Tours and Trails

From wineries in the tranquil Midwest countryside to the urban experience of craft breweries and artisanal distilleries, Windy City Tour Company can take you there.


We are Chicagoland's premiere tour company for personalized small group tours of wineries and wine tasting rooms around the area.  

If you are traveling to Chicago and are looking for a fun way to explore it, you've come to the right place. 

If you live here and are looking for a new way to enjoy the Windy City, or want to entertain guests, we can help you with that too.  


Explore our Wine or Craft Beer options. We can also arrange distillery tours if you want to learn about the intriguing world of artisanal world of craft spirits.  

We specialize in private tours for events such as bachelor or bachelorette parties, family reunions, birthday parties, and corporate events.  We can create a very special day for you and your guests!


With our contacts in the wine and grape growing industry around the Midwest, we can also create a very special ecotourism experience that includes trips to overnight destinations such as Saugatuck, (MI), Traverse City (MI), and Ottawa (IL).  These trips include tastings, room bookings, and special culinary meals at gourmet restaurants.  Call us at 847 902 0733 for more information on these special offerings!

We look forward to meeting you!