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

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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!

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Our Clients Say…

Excellent
Based on 128 reviews
irene anderson
irene anderson
2024-05-13
The trip was absolutely fabulous. The resort was great. The airport here and in Punta Cana went without a hitch. All in all a wonderful time.
Amanda Munger
Amanda Munger
2024-05-08
My sister and I used Amanda here for a 2 week trip to Greece last year. She made the planning easy and did a great job finding amazing stays and transports for us. She was there for us throughout our planning, and while at times we felt like we needed more communication, it was clear once there she had exceeded all expectations. Our hotels we were always greeted with unique gifts and at 2 of the hotels, really nice room upgrades. We couldn’t have dreamed up a more perfect vacation, will be hard to ever trip this Greece trip. Highly recommend!
Sherry McAllister
Sherry McAllister
2024-04-29
We just came back from an amazing trip to Morocco! Kathy helped us create some magical days. We rode camels in the Sahara desert at sunset. We took a hot air balloon ride at sunrise outside of Marrakech. We hiked in the High Atlas Mountains and visited a Berber family. We tasted some great tagines. The English speaking guide and driver that she arranged were exceptional. From organizing our stay in beautiful and comfy hotels to setting up adventures, Kathy Allinson helped us plan and create many great memories.
Kathy Salinas
Kathy Salinas
2024-04-23
After a last-minute cancellation from a tour company I had booked with directly, I called Windy City Travel in a panic and Deni took care of me. Within just a few hours Deni was able to find a replacement Moroccan tour for me which was actually a much better tour AND I didn't need to change my plane tickets (booked through Dan at Windy City Travel). Both Deni and Dan were amazing. Will definitely continue to use Windy City Travel.
Jeanne Gallo
Jeanne Gallo
2024-04-04
Kathy has always done an amazing job planning our trips. For our trip to Prague, Vienna & Budapest she provided us with 3 hotel options for each city and several tour options. The hotels we selected were fabulous and we received an upgrade at each hotel. From the moment we arrived in Prague upon seeing our driver everything was seamless. Every tour guide was top notch and so very interesting. Kathy provided us with an app that had our entire itinerary so all we had to do was look at the app for our tickets, reservations etc. I appreciate that she gives us several options of things to do in each city. Kathy arranged all our transportation - train tickets, shuttle service to airports etc. We have been working with Kathy for 15 years and she never disappoints. She is great to work with and a pleasure to work with as well.
Kathy ross
Kathy ross
2024-04-01
Used their services for many years now. Domestic and international…couldn’t be happier! Amanda is great, she is responsive and has great advice. It’s great peace of mind to travel, knowing I have her experience and expertise, to ensure a successful vacation!!
Hailey Fleming
Hailey Fleming
2024-04-01
My husband and I have worked with Kathy at Windy City Travel several times over the last few years and have nothing but great things to say about our experiences. Kathy always seeks to understand our preferences and work within our budget when selecting hotels and excursions for our trips. The connections she has within the industry are hugely beneficial, and we always come back from vacations feeling like we had a trip curated just for us. I highly recommend working with Windy City Travel!
Christopher Meyer
Christopher Meyer
2024-03-30
We used Windy City Travel to plan our vacation in India. Deni was absolutely fantastic, always responsive, and was able to organize a great trip on very short notice. All the local guides and drivers provided were friendly and knowledgeable. It was great to have everything covered and not need to worry about anything. We strongly recommend Windy City Travel to anyone who wants a well-organized and headache-free trip.
Delphine Risto
Delphine Risto
2024-03-07
Cassie T. with Windy City Travel is a gem! I wanted to book my first ever cruise and she helped me figure out the best fit for me and my husband. She went above and beyond explaining the different aspects and what to keep in mind. She sent us gifts to our room on our anniversary and really made us feel special. 10/10 recommend her and look forward to working with her on our future travel plans!

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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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