We finally did it! Our family trip to Europe. Our boys are big history buffs like my husband and asked for a trip to Europe to visit specific sites/locations they chose. We decided to start planning and quickly realized we were over our heads. We found Windy City by searching online. Dana did an amazing job of listening to our wants/needs while guiding us to make wise choices as we went along. It was a terrific trip that we will never forget and we are on to planning our next two trips with her already. read more

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Windy City Travel helped us arrange a trip to London. Paula was very helpful in putting together our travel plan. Her assistance made the trip run smoothly and left us to enjoy a great experience in London. read more

I received exceptional follow up after an earlier review that was less than five stars. It seems there may have been some sort of technical glitch and this company clearly cares about its reputation. Given my recent experience, I would try them again. read more

Cassie worked hard to find me an amazing inside passage cruise with Silver Seas. It was a great value, and a 5 star experience. Thanks Cassie!!! We had the best 20th Anniversary... read more

Windy City Travel - Glacier Bay - Travel Services Near Me - Chicago, Illinois

This year, with additional vacation time, I decided to plan our very first trip to Asia. Being seasoned travelers, we usually plan our own trips. However, since this was our first time visiting this part of the world, I enlisted the help of Deni at Windy City Travel. This was a three-week trip for my whole family across Singapore, Bali, and Vietnam. Deni assisted us in crafting a well-structured itinerary, booked very professional guides for some of our day trips, and offered excellent advice on where to stay and which sights to prioritize in each country. The suggested hotels in each city were all top-notch and ideally located. I'm happy to say our trip was amazing. Our kids loved it, and my wife kept commenting on how smoothly everything went and how well-planned it was. I highly recommend Deni and Windy City Travel and look forward to booking more trips with them in the future! read more

Our second time using Kathy with Windy City Travel & could not be happier! Reached out to Kathy last minute to help us escape the February cold & in a few weeks she put together an amazing trip to Cartagena, Colombia. We stayed at a beautiful hotel with ocean views and close enough to the Old City of Cartagena. We are looking forward to Kathy planning our next trip! read more

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Lynn and Windy City Travel were organized, responsive and professional throughout both the planning process and while on our honeymoon. It was a three-week trip in 6 different cities across Italy and Greece and the trip went smoothly from beginning-to-end. 5/5 stars and I highly recommend Lynn and her team to plan any trip needed. They listen to your vision and make it happen. Thanks to all at Windy City Travel. read more

We used Windy City Travel to help plan our family vacation to Greece. Michele was great helping me plan the trip with awesome suggestions on itinerary, logistics, resorts and activities. She made sure we were well taken care of and we enjoyed every minute of our trip. Their experience was invaluable to help us comfortably navigate a foreign country and experience a true Greek holiday! read more

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! read more

Sandi planned a wonderful Ireland trip for my daughter and I! I wouldn't have changed a thing! I told her that we wanted a balance of structured tours and free time to explore and see things on our own time and it worked out great! There was also great local help if needed - I really only needed to make one local call to move back out arranged transportation by a couple of hours, as we wanted to sightsee more. Would highly recommend this service! read more

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Amanda was fantastic to work with as she's now helped me with two major trips. First helped select the perfect Cancun resort for me and 12 friends back in Nov. 2022. She listened to my wants and needs and selected the perfect resort. She booked flights, resort and transfers it was seamless! My friends loved the simplicity of it as well! I then used Amanda for a second time and for a trip of a lifetime - 2 weeks in Italy! Once again, she listened to my wants and needs and found us fantastic hotel and apartment options that were in heart of the action, but with a cool art-twist that I don't think i would have found on my own! She secured all our trains and transfers which was an enormous help when trying to plan such and extravagant trip for 3 adults! 100% recommend working with Amanda! read more

Dana planned our honeymoon with a lot of creative freedom and it ended up being absolutely amazing. 2 countries and 4 cities in 8 days, never felt rushed or overwhelmed! Everything was so organized and detailed. All of our hotels were wonderful and walking distance from either airport or train station, while also being a central spot for exploring via walking. Highly recommend :) read more

My husband and I reached out to Windy City Travel last summer as we began to plan a 3-week family vacation that would also include my father to Ireland, Scotland, England and Spain. Kathy Allinson did an excellent job of booking our flights, hotels, and excursions every step of the way. Each time we checked into a hotel, it was clear that the management was familiar with her and we were always treated exceedingly well. The real value to working with Kathy became apparent when American Airlines had to cancel our flight to Ireland after we'd already begun our travels. Over the course of the first 72 hours of our vacation, Kathy worked tirelessly behind the scenes to get us rebooked and to amend our hotel reservations as the early days of our trip fell apart. With her support, we were able to actually make something good out of an unplanned 48 hour layover in Philadelphia, knowing that she was working on our behalf behind the scenes. We look forward to working with Kathy again in the future and highly recommend her services to other travelers. read more

Patsy is amazing! I will plan my next holidays with her for sure! She was super helpful and nice and really paid attention to all our requests. read more

We couldn't have been happier with our trip to Portugal -- it was everything we hoped it would be. Paula spent a lot of time talking with us about our hotel preferences, what we wanted to see, and how we organized our days when traveling. She chose hotels that were very good and in great locations in the four cities we visited. She also arranged a couple guided tours and drivers to meet us at the airport and take from city to city. Everyone we dealt with was excellent. We had a European contact who checked in before each tour or change of location and who was available if there was a problem -- fortunately it was a trouble free trip. In all it was a customized tour for the two of us. We would definitely use Windy City and Paula for future travel. read more

Michelle over at Windy City Travel was excellent, nary a glitch our entire vacation.

WOW.. Loved how this got handled! You have to love then the company's president reaches out to you to make things right! Lynn helped us get our trip booked and I can't wait to go! read more

Windy City Travel was recommended to me years ago and I never made the call. I had to get my daughter to college in California and had the airfare booked but got really busy at work. I was worried I would forget something so I called them. I spoke with super friendly and equally efficient Amanda to get me a room and a rental car. I decided to even go with insurance during these uncertain times. The trip was flawless and given the low fee they charge for booking, I will use them a lot more going forward and suggest you do the same. I had a friend who used a discount site to book a room for her and her family and when they got there the hotel had nothing for them. With Windy City, they could have called their help line and gotten immediate, personal help. read more

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 Collesseum 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. read more

Lynn Farrell is a true pro. During the pandemic that will likely change how we all view travel moving forward, Lynn stuck with me to schedule a complicated trip. She then rescheduled it several times as the country we're visiting closed to US visitors, changed entry requirements and everything in between. We're cautiously optimistic that THIS time we'll actually get to the desired destination, but if we don't...I know Lynn will stick with me until we do. She's super responsive, light hearted and a joy to work with. Thank you Lynn!! read more

I was really hopeful that this agency would be my "go-to" but unfortunately my experience is similar to other bad reviews. I called and spoke to OWNER, Lynn. Gave her my info for what I was looking for with the travel plans. She assured me she would send the info to one of her agents and they would contact me on Monday (I talked to her on Friday). Well, Monday, Tuesday, and Wednesday came and went with no phone call so I called and checked in. The rep tried finding me in the system and couldn't find any info that I left with Lynn. Lynn was busy traveling (ironic) so her staff couldn't get a hold of her to see if she started working on my travel plans. The rep I spoke to had me repeat all of the info, travel locations, number and age of travelers, travel dates, budget, etc. And someone would be in touch. 20 minutes later a different rep called me and had me repeat AGAIN all of the travel plans so she can get started on my trip. Okay, I'm a very patient person so for the 3rd time, I went over the info and was told she would get to work on it and call me on Monday. I get a call from a gentleman this time, on Monday, as they promised, and I'm sure you can guess what the details of the call were...? To confirm my travel plans! You guessed it! Travel locations, number of travelers, budget, etc. When I told the rep, I have now spoken to 4 different people and have had the exact same conversation with nothing actually being done yet, he said "well, your budget is $5000 per person and that's not enough". For the record, I already have a quote of $4850 per person and I am shopping for the best plan, price & experience I can get, but after just how unorganized and just how much of my time these people wasted, I would NEVER trust them with an abroad trip for elderly family members even if I would increase my budget! Save yourself the time and go elsewhere. read more

I worked with Amanda to plan our trip to Tulum, Mexico. She was very knowledgeable on the area and had great recommendations. We booked flights and a boutique hotel with her and we loved our accommodations! I'd recommend her to anyone and I look forward to working with her again. read more

Lynn was really helpful and booked an awesome trip to the Maldives through Dubai for my honeymoon. It was an awesome trip on the nice island. I highly recommend Wind City Travel, had an amazing experience. read more

We loved working with Kathy to plan our honeymoon to Paris and Amsterdam. It was the first time we had worked with a travel agent and we were referred by a family friend. Kathy was really helpful and we have already referred other friends to her for international trips they are planning. We can't wait to work with Kathy again to plan our next international trip! It took so much of the burden off planning!! read more

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 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! read more

It was so convenient to just call to call windy city travel and have Paula take care of everything...flight, hotel, and rental car. The only thing I had to concern myself with is what to pack. read more

We contacted Windy City Travel to help us plan three weeks with our 12 and 15 year-old grandchildren. Lynn and her team were great. In spite of the challenges presented by planning travel during the Covid pandemic and last minute travel restrictions imposed by some states, they put together a terrific plan that included a number of spots that were fun and entertaining for all of us. They thought of details and had suggestions we would have never thought of that really added to our enjoyment. The kids both commented on how much fun they had, not an easy accomplishment with teenagers, and we have memories we'll all share forever. We are already planning 2021 and can't wait to work with Lynn and Windy City Travel in, hopefully, more normal times. read more

I have worked with Kathy on a couple of different itineraries over the years and I wouldn't want to work with anyone else. She is very knowledgeable about Italy and she has also assisted us with a land/cruise trip to Spain & Portugal. Kathy's attention to detail is superb and her patience is unlimited. read more

We decided to use Windy City to help us book rooms and airfare for us and our guests for our destination wedding in Punta Cana. Initially it felt like they were over-quoting us as we found cheaper rates right through Apple Vacations but after they realized that we did our homework on rates, the rates were comparable. Our flights also got changed a few weeks beforehand and although they sent a letter informing us of our new itinerary, it wasn't great to know that our 1 hour layover got changed to 6 hours. Another thing is that since my name is Kathy and there is also a Kathy at Windy City, Janet keeps incorrectly sending me emails about clients. Although I have responded back to her saying that she sent them to me in error, I continue to get them. read more

I am giving Windy City Travel 1 star because of their follow up. They obviously did not want our business nor received it. After working with an individual there on our honeymoon to the Caribbeans and coming close to a decision they just fell of the face of the earth. Never responded to my emails. I ended up just working with another agency and have yet to receive any response back. read more

I am writing this review based on my husband Kyle and I's honeymoon in Thailand. We worked with Kathy A. at Windy City Travel and could not be more pleased with how our trip went. We had originally tried to plan the trip on our own, but with neither of us having traveled farther than the Caribbean we didn't know where to start. Kathy was our lifeline. My husband worked closely with her to find the best resorts and the best excursions for our trip. We ended up going for 10 days and we travelled to three different cities (Bangkok, Chiang Mai, and Krabi). Our hotels were wonderful and fit perfectly within our budget. We had trips planned to see the country almost every single day (temple tours, elephant sanctuary, cooking class) and we loved it. We truly felt that we got to experience not only the cultural side of Thailand, but also the beautiful beaches/islands of it as well. Couldn't recommend working with the Windy City Travel team enough, they made sure our Honeymoon was amazing! read more

I have been using Windy City and Janet since 2006 when she recommended a resort for my destination wedding and booked over 20 people for flights and for the resort. The experience was so pain free that I have been back twice since. First, Janet booked a honeymoon for me to the Dominican Republic and most recently to Couples Negril in Jamaica. On both trips Windy City made special requests to obtain for us the best possible rooms, and in each attempt, they were succesful. For our last trip to Jamaica I was pleasantly surprised that Janet managed to get us a $175 spa credit and a $75 gift shop credit. Another couple we were there with who went through a different travel agent did not get this deal. I will also add that Janet always books us on non stop flights to our destinations which is a huge bonus. In sum, I have always recieved prompt and courteous service from Windy City, and would not hesitate to recommend them to family and friends. read more

Being the cheapest person you ever want to meet, I actually got quotes from 3 travel agencies for my Trip to Italy and Greece to see who would get me the best deal. By a long shot, Marcie Allison at Windy City Travel was the least expensive. Furthermore, the hotels that they booked were higher rated and better reviewed than the other 2 agencies. The trip went great, Marcie is very service oriented, and I would definitely book through Windy City and use Marcie again! read more

I sent an inquiry for a European trip and got a phone call back from one of their agents. I had a nice, somewhat long and in-depth, call which ended with a promise of a return call with a loose itinerary of my future trip. I never heard back from this agent. I found this to be very frustrating because she took my time and promised a return call which I never received. I would not recommend this agent for that reason. I ended up booking my trip online at tripmasters and had a perfect vacation. I only wish I wouldn't have wasted time booking the trip waiting for a response from Windy City travel. read more

Kathy made my trip to Tahiti wonderful. She made sure our flights, connections, and transfers were timely and great quality. I was hesitant with booking this trip myself being such an expensive trip but after Kathy appraised my package it was actually cheaper. I would definitely use Windy City Travel again. Thank You Kathy for your help on booking our wonderful trip. read more

WOW..our honeymoon was amazing!! Planning a wedding can definitely be hectic so I decided to reach out to travel agent to help out with the honeymoon. Kathy was AWESOME to work with! Kathy listened to every place in Europe that we wanted to visit from Florence to Positano to Mykonos to Santorini and made it all happen. She planned transportation, great hotels, and excursions for us and worked within our given budget. She was very responsive and answered emails and returned calls very quickly. Mu husband and I will definitely being using Kathy for future vacation trips :) read more

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 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! read more

My husband I and pulled the trigger on a warm weather getaway with about a month lead time...we needed some professional help getting the travel arranged! I called Windy City Travel after they popped up on a quick Google search. Kathy was "assigned" to help us plan out trip and she couldn't have been more helpful. She was quick to respond to emails and return phonecalls (which was much appreciated due the lack of time we had in planning!). Kathy recommended several destinations and made sure our request to stay at or under budget didn't get dismissed. Overall, it was mission accomplished...we had sun, ocean, pool and cocktails for a reasonable price. She even went out of her way to reserve us seats on a booked leg of our travel, and made sure she walked us through our arrival into Jamaica and the logistics of getting to and from our hotel. Two thumbs up for Kathy at Windy City! read more

Highly recommend booking with Kathy! She planned us an amazing Greece honeymoon! She was very helpful throughout the entire process. The whole trip was well planned out and allowed us to really just enjoy it all. Highly recommend using Kathy for any trip!!! read more

I'm really bummed to write a negative review for this place but at this point I feel that it's unavoidable. I have now tried to work with two different agents at this company. The first agent flat out refused to work with me via email and completely ignored me after contacting me after I filled out information online. It just so happened that they went on vacation and someone else filled in for them who I thought was going to be great. We received a quote and some details about what we were looking for and decided that it wasn't going to work so we were going to proceed with the one place instead of the two options that would have had us flying a ton. This was on December 16th. It is now almost the beginning of February and we have yet to receive an updated proposal for the one place. We weren't told they were going to be out of office for two weeks on vacation, never set up an out of office I only knew because I called and received their voicemail. When I reached out again this past week when I knew they were back in office, they tried to tell me they sent a revised proposal and followed up twice which is not the case. I can't find their emails in my spam or junk or inbox. I'm just frustrated, this was for our honeymoon and we have to start booking soon. Needless to say we will be taking our business elsewhere. read more