Wine Trails

Discover the world of Midwest Wines!


Midwest wines are an undiscovered treasure and we are Chicago’s experts in finding the hidden gems that are part of the active wine industry here in the Midwest.


We choose from among the best vineyards and wineries in Illinois, Indiana and Southwest Michigan to introduce you to the quality and variety of wines from the region.

Please note that all our tours are private tours.  We will pick you up at one location and drop you off at the same location unless a different arrangement is agree upon when booking.


On all our tours, we visit three wineries or tasting rooms and include lunch or shared plates to provide for a complete meal during your personalized wine experience. 


Most of our wine trail tours take the entire day so when reserving your tour, please plan accordingly. 


Due to the distances involved in driving out to the tasting rooms, wineries and vineyards, construction and weekend traffic patterns, we ask that you allow between 6-8 hours when booking your tour.


By using the PEEK booking 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 or the day of your event, we may be able to offer your group a 10% discount from the normal private tour rate.



We'll make your visit to Chicago and Midwest Wine Country a day to remember!