About Us

We are a boutique tour operator specializing in tours around Chicago that are hard to do without a guide and transportation. Operating in a ten-passenger air-conditioned van, we offer tours that are both informational and entertaining. We specialize in tours of wineries and breweries around Chicago but now also offer tours such as Route 66: America's Highway, Chicago South Side Highlights, The Pullman National Historic District, and Michael Jackson and NW Indiana.

Why book with Us

We are experts at operating tours that feature Midwest wine and beer, and points of interest between Chicago and Indiana. We have a vast knowledge of the area gained by living in the area and researching the extensive history of our city. We are also vintners and work in the industry so can answer any questions regarding the process of wine making.

Tours and Holidays by Windy City Tour Company

Windy City Tour Company has not yet published any tours.