Travel & Tours
Windy City Travel

Travel & Tours

Windy City Travel

About Windy City Travel

Discover Windy City Travel, a top-rated Travel Agency in N Wells St, 1357 N Wells St, known for helping customers create memorable travel experiences. Backed by 4.80 stars and 194 reviews, we’re proud to offer great service and quality and attentive service every step of the way.

★★★★★ 4.80 rating (194 reviews)
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Expert Guides

Local knowledge & insight

Flexible Booking

Easy changes & cancellation

Safe Travel

Your security is priority

Personal Touch

Customized experiences

Travel Experiences

Guided Tours

Expert-led adventures to the world's most captivating destinations.

Accommodation

Handpicked hotels and unique stays that match your style and budget.

Custom Itineraries

Personalized travel plans designed around your interests and dreams.

Windy City Travel

Your Journey Starts Here

From planning to return, we're with you every step of the way to ensure your adventure exceeds expectations.

4.80
Star Rating
194+
Happy Travelers

Traveler Reviews

Stories from our adventurers

Debra Farrell

Debra Farrell

a year ago

Peru - March 2025 We recently visited Peru with Windy City Travel in partnership with WBBM and had an exceptional experience! We traveled through Lima, Sacred Valley/Cusco and Machu Picchu. The planning and execution of the trip was done in a very efficient manner utilizing all local modes of transportation. The selection of lodging, meals and planned excursions was excellent and service was great in all locations! Knowledge of the areas and attention to detail enhanced the success of the trip. We highly recommend using Windy City Travel for your next adventure!

Pedro Birman

Pedro Birman

a year ago

Windy City did a really good job planning my vacation to Morocco. Deni, our point of contact, did a good job of leveraging his local resources and we were always treated with the upmost care during our trip. We didn’t think our stay at the La Mamounia could ever be matched, but Windy City’s suggestion to stay at the Kasbah Tamadot at the end of the trip was amazing! Our local guide and driver were always going over and beyond our expectations as well.

Jill

Jill

a year ago

I cannot say enough great things about Kathy with Windy City Travel! Kathy was so attentive to our requests and responsive throughout the entire process. Our trip to Iceland and Sweden (Oct/Nov 2024) would not have been what it was without her!

Ryan Larson

Ryan Larson

2 years ago

Kathy A. at Windy City Travel is simply amazing! She has helped our family plan trips from Italy to Greece, Spain and Portugal, Egypt and everything in between. Kathy is knowledgeable, responsive, spot on, gets things done, and leaves no details behind. Thank you for everything, Kathy!

Nicoline Shoffer

Nicoline Shoffer

5 months ago

I will never use any other travel agent!! Cassie Thome is an absolute delight to work with. Our family trip to Paris was seamlessly planned. Cassie had amazing recommendations not only for hotels in our price range, but also catered to our interests and personalities. This is a tall order when trying to make a trip fun for educators and their teenage son! Cassie had lots of recommendations on how to not only see all the regular tourist sites, but also special interest tours and activities that were happening during our stay. We had an absolute blast and made so many wonderful family memories.

Sherry McAllister

Sherry McAllister

Edited a year ago

ICELAND September 2024 Our 10 day trip to Iceland in early fall was great! We are grateful for all the hotel selections, sight recommendations, assistance with dinner reservations and adventurous excursions suggested by our travel agent at Windy City Travel. Iceland has such a diverse topography. We took our time, rented a car and explored volcanoes by foot and air, trekked glaciers, viewed numerous waterfalls from many viewpoints and even snorkeled the chilly waters of the Continental Divide. Words cannot begin to describe the beauty and adventure of this island. If relaxation sounds appealing to you, stay at The Retreat (5 stars) and stay in your bathrobe and slippers all day and enjoy fabulous Icelandic cuisine in the evening. Iceland has a magical charm, not to be missed! We will be calling Kathy again to help us plan our next destination! MOROCCO April 2024 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.

Lorne Cohen

Lorne Cohen

4 months ago

As new clients of Kathy Allinson at Windy City Travel, our recent vacation in Australia was one of the best we have ever taken. She flawlessly arranged and coordinated 8 flights, 8 hotels, a rental car and numerous excursions/activities for us. She's personable, knowledgeable, very responsive and took the time to learn about us and our interests. We will be partnering with her from now on.

Dylan Glaser

Dylan Glaser

7 months ago

I’ve worked directly with Karen, she’s amazing! Very patient and understanding. Also very helpful with our needs. She helped me book an amazing trip for my parents and most recently helped me with our trip to Mexico. Always attentive and there for you if you have questions or issue. Gives you the best advice on where to go what to do and what to avoid. Highly recommend Karen and Windy City travel. You will not be disappointed. I found Karen through a friend. My last travel agent just wasn’t cutting it for me and Karen has been nothing short of amazing. So thankful for her. We’ll be back very soon

MJ L

MJ L

2 months ago

We had an excellent experience with Dana C. who helped me plan a trip of a lifetime to Costa Rica (Guanacaste -Cala Luna resort) with my mom, an older adult. From start to finish, Dana was prompt and trustworthy in her guidance and responses. For example, we took a direct flight and it was only 4.5 hours to paradise. I’d work with her again any day. Highly recommend.

Tamara Vokes

Tamara Vokes

a month ago

Our agent, Kathy Allinson, was great. She organized our trip to New Zealand perfectly and everything functioned like clockwork. There were some activities that we would not have chosen ourselves but were glad that we had a chance to experience them. This was a truly marvelous trip and we’re grateful to Kathy for having arranged it.

Frequently Asked Questions

Common questions about Windy City Travel

Business Features

Highlights & Amenities

From the business

  • Identifies as women-owned

Service options

  • Online appointments
  • On-site services
  • Language assistance

Crowd

  • LGBTQ+ friendly

Payments

  • Credit cards
  • Debit cards

Start Your Adventure

Let's plan something amazing together. Reach out and tell us about your dream trip.

Office

1357 N Wells St, Chicago, IL 60610, United States

Hours

Open Now · Thursday 9 AM-5 PM
Thursday 9 AM-5 PM
Friday 9 AM-5 PM
Saturday 9 AM-5 PM
Sunday Closed
Monday 9 AM-5 PM
Tuesday 9 AM-5 PM
Wednesday 9 AM-5 PM
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