Who is Windy City Travel

Let us share our knowledge with you to make your next vacation, destination wedding, honeymoon or event, your most memorable.

Windy City Travel has been in business as a full-service travel agency in the Old Town neighborhood of Chicago since 1981. The staff is renowned for providing personalized service for all your leisure and corporate travel needs including vacations, group travel, honeymoons, cruises and destination weddings. Our advisors have traveled the globe and are able to provide information and suggestions to truly tailor a trip to meet your needs and preferences.

In our aim to provide the best service, we offer you unbiased information on your best air, car, hotel, rail, tour and cruise options. Our preferred relationships will be available to you with value-added amenities and supplier discounts.

Problem Solving
Supplier Relationships

Where would you like to go?



Australia & New Zealand



North/Central/South America

What type of trip are you planning?

vacation planning

Land Vacations

Escorted Tours & Safaris, Beach Vacations, All Inclusives

cruise planning


River and Oceanic. Europe, Alaska, Caribbean

group travel and vacation planning


Family & Friends, Business Meetings & Conferences, Destination Weddings

Windy City Travel IconWindy City Travel

1357 North Wells Street, Chicago

4.6 87 reviews

  • Avatar Pauline Festa ★★★★★ 4 months ago
    Can't sing enough praises for the trip planned by Lynn and her staff. Across 3 states - Colorado, Utah, and Nevada - the trip was an amazing memory for our 30th Anniversary. Lynn did not just book flights, car and hotels, but recommended … More activities and restaurants along the way so we didn't have to think about much. Highly recommend!
  • Avatar James Kirk ★★★★★ 5 months ago
    Amanda at Windy City Travel did a fantastic job of arranging our 3 week honeymoon in Italy. We visited a number of different cities and Amanda picked great hotels in each city that were within our budget and also arranged all of our train … More travel and tours/excursions. We changed our plans a couple of times and Amanda was very helpful in accommodating our changing plans and updated the hotels to match. Everything went really smoothly. We would highly recommend the services of Windy City Travel!
  • Avatar Alexandria Santella ★★★★★ 5 months ago
    Kathy planned our honeymoon to Germany and Italy fabulously! It was so nice to meet with her and discuss our hopes for the trip - and then she ran with it beautifully. We didn't have a single mishap or complaint the entire 10 day trip. … More Will definitely be asking Kathy to plan all our trips abroad in the future!
  • Avatar Erica Jay ★★★★★ 4 months ago
    Amanda is such an amazing travel agent! She assisted me with last minute travels to Paris a few weeks ago. She is very attentive to your needs and she made sure I had a smooth easy trip afterwards to personally call me and ask. She has … More excellent customer service and on top of that is very professional, timely and enthusiastic to help you find whatever you need for your travel experience.
  • Avatar Kay Truffelli ★★★★★ 4 months ago
    Kathy Allinson of Windy City Travel did a fantastic job helping us plan the trip of a lifetime to Italy for 2 weeks. Kathy helped us plan all of the hotels, tours, transportation, train tickets, etc., and then we had to postpone due to … More to Covid 2 1/ 2 years ago. We decided to go this September, and Kathy picked right back up on the all of the details of our trip, and re-booked everything, and it was the best trip ever, in every way! The hotels were wonderful, great locations and amenities, and always a fabulous view. The itinerary was perfect, tours were wonderful, so great to have all of our transportation pre-arranged including train tickets, drivers, and a rental car. We would recommend Kathy and Windy City Travel, and definitely hope to travel again soon and will call Kathy for sure!
  • Avatar Parrish Harris ★★★★★ 10 months ago
    I worked for weeks trying to plan the perfect first Caribbean vacation for me and my boyfriend. After much frustration and trying to figure out if I was finding the right places, if the prices were right, and if the flights would be too … More expensive, I decided to find a travel agent. I found Windy City Travel based on reviews, and was I glad I decided to reach out to them. Our travel agent Lindsy was so great to work with! We had one conversation and I told her my travel desires and she took it from there. She was very accommodating and got several packages together for us right away! We had our first of many AMAZING vacations and can't wait to book more! Unfortunately our phones got wet on one of the bar cruises we went on and we didn't get many pics but our first trip to Jamaica was everything we dreamed it would be! We're already looking forward to our next vacation adventure and booking with Windy City Travel!!
  • Avatar Alexandria Hawkey ★★★★★ 5 months ago
    Kathy planned our honeymoon to Germany and Italy fabulously! It was so nice to meet with her and discuss our hopes for the trip - and then she ran with it beautifully. We didn't have a single mishap or complaint the entire 10 day trip. … More Will definitely be asking Kathy to plan all our trips abroad in the future!
  • Avatar Dawn Wurst ★★★★★ 9 months ago
    When your vacation time is valuable, only trust the planning to the very best! We just returned from our 3rd European vacation in the last 8 years planned by Kathy Allinson and she did it AGAIN! We had a tall order this time- plan a trip … More in 3 very diverse areas (Prague/Dolomites/Spain) at the request of family members), and make it a trip that everyone in our active family would enjoy. She came through with flying colors- arranging all tours, hotels, transfers, air, rental car, and rail transportation to get us where we wanted to go. We had the 2-week trip of a lifetime! Also- when an airline cancelled our flight from Amsterdam to Prague, Kathy and team worked on the weekend to readjust our tours and transfers to ensure we kept as much of our vacation intact as possible. We so appreciate her attention to detail, customer service, and excellent knowledge and suggestions about European travel. Definitely call her if you're thinking of making a trip!
  • Avatar Evan Huss ★★★★★ a year ago
    I came across this site and was paired with Sandi- She did an amazing job! I am a senior in college, and I was in charge of figuring out a cheap/fun spring break trip. She found the perfect trip that was in our budget! She also was great … More at responding quickly when we had questions and issues
  • Avatar Monica Schrager ★★★★★ 8 months ago
    This was my first time using a travel agent and I was glad I did. Paula was great explaining the process, sharing options and recommendations, and taking care of all those details that I've previously done on my own and found overwhelming. … More We had a couple minor hiccups during the trip that were easy to manage and I shared with Paula at the time and she responded quickly to follow up. Overall a great experience and I'd use Paula again.
  • Avatar Nancy McHugh ★★★★★ 7 months ago
    We worked with Kathy at WCT to book our honeymoon to the French Riviera and Provence. We are so happy that we chose to work with a travel agent for our trip. Having always booked my own travel through expedia and other sites, I always thought … More I was finding the best "deals" - I had no idea that there weren't fees associated with most travel agencies and that you can actually save money (or get free upgrades) when working with one. I will never book a big trip without working with Kathy again! Whether you have no idea where you want to travel, or you know where you want to go but need help with booking, suggestions, support with logistics, etc, they can help you! I cannot say enough good things about how responsive and helpful Kathy was and we look forward to booking another trip with WTC in the future.
  • Avatar Tracey Hooks ★★★★★ 7 months ago
    I love using Windy city for my travel needs. They arranged my transportation to and from the hotel in Vegas and I felt like a celebrity!!Everything was top notch!!

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