About Windy City Tour Company

Welcome to Windy City Tour Company.  



We are Chicago's experts on the wine trails around Chicago and other parts of the Midwest!  We now also offer tours to craft breweries and artisanal distilleries as well.

My name is Dileep Gangolli, and along with my wife Janice MacDonald, we operate Windy City Tour Company to share our love and passion of wine, beverages, and food with others that want to explore and learn about the wine and craft beer industry here in the Midwest.


I am an avid winemaker and have been making wine as a hobbyist for over ten years.  In 2013, we started our own wine brand, Forty Winks, and distribute our portfolio to restaurants and retailers around the Chicago area.  Our wines are made from grapes sourced in the Midwest.


Janice and I are both musicians and private music instructors during the academic year. Among the groups we perform with are the Chicago Sinfonietta, the Chicago Philharmonic, the Joffrey Ballet Orchestra, Broadway in Chicago, and the Lake Forest Symphony Orchestra.

The bulk of our wine and nature tour business is during the summer months (between Memorial Day and Labor Day), but our craft brewery and culinary options can be enjoyed all year round.


We specialize in working with clients to create an unforgettable private event that allows you and your guests to concentrate on having fun. Whether you are visiting Chicago or are a local planning a special event like a birthday or wedding party, we can arrange a private tour tailored to your specifications.  We specialize in anniversary and bachelorette parties!


To view some of the tours we have done in the past, visit the photo albums area in both our Facebook pages, Windy City Tour Company and Evanston Cellars. Please visit our tour descriptions on our online booking platform PEEK or call our office at 847.902.0733 to learn more about our offerings.