Frequestly Asked Questions

You have questions? We have answers!

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

A: For 2019, our fees for a private tour are $185/person.  If you take your tour on a Sunday or a weekday, we offer a 10% discount to this price.  Groups of 20 or more may also qualify for a 10% discount (depending on your requirements). 


We include round trip transportation from a location within the Chicago area (including suburbs), visits to three wineries or breweries (including tasting fees), a gourmet lunch, bottled waters and snacks on board, and a departure toast to get the trip started right!

Q: What do you charge for open "join in" tours that are not private?

A: We no longer offer "join in" tours unless the first booking meets a four person minimum.  Our tours are group tours with set minimums that vary from four to eight people depending on the tour you wish to take.

Q: How long is a tour?

A: Our vineyard and tasting room tours take approximately 6 - 8 hours.  We will leave your departure location between 9 - 10 am (depending on departure location) and try to arrive back by 6 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.  Larger parties (10 or over) tend to take more time at each stop.

Our West Loop Wine Trail tour 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.  Please note that this trail is a walking tour with a total walking distance of approximately 1 mile total.

Brewery tours are about 3-4 hours depending on the day of the week and the time of day.  Also, if our guests are having fun and we don't have another tour after, we allow our guests to stretch out their time a bit!


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

A: Our company van holds up to 11 guests (if one guest is willing to sit next to the driver).  We can also take groups larger than 11 but to we need a final number before giving you a fixed bid since we would either rent a larger vehicle or contract with an outside vendor to provide a mini-coach (for 16-23 guests) or a full coach (24-53 guests).

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 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: We do not hold any dates until we receive a 50% deposit with the remainder due on the day of the tour after the tour is completed. We can create an online booking platform for you if you would like your guests to pay individually, but you will have to meet our minimum guest requirements for us to hold the date.  This online booking platform is serviced by and we create a special password for your group if you choose to have each guest sign up individually.

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 or Evanston Cellars 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 an avid 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 tours do you offer?

A: In addition to our wine tours, we also offer tours of craft breweries and distilleries around Chicago.

All our tours feature three tastings and a meal along the way.

Q: Do you offer non alcohol tours suitable for families and young children?

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.  We are members of the Chicago Tour Professionals Association and lead tours of sights of interest around Chicago when requested.


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

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




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