Experts In Adventure

Let us share our knowledge with you to make your next vacation, destination wedding, honeymoon or event, your most memorable.

You Deserve the Thrill of Travel, Without the Hassle.

When you want to travel, you want to travel—not spend your time figuring out transportation, accommodations, excursions, or any of the thousand other details that are necessary for a truly special trip.

Chicago Travel Agency

As a premier Chicago travel agency, Windy City Travel understands the importance of personalized service and attention to detail. Our seasoned advisors have been around the globe and are ready to tailor a luxurious, hassle-free trip for you that will meet your exact needs and preferences.

Chicago Luxury Travel Agency

Whether you're looking for a romantic getaway or a corporate retreat, our Chicago Luxury Travel Agency experts will handle every detail, so you can focus on what matters most – exploring, experiencing, and enjoying your journey.

Give yourself permission to indulge in the ultimate travel experience. Explore. Experience. Enjoy.

Give yourself permission:
Explore. Experience. Enjoy.

Travel for All Tastes

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Escorted tours & safaris
Beach vacations

Land Vacations

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River and oceanic


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Family & friends
Business meetings and conferences
Destination weddings


Why Windy City Travel?

  • We have been serving Chicago travelers since 1981

  • We offer unbiased information on your best options for air, car, hotel, rail, tour and cruise

  • The power of the relationships we've built with vendors over decades is available to you with value-added amenties and supplier discounts

  • Our advisors have all traveled the globe and can often offer recommendations based on personal experience

  • We handle it all for you in a one-stop, easy shop

  • When weather strikes or plans have to change, our advisors seamlessly straighten it all out for you-a friendly face you can trust



Our travel advisors have access to a myriad of airfares, hotel rates, package tours, and cruise vacations worldwide.

Knowing where to look saves you time and money, so you can focus on enjoying your trip.



Travel insurance. Passports. Visas. Hotels. Shopping. Dining. Transportation. There's so much to worry about!

Our expert travel advisors handle it all for you, in an easy, one-stop shop.



Things go wrong. Plans change. Weather happens. Lots of moving pieces can make a vacation challenging!

Your travel advisor is always there to seamlessly straighten things out - a friendly face you know and trust.

Featured Travel Deals

Windy City Travel periodically offers travel deals in partnership with our travel providers. Please check back soon for the latest featured deals and offers, or browse all offers using the buttons below.

The Windy City Travel Family

Windy City Travel has partnered with Foremost Travel, Oswego Travel and Traveloni. This partnership allows our team to provide you with more travel benefits, exclusive offers, and additional services!

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Our Clients Say…

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  • Our destination specialists have stayed at or visited many of the resorts we recommend (unlike most online agencies). In order to best match your requirements with the array of resorts, packages and options available, we believe it is best for you to allow us to respond by speaking with you personally by phone about your contact request.
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