Experts In Adventure

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

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Expertise

Convenience

Problem-Solving

Expertise

Convenience

Problem-Solving

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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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

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

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

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.

Land Vacations

Land Vacation Search

Hotels and Resorts

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Cruises

Cruise Finder

River Cruising

Hot Offers

Where Are You Going?

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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  
   Based on 208 reviews 
    
 
 
 
   
 
 
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   Corbin Schwalm 
 
 
 
  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!
  
 
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   Vicki Tysseling 
 
 
 
  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.
  
 
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   Regina Gallo 
 
 
 
  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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   Bridget McCann 
 
 
 
  Highly recommend Karen! She was quick, responsive and had all the best reccomendations!
  
 
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   Somie Mossell 
 
 
 
  Cassie is the best! Everything went off exactly as planned. We had no issues with any of the tours, transfers, timeline, etc. It was perfect! The tours she picked were exactly what our group of 4 adults and 3 teenagers wanted to do. She added extra color commentary and suggestions on how to navigate Italy with a group of 7!
  
 
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   Kris Carey 
 
 
 
  This is the 3rd trip we booked with Cassie Thome at Windy City.  It was a 2 week trip to Italy (Rome, Florence and Venice) for two families with teenagers.  Cassie did a fantastic job of finding great accommodations, including a villa in Tuscany, and balancing activities.  The trip went wonderfully.
  
 
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   Avery Brennan 
 
 
 
  Deni Mayer was an excellent travel agent. ln one week's notice, he booked an entire two week trip to Europe that included Germany, Austria and Italy. I had never been out of the country before, and he made sure that I had the best trip of my life. Made all the planning for this vacation so easy and so that I could just focus on enjoying the vacation.
  
 
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   Paige 
 
 
 
  My husband and I just came back from the most unforgettable honeymoon in Italy, all thanks to Adam at Windy City Travel. From dinner reservations in Taormina to ferry tickets in Lake Como, Adam took care of all of our bookings with ease. The itinerary he created for us was incredible and so easy to access on the travel app he provided. We had the most memorable meals of our lives based on his F&B recommendations and the best excursions (e.g. winery tour  on the side of Mount Etna!). It truly was the best, stress-free trip ever, and we can't wait to work with Adam in the future.