environments to capture your imagination and refresh your soul.
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.