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
All-inclusives

Land Vacations

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River and oceanic
Europe
Alaska
Caribbean

Cruises

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Family & friends
Business meetings and conferences
Destination weddings

Groups

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

Expertise

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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.

Convenience

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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.

Problem-Solving

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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!

logos of the foremost family of travel agencies - foremost travel, windy city travel, oswego travel, traveloni, and lindstrom travel

Our Clients Say…

EXCELLENT
Google star 1Google star 2Google star 3Google star 4Google star 5
Based on 211 reviews
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Elizabeth Rendon profile picture
Elizabeth Rendon
Google star 1Google star 2Google star 3Google star 4Google star 5
Kathy is the BEST!! I'm so thankful that I found her. She went above and beyond resulting in an amazing adventure!!
Posted on Google Google
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diane calhoun
Google star 1Google star 2Google star 3Google star 4Google star 5
We truly had a wonderful experience in Athens, Mykonos and Santorini. Paros was a bit disappointing only because of the unpredictable winds. The Trip Plans app made all our connections and destinations seamless. Thanks for two weeks of amazing memories.
Posted on Google Google
Chris Clott profile picture
Chris Clott
Google star 1Google star 2Google star 3Google star 4Google star 5
Just returned from a wonderful trip to England beyond London. Lake District, Yorkshire Dales, York, Stratford Upon Avon, Oxford, Bath, Stonehenge, Southampton, Cotswolds', Blenheim Palace...Kathy and her provider team did an amazing job of arranging tours, transit and accommodations.
Posted on Google Google
John Hansen profile picture
John Hansen
Google star 1Google star 2Google star 3Google star 4Google star 5
Deni helped us book our first trip to Europe, and we had a lot of questions. He patiently took time to explain everything and organized things in an app so we had all the information we needed each day, as well as suggestions on things to do and places to visit. We couldn’t be happier and would gladly refer Deni and Windy City Travel to anyone looking to book a trip
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Greg Neri profile picture
Greg Neri
Google star 1Google star 2Google star 3Google star 4Google star 5
Dana did an outstanding job planning our two-week father-son trip through Paris, Berlin, Prague, Vienna, and Munich. Everything was well organized, the hotels and locations were excellent, and the itinerary struck a great balance between planned activities and time to explore on our own. Most importantly, the trip was truly memorable for my son and me. Dana was responsive, thoughtful, and a pleasure to work with. I would highly recommend her and would absolutely use her again.
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Corbin Schwalm profile picture
Corbin Schwalm
Google star 1Google star 2Google star 3Google star 4Google star 5
Dana was fantastic to work with from start to finish. She planned our honeymoon to French Polynesia, including Tahiti, Moorea, and Bora Bora, and the entire trip was seamless. We highly recommend the whale watching in Moorea. She put together an incredible itinerary, and was a great resource to handle changes during the trip. Dana made planning a major trip incredibly easy. We enjoyed working with her so much that we’re already planning to use her again for our next trip to Switzerland. Highly recommend!
Posted on Google Google
Vicki Tysseling profile picture
Vicki Tysseling
Google star 1Google star 2Google star 3Google star 4Google star 5
Cassie did an outstanding job planning our family's Summer 2026 vacation. Traveling with my husband and two teenagers can be challenging, but she took the time to understand our needs and customized every aspect of the trip for us. She made sure we had accommodations with plenty of space for our family, secured fantastic deals on both our cruise and airfare, and handpicked affordable excursions that were perfect for our interests. Every recommendation felt thoughtful and tailored specifically to us. Thanks to her expertise and attention to detail, our vacation was low stress, memorable, and exceeded our expectations. I highly recommend her services to anyone looking for a personalized travel experience.
Posted on Google Google
Regina Gallo profile picture
Regina Gallo
Google star 1Google star 2Google star 3Google star 4Google star 5
Kathy A once again planned a trip of a lifetime for our family to Greece. We spent time in Athens, Chios and Santorini. Our private tour of the Acropolis was spectacular. All our transfers, flights, hotels were perfectly chosen based on our requests. The Cliffside Suites in Santorini we beyond our expectations. All the hotels were in locations where we could immediately walk out and begin touring and enjoying our time there immediately. This follows our trip last summer which she planned when we went to Hawaii. We stayed in Maui and Kauai. Again, the most beautiful trip beyond our expectations and everything exactly what we wanted.

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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.