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

home landvacations placeholder

Escorted tours & safaris
Beach vacations
All-inclusives

Land Vacations

home cruises placeholder

River and oceanic
Europe
Alaska
Caribbean

Cruises

home groups placeholder

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

benefits-expertise.jpg

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

benefits-convenience.jpg

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

benefits-problemsolving.jpg

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!

ForemostTravelGroup Logo

Our Clients Say…

Excellent
Based on 133 reviews
Chris Hemming
Chris Hemming
2024-06-02
Phil Agnew
Phil Agnew
2024-05-30
This was our first time working with Windy City Travel, and the experience was Wonderfull. Our plan was to visit Ireland, London, Paris, Normandy, and Belgium. We worked with Kathy Allinson and I have to say "impressive" is to small of a word to cover Kathy's experience, connections, planning and commitment to overall customer satisfaction! Kathy not only set up the perfect hotel accommodations but her relationship with all of the hotels made our experience a continuous VIP level. Her relationships in each country surpassed our expectations with every guide and tour she arranged. Every guide not only shared the top level tourist information, because of Kathy they spent more time and involved us in more of the culture and history of the area. Every tour seemed like a master class of the area and further peaked our interest to learn more and more. Kathy provided us with the trip of a lifetime and the joy we experienced cannot be fully expressed in this review. On a scale of five stars Kathy is a ten! Thank you Windy City Travel.
Leanne Burmeister
Leanne Burmeister
2024-05-21
Our honeymoon to Italy was the first time we used a travel agent, and we will only use Kathy and Windy City travel in the future. Kathy was kind, professional, and wonderful to work with and she has a very strong knowledge of Italy (having been there many many times herself) and has the perfect intuition on the details and rhythm of a vacation to Europe. The trip was absolutely fabulous. Everything exceeded our expectations and we could not have asked for more. Kathy even worked behind the scenes to get us hotel room upgrades and other nice surprises. The hotels, excursions, tour guides, recommendations, and the general itinerary were all excellent. Looking forward to booking our next adventure with Kathy and Windy City Travel - we could not recommend her or her company more - they are the best and we are very grateful they took such good care of us! Gary and Leanne
Nirali Trivedi
Nirali Trivedi
2024-05-20
My boyfriend and I just traveled to Italy for one week and had Kathy help us as our travel agent. We had the most amazing trip and it was all due to the amazing planning that Kathy did. She thought of every single little detail, including transport and sent us a very detailed itinerary prior to the trip, which helped us a lot! We did not have to worry about a single thing and will definitely be using Kathy again for our future travel! Would recommend her services to anyone planning a trip!
Kate Bensen
Kate Bensen
2024-05-14
Kathy Allison found us the perfect hotel in Paris! I look forward to working with her again.
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.

Get Started

  • 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.
  • Hidden
  • Hidden
  • Hidden
  • Hidden
  • Hidden
  • Hidden
  • Hidden
  • Hidden
  • Hidden
  • Hidden
  • This field is for validation purposes and should be left unchanged.