Discover Off the Beaten Path Destinations

Are you ready to escape the ordinary and dive into the extraordinary? At Windy City Travel, we’re all about crafting unique travel experiences that whisk you away from the hustle and bustle, revealing hidden gems and lesser-known wonders of the world.

These days, everyone seems to be bitten by the travel bug—and why not? From remote home offices, we at Windy City Travel are busy breathing life into the kind of journeys that inspire wanderlust. Whether it’s through a serene tropical escape or a tranquil European hideaway, our goal is to bring the world to you in all its vibrant and unexpected glory!

Recently, we teamed up with Classic Vacations, known for their off the beaten path adventures and sustainable travel opportunities. Together we hope to spread the love of exploration beyond the typical tourist hotspots. Get ready for adventures that are not only thrilling but also ecofriendly!


Delve into Costa Rica’s Wonders

Picture lush rainforests, teeming wildlife, and a commitment to sustainability. Costa Rica offers you the chance to uncover new horizons while maintaining a gentle footprint on the planet.

Explore the Quieter Side of Hawaii

Imagine stepping into a piece of paradise that isn’t overrun with tourists. Experience the serene beauty of Lanai and the untouched expanses at Andaz Maui at Wailea Resort. In these tranquil havens, the only rush you’ll feel is from your own excitement!

Embrace Tranquility in the Italian Dolomites 

Swap the crowded streets of major cities for the peaceful embrace of Italy’s Dolomites. Marvel at the towering peaks and enjoy the silence and solitude that beckon at resorts like Pina Dolomites—it’s a world away from the typical tourist shuffle.

Uncover Magic in Mexico

With its vibrant culture and colorful landscapes, Mexico is a treasure trove waiting to be explored. Our current favorite spot? The charming town of San Miguel de Allende. Whether you’re savoring delectable cuisine or meandering through picturesque streets, this locale promises an unforgettable experience.

At Windy City Travel, we believe in the power of travel to transform and illuminate. So if you’re ready to embark on an adventure that takes you beyond the familiar, give us a call at (312) 951-0710 or contact us here.