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.

And nothing kills the mood of a vacation faster than dealing with unexpected changes or disruptions.

Whether for leisure or corporate travel, the seasoned advisors at Windy City Travel have been around the globe and are ready to tailor a trip for you that will meet your exact needs and preferences.

Give yourself permission:
Explore. Experience. Enjoy.

Travel for All Tastes

Escorted tours & safaris
Beach vacations
All-inclusives

Land Vacations

River and oceanic
Europe
Alaska
Caribbean

Cruises

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!

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Our Clients Say…

Excellent
Based on 110 reviews
Kim Seay
Kim Seay
2023-11-21
When we decided to go to Italy for our honeymoon, I was a bit overwhelmed with the planning. So we reached out to Windy City Travel for some help. I had never used a travel agent before and being a bit of a control freak, I was a little nervous about letting someone else plan our trip. Our agent, Kathy, told me at one point that I would wonder why I never used a travel agent before, and she was absolutely right! She planned a fabulous trip for us where we visited Florence, Rome and Naples. The hotels were superb; the tours were absolutely amazing; and everything was perfectly organized and went off without even a single issue. If anyone reading this is on the fence about using a travel agent to plan your next trip, my advice would be to call Kathy at Windy City Travel and enjoy the trip of a lifetime!
Tw Miller
Tw Miller
2023-11-19
Traveling abroad can be challenging at best and overwhelming at worst. Which is why my partner and I contacted Windy City Travel for help planning a 10-night trip to Italy. And help is what we got from travel advisor Deni Mayer, who immediately shared his years of experience, knowledge and passion to work on our behalf. He booked hotels, flights and additional transportation within the country, along with a few tours we were interested in. The great thing about Deni is he listened to what we wanted (even when we changed our mind about this, that or the other) and then calmly went about fashioning the experience we desired. Here's the other important thing: he was always available by phone and email and even Zoom. He forced nothing on us, but instead worked to make us happy. We had a wonderful trip. Thank you, Windy City Travel and thank you, Deni Mayer.
Corky Bellile
Corky Bellile
2023-11-16
What a phenomenal trip we had to Portugal, thanks to Kathy Allinson at Windy City Travel! I provided her with "asks" and she did all the heavy lifting to make the trip an incredible experience. From the hotels to tours to other recommendations, she did it all with exceptional results! This is my third trip abroad planned by Kathy and I'm consistently grateful for her skills and excellent customer service. I highly recommend Kathy to plan your next trip!
georgia tauscher
georgia tauscher
2023-11-03
Kathy has scripted 2 trips for us and we have been so happy with her attention to detail and to finding personalized activities that we have enjoyed immensely. She has contacts that we never would find thru our own searches and the peace of mind that it gives us to have her there if anything goes awry is huge.
Ryan Larson
Ryan Larson
2023-10-29
Kathy A. at Windy City Travel is simply amazing! She has helped our family plan trips from Italy to Greece, Spain and Portugal, Egypt and everything in between. Kathy is knowledgeable, responsive, spot on, gets things done, and leaves no details behind. Thank you for everything, Kathy!
Jennifer Gramann
Jennifer Gramann
2023-10-28
Kathy made this dream trip come true for me and my daughter! Everything was taken care of and delivered electronically with ease. We had amazing tours, local exposure and we were truly immersed in our Italy experience! I look forward to using Windy City Travel again for my next adventure!
Beth Wood
Beth Wood
2023-10-28
We had a trip of a lifetime! We spent time in London, Edinburgh and Lisbon. At each location we experienced wonderful accommodations, outstanding tour guides and smooth seamless travel arrangements all thanks to our fantastic travel agent Kathy. We realize her expertise is what made the difference. We highly recommend Windy City Travel and Kathy. We’re looking forward to planning our next vacation!
Mark Androw
Mark Androw
2023-10-25
Kathy Allinson planned the trip of a lifetime for us. Every detail was perfect.
Ashley Karadsheh
Ashley Karadsheh
2023-10-16
If you are planning a honeymoon please consider Windy City travel!! We were helped by Deni to plan our honeymoon in Bali (he specializes in Southeast Asia, so request him if that’s where you’re going). It took all the stress out of planning, which honestly after planning a wedding there’s no way we could have planned both. Each day was planned to PERFECTION and all airport transfers, airline changes and hotels were handled by him and it was SO smooth. We even got a bunch of free perks (free food vouchers) and free upgrades based on the company’s good standing with the luxury resorts. Below are a few pictures from our excursions deni set up for us. We had the time of our life and it was the perfect de-stress after our wedding day. 🙂
Aurora
Aurora
2023-10-11
I highly recommend using Windy City Travel to plan your next destination trip. With the help of Kathy A. from Windy City Travel, I was able to have my dream trip to Greece come true. We were able to experience the many different parts of Greece; Athens, Mykonos, Paros and Santorini. This was my 1st time out of the country and was so nervous and did not know what to expect. Kathy made all the arrangements for our transportation and hotels and even booked a tour of the Acropolis in Athens. Everything on our trip worked out seamlessly and exceeded my expectations. I was very pleased with my experience as Kathy made it stress free, and I will definitely be using Windy City Travel again for my next trip!

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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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