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

Land Vacations

River and oceanic


Family & friends
Business meetings and conferences
Destination weddings


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



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.



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.



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…

Based on 116 reviews
Chrystal Rimoldi
Chrystal Rimoldi
We worked with Kathy Allinson to plan our 3 week honeymoon to Australia and Fiji. She and her team planned a great mix of everything we asked for and then some. Will not hesitate to reach out again for guidance on our next big trip!
Julie Moon
Julie Moon
Cassie planned our recent cruise. We had lots of changes with our reservation and she was so helpful. We had not cruised on Royal Caribbean before and she was very patient answering our many questions. We were traveling with a group and everything came together very nicely. She planned a wonderful trip for us. I would highly recommend Cassie to help with your travel needs.
Carrie Hoza
Carrie Hoza
Cassie planned a fantastic cruise for me and 13 of my friends. Ages in the group ranged from 13-80 and there was something for everyone! So thoughtful in figuring out transfers to the ship, things to do during stops, and a special lunch at a specialty restaurant where we could all come together and dine on delicious Italian food. It was an amazing way to kick off 2024 and a ton of "big" birthdays within the group. I would go on ANY trip that Cassie planned!
Derek B
Derek B
Kathy helped us plan an amazing honeymoon to Thailand! We were struggling to find the time to coordinate it ourselves when we reached out to Windy City Travel. Kathy called us back to learn our preferences and budget. She had a detailed proposal within a week and her team was very flexible and easily modified it to meet our requests. The entire trip was amazing - the hotels were incredible, our local tour guides were terrific, and the excursions were a lot of fun. Every detail was accounted for - all we had to do was enjoy ourselves without any worries. We will definitely be calling Kathy again for our next big vacation!
We had an AMAZING trip (13 of us-3 families) planned by Kathy Allinson from Windy City Travel to Italy Summer 2023. We traveled for 12 days through Italy (Sorrento, Amalfi Coast, Rome and Florence) with 6 adults and 7 teenagers, and Kathy managed to find a balance of tours, activities, and food so that every person on the trip declared it the best trip of their lives! Door to door transportation and airport pickups, beautiful hotels, great locations everywhere for food and exploring, wine tours, Amalfi Coast tour that saved all three marriages for no one having to drive, cliff jumping for the teens, lazy pool days, private Colosseum tour, and attending Calcio Storico in Florence. There was so much more, but those were definite highlights. It was unforgettable, and Kathy did a great job working with us from budget to activities based on input. It was all organized and easy, with numbers for local vendors to assist if there were any problems. We can't wait to do another trip and will 100% be calling Kathy.
Crystal Gooch
Crystal Gooch
I have worked with Lynn and her team at Windy City Travel to plan multiple family trips over the last several years. Lynn has gotten to know our family, including our likes and dislikes, and curates an itinerary according to our preferences. Lynn’s knowledge and the team’s care and attention to detail gives me a level of confidence that makes the trip so much more enjoyable. Our most recent trip to Costa Rica 12/16/23 to 12/23/23 was wonderful. We stayed in the La Fortuna area and also on the Pacific coast. Both hotels were wonderful, the transport and guides with Memorable Costa Rica were top-notch, and the tours were breathtaking and educational! Highly, highly recommend Windy City Travel.
Kim Seay
Kim Seay
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
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
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
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.

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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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