Frequestly Asked Questions

Thank you for inquiring about our Wine and Beer tours in the Chicago Area and Harbor Country in SW Michigan!

Please note that due to the COVID 19 Pandemic, we are limiting our tours to small private groups.


We are frequently asked questions regarding booking one of our tours.  


Q: What do you charge for a private tour and what does that fee include?

A: For 2020, our fees for a private tour are $195/person.  We include round trip transportation from a location within the Chicago area (including suburbs), visits to three wineries or breweries (including tasting fees), a wonderful lunch with cocktail at JOURNEYMAN Distillery, bottled waters on board, and a departure toast to get the trip started right!

Q: That price seems quite high.  What do we get for that?

A: All the wineries in SW MI have raised their tasting fee prices.  In addition, we are only booking smaller groups so we no longer have the luxury of adding revenues by increasing guests.  For that reason we have made a slight increase to our pricing for 2020.


Q: Due to the Covid 19 Pandemic, how have you changed how you operate?

A: We drive with windows down to keep circulating the air, we require face masks when entering each winery and lunch stop, and we encourage our guests to use hand sanitizer frequently.  We are also operating our tours to be private with a maximum guest count of 10.


Q: How long is a tour?

A: Our vineyard and tasting room tours take approximately 6-8 hours.  We will leave your departure location at 11 am (downtown Chicago) and try to arrive back by 7 pm so that you can continue your celebration in the evening if you so desire. Times have to be flexible due to traffic and construction but we are able to hold to these hours on most of our trips.

Our West Loop Wine Trail tour (launched in 2017) is about three hours long and is designed for a shorter experience and a more varied selection of food items through shared small plate servings.


Q: How many people can we take on our tour?

A: For the summer of 2020, we are limiting our tours to a minimum of 4 to a maximum of 10 depending on which tour you sign up for and what vehicles we have available for the requested date.

Q: Will you pick up and drop off our group at a location of our choice?

A: Yes, for most private tours that originate within the City of Chicago, we will pick up and drop off your group for no additional charge.  If your tour originates outside of Chicago, there is an additional one time charge of $100 to cover gas and the additional time it takes for our driver to start at your location.


Q: Which tour would you recommend that we take?

A: It really depends on the type of experience you would like to have.  During the summer, our most popular destination is SW Michigan (about an hour and 1/2 away from the Magnificent Mile).  We also have tours that visit tasting rooms in NW Indiana, Fox River Valley (west of Chicago), and a walking tour of tasting rooms in the West Loop area of downtown Chicago.  Please call us to discuss which tour is best for you and your guests.


Q: Where do you stop for lunch?

A: We have pre-selected several wonderful restaurants that serve fantastic and tasty meals and also have menus that cater to those with dietary restrictions (gluten-free, vegetarian, nut allergies, etc). We will make sure that your party eats well between your wine tastings.  Once you book your tour, based on the day of your trip and the size of your group, we will give you both restaurant and menu options that you can choose from.

Q: One the guests on the tour is pregnant. Can you discount the ticket price?

A:  Yes, if you or someone in your party is not participating in the wine or beer tastings, we will discount those fees from the overall price in the form of a cash rebate on the day of the tour.


Q: Can we bring a cooler and drink wine on the bus?

A: Yes,you can bring a cooler on the bus and depending on how the day is going, you may be able to have some wine on the bus.  We discourage heavy drinking - the purpose is to have fun, enjoy the day, and come home safely.  For that reason, we reserve the right to limit the consumption of alcoholic beverages to only the four stops that are built into the tour if it is necessary for safety reasons.


Q: How do I reserve my tour?

A: Our online booking platform is serviced by and we encourage you to purchase your tickets through this platform.  We can also send you a digital invoice using SQUARE.


Q: Do you have any customer reviews and where can I see photos of previous tours?

A: We have been operating wine tours for over five years and we keep an archive of previous tours on our Facebook Albums area.  Visit either Windy City Tour Company on Facebook and you will see many previous tours and can read reviews.  We are also reviewed favorably on Trip Advisor and YELP.


Q: Can we pick the wineries we visit?

A: We do take requests and try to work with you when at all possible, but in general, we have some favorite spots that we visit on our tours for a variety of reasons. The most important reason we choose the wineries we do is that we feel the wine you are being served is better than other alternatives and that the tasting room staff is better trained to answer the questions you may have about what you are trying.


Q: What makes you the best choice for leading a wine tour?

A: I am a home wine maker and am active in several industry groups around the Midwest including the Michigan Wine Council and the Illinois Grape Growers and Vintners Association. I also own a private label wine brand (FORTY WINKS) that is available in over 20 retailers around the Chicago area.


Q: What other beverage tours do you offer?

A: In addition to our wine tours, we also offer tours of craft breweries and distilleries around Chicago. We even have a tour that visits a distillery, a brewery, and a wine tasting with lunch! All our tours feature three tastings and a meal along the way.

Q: Do you offer other types of tours?

A: Yes in addition to the wine and beer tours we are best known for, we offer several tours of historical interest as well as tours that appeal to those that want explore that natural wonders in and around Chicago.  I am a member of the Chicago Professional Guide Association and also do city tours when hired by groups to do that.


Q: If I have other questions, what is the best way to reach you?

A: You can contact me using our web site ( or call me at 847.902.0733.


Thanks again for your interest in taking a wine tour with us!