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.

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

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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

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Hotels and Resorts

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Cruises

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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!

Our Clients Say…

Excellent

Based on 98 reviews

David Jimenez

2023-07-28

Amanda Hazen was amazing. She handled our many requests and adjustments with such grace, and displayed incredible patience and flexibility throughout the planning process. We would definitely use Amanda again for our next trip; not only was she incredibly knowledgeable, she also curated a list of amazing things to do during our stay in Barcelona. Consider working with Amanda for a stress-free traveling experience.

Jeff Darnell

2023-07-28

We just returned from Italy. Everything Windy City Travel planned for us was perfect - the flights, the pick-ups and drop-offs, the tours, train tickets - everything. Just a wonderful experience. We'll definitely use them for all our travel abroad going forward. Many thanks to their team!

Alice and Craig Lusthoff

2023-07-22

Having Kathy Allinson help us plan an itinerary and arrange transportation, lodging, and tours was key to our beautiful trip to Venice, Florence and Rome! Her caring goes beyond booking, as she called on our way to the airport to inform us of a pending train strike in Florence and how best to navigate our options. In Rome we decided to switch tours. A simple email to Kathy and she was right on it. You will not get this service and experience booking directly through the internet. Kathy’s experience and genuine concern for a great trip is invaluable!!!!! Thank you Kathy and Windy City for a most memorable experience!!

Regina Gallo

2023-07-21

Kathy A from Windy City Travel was very easy to work with and helped our family plan a 10 day trip to Scotland and Ireland which was spectacular. She gave us guidance, recommendations and options. She also was honest and steered us in the right direction in regards to our accommodations, day trips and full itinerary. She is an experienced traveler and was familiar with our destinations. We had a glitch with an airline ticket and their team immediately worked on resolving it while we went about our day. I highly recommend using Kathy for your next trip. We will definitely use her again.

Han Htoo Aung

2023-06-02

Jessica Paski

2023-05-26

Working was Lindsy was the best decision! She took all the stress out of planning a trip and she was very knowledgable about the best places to go. I really appreciated her help. Our trip was AMAZING! Thank you, Lindsy!!!

Jessica Vahey

2023-05-20

Kathy blended the perfect mix of comfort and activity into our 9 day trip to Scotland. Having never been to Scotland and going with my 80 yo mother, her help with selecting accommodations, activities, transportation and tours was invaluable. We celebrated our milestone birthdays while on this trip and the scenery, culture and people did not disapoint. We did not want to return home.

Al O’Connor

2023-04-28

Very well planned out timeline of the Amalfi Coast and Sicily! Highly recommend

Gladys Lopez

2023-04-21

Dana was great to work with. She listened and asked questions to understand what we wanted to do. She was timely in her responses, provided options and was extremely attentive to our requests. Dana shared insights and information into logistics we had not thought of and ensured every detail was covered. We had a phenomenal time and most importantly, were able to enjoy ourselves without worrying about details because it was taken care of.