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.

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

Start Planning

Call us at (312) 951-0710 or fill out the short form below to start planning your next experience.

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windy city travel chicago
Windy City Travel
a division of H&S Travel Group, Inc