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This Week’s Deals
This Week’s Deals

WHO ARE WE ?

Windy City Travel is a Full Service Travel
Agency operating from Chicago, IL.

Windy City Travel has been in business as a full service travel agency in Old Town since 1981. The staff is renowned for providing personalized service for all your corporate and leisure travel needs – including, destination weddings, honeymoons, vacations, family reunions, groups and incentives. Our corporate agents are veterans at corporate travel and our leisure agents have traveled the globe and are able to provide information, details and suggestions to truly tailor a vacation, wedding or honeymoon to meet your needs and preferences.

In our aim to provide the best service, we offer you unbiased information on your best air, car, hotel, rail and cruise options. Our preferred relationships will be available to you with value-added amenities and supplier discounts.

We also specialize in destination weddings throughout the world. We make sure that every detail is covered to make your destination wedding a stress-free experience. Our vacation planning services will take care of your getaways and coordinate a customized itinerary. Services also include cruise, air, car, hotel, rail, transfers and sightseeing to the destination of your choice. Every element of your trip is reviewed to maximize your discounts.

Let us share our knowledge with you to make your next vacation, destination wedding, honeymoon or event,  your most memorable. Contact us today for a free consultation!

OUR SERVICES

Our team of travel experts offer top tier travel services for mouth watering vacations, destination weddings and honeymoons, and corporate travel management. From adventurous elephant trekking to awe-inspiring beaches, our collection of destinations is irresistible.

Vacations Wedding Planning Group Vacations
Corporate Travel Honeymoon Services Cruise Planning

Platinum Service

We have a longtime reputation for catering to Hollywood’s and Chicago’s A-list, music legends, TV personalities, and professional athletes.

You only want the best for the value. First class airfare at discounted rates, private jet or yacht charter. As a discerning traveler, you know and appreciate luxury. Your standards are high – when traveling, you want the best and most compelling trip possible. At Windy City Travel, the staff’s decades of experience will fulfill your every wish. Every detail will be anticipated and included.

Meet your driver and guide upon arrival for a first glimpse of the Tuscan countryside or jump in a European sports car to tour the lavender fields of Provence. Stop at a local vineyard where the family offers you a taste of their finest reserve wines and champagnes and stay at a chateau or a villa where you will learn the art of fine cooking. Enjoy secluded private islands with a personal chef in Fiji or a one-on-one butler service and a concierge who knows your unique taste, in London, Hong Kong, or Rome.

Travel enjoying the highest standards of comfort and service courtesy of Windy City Travel.

Free Consultation

Featured Deals

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“Mary made this whole experience phenomenal – we had very few days to plan a big vacation and she was very responsive and listened to what was important to us in a resort. The booking process was seamless and fast. I will definitely come to her again and recommend her to others!!!”
Nina G., Chicago, IL
“Absolutely above and beyond everything we hoped our 35th anniversary trip would be. All reservations seemed to have changed times as we got closer. They made sure we knew of every change. We were thrilled with everything. Thank you again!
Robin S., Deerfield, IL
This is the second year in a row that we’ve booked our vacation through Windy City. We’ve worked with Lynn and she’s been great about answering our questions and meeting our needs. She listened to what we wanted in a vacation and her recommendation for resorts is spot on!
Donna D., Plainfield, IL

TRAVEL BLOG

When it comes to our advice we’re proud to say we’re different. We offer something a little more special.

Singles in Melbourne, Australia

Australia is one of the most inviting, friendly and exciting destinations in the world, and all those things are just as true generally as they are for singles visiting the city of Melbourne. Best of all, everyone speaks English here, which makes traveling easier and also opens up welcome doors for the solo explorer.

LGBT Vacations in Sitges, Spain

Being located in Spain and a part of the EU, the small city of Stiges would necessarily register as a very LGBT-friendly destination. However, it is an exceptional gay paradise that is quickly finding its feet and challenging some of the more established and renowned vacation spots in the region.