Windy City Tour Company

Trails and Tours

We partner with Chicago's leading experts on wine trails and brewery tours around the Midwest - Evanston Cellars - to offer you tours of the wineries, breweries, and vineyards around the Chicago area.

We offer seven different and unique beverage experiences which can include wine, beer, and distilled spirits.
Each tour has its own character and charm.  We like to be both entertaining as well as educational.
Ask us which one is best for your group!
  • Lake Michigan Shore Winery and Vineyard Trail (SW Michigan)
  • Duneland Tasting Room Trail (NW Indiana)
  • Fox Valley Tasting Room Trail (Illinois)
  • Grain, Grape & Still Trails (wine, beer, and spirits tasting all in one trip) (We have three different GG&S trails!)
  • South Loop Chicago Craft Beer Trail
  • North Loop Chicago Craft Beer Trail
On all our tours, we include a picnic lunch or stop at a favorite restaurant to provide for a complete wine experience.

Our prices range from $99 to $185 per person for the day depending on the level of service and the number of guests that will be in your party.  

By using the BOOK NOW buttons found on this web site, you can view our calendar and schedule a tour.

If you are making arrangements for a larger group, you can call us directly at 847.902.0733 or use the contact form on this web site to let us know how we can help you plan a memorable group outing.  Depending on the number of people you will be hosting, we can offer your group a discount from the normal rate.
Please allow for a full day on all the wine tours due to the distances involved in driving out to the wineries and vineyards.

Our brewery trails take approximately four - five hours including time for the lunch that is included in the tour fee.
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