About Windy City Travel

Windy City Travel has been in business in Chicago as a full-service travel agency in Old Town since 1981. Our team of travel specialists are renowned for providing personalized service for all your corporate and leisure travel needs – including, destination weddings, honeymoons, vacations, family reunions, groups and incentives. Our corporate agents are veterans at corporate travel and our leisure agents have traveled the globe and are able to provide information, details and suggestions to truly tailor a vacation, wedding or honeymoon to meet your needs and preferences.

You will receive 5-star treatment throughout the entire process! Our experienced travel specialists have a passion for travel so will bend over backwards to customize every detail of your trip and ensure you have the trip of a lifetime again and again. The bedrock of our business is putting service first. In a business that is all about the deal and brand loyalty is practically non-existent, we couldn’t be prouder of the fact that 2/3rds of our business every month is from repeat and referral customers.

When working with us you will soon learn that we have a deep love of travel. Our travel specialists have expertise in different areas of the world. So, we will match you up with the best fit based on where you are looking to travel.

We look forward to planning your next adventure.

windy city travel

Contact Us

  • Our vacation specialists have stayed at or visited many of the resorts we recommend (unlike most online agencies). In order to best match your requirements with the array of resorts, packages and options available, we believe it is best for you to allow us to respond by speaking with you personally by phone about your contact request.
  • This field is for validation purposes and should be left unchanged.