Windy City Travel - A Chicago Travel Agency

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 Old Town, Chicago since 1981. The staff is renowned for providing personalized service for all your corporate and leisure travel needs including group travel, vacations & cruises, honeymoons, and destination weddings. Our corporate agents are veterans at corporate travel and our leisure agents have traveled the globe and are able to provide information and suggestions to truly tailor a vacation, wedding, or group 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 and cruise options. Our preferred relationships will be available to you with value-added amenities and supplier discounts.

WHY US?

Knowledge

Convenience

Problem Solving

Savings

Supplier Relationships

Loading...

“Kathy did an outstanding job planning our trip to Scotland and Ireland. Everything was organized for us and we didn’t have to worry about a thing. She is very knowledgeable in locations and well organized in planning out the day to day activities for you. We never felt like we were on a strict schedule, but we never had to think about what to do next. I can’t wait to use her again for our next adventure. Thank you!”

Anita Clapham
"Kathy is great! Each time I use Windy City, I am provided with excellent service, information about cities, places to go and awesome accommodations. I know that we live in a "Do it yourself" age for travel, but I love using Windy City! Australia was great.”

Leeandra Khan
Lynn helped me book an annual corporate trip for 45 people to Cancun. She went above and beyond to assist with flights, hotels, transfers and other reservations. I can't thank her enough for her professionalism, expertise and efforts to ensure our trip was a success. We will definitely call her next year and for personal travel as well!”

Nicole Gariti

Where would you like to go?

Africa

Asia

Australia & New Zealand

Caribbean

Europe

North/Central/South America

What type of trip are you planning?

Land Vacations

Escorted Tours & Safaris, Beach Vacations, All Inclusives

Cruises

River and Oceanic. Europe, Alaska, Caribbean

Groups

Family & Friends, Business Meetings & Conferences, Destination Weddings

Give yourself permission