Today we’d like to introduce you to Dileep Gangolli.
Dileep, let’s start with your story. We’d love to hear how you got started and how the journey has been so far.
Windy City Tour Company was launched in 2013 to introduce customers to wineries and craft breweries in the Chicago area. Being a hobby wine maker and home brewer, my interest led me to explore viticulture and agriculture in the Midwest and I was pleasantly surprised with how much activity was going on right in our back yard!
Illinois has over 100 wineries, Michigan has close to 200, and Indiana has about 100. Wineries in the Midwest use grapes that are unique to the Midwest and that have been cultivated to withstand the harsh, cold winters that we experience here. That makes for wines that are not made or even available in better known areas such as California or Europe.
While attending the state conferences for vintners and grape growers in Illinois, Indiana, and Michigan, I made friends with many of the winery owners and developed a robust network of talented people dedicated to making great wines that deserved to be enjoyed by more people.
Windy City Tour Company became the first travel company to focus on taking Chicago residents and visitors to these wonderful wineries and tasting rooms just beyond the Chicago area. We currently offer five wine trails and visit SW Michigan, NW Indiana, the Fox River, Saugatuck, and Utica. In addition we have just launched a West Loop Walking Wine Trail who want a fun experience but don’t have a whole day to spend in wine country.
We also offer several Craft Brewery tours as well including a South Loop and North Loop Trail. Often clients have breweries that they want to visit and we do our best to include those if they have a preference.
We include tasting fees and food options with all out tours. Round trip transportation is also part of the package and we can accommodate all sizes of groups and specialize in corporate events.
We are pleased that customers recognize that we provide a unique experience at price points that represent good value. We look forward to meeting readers of Voyage Chicago and if they want more information on our tours they can visit www.windycitytourcompany.net.
Overall, has it been relatively smooth? If not, what were some of the struggles along the way?
Like any small business, we have had challenges that we have had to overcome. While we were able to get customers right after starting, figuring out how to market our services to customers and figuring out the proper price points took some time to figure out. We do no advertising and depend on SEO, word of mouth, and customer referrals for our business.
When we started the Great Recession was still on everyone’s mind and getting access to capital was impossible. I had to dip into retirement savings to fund our businesses including buying our tour van and printing rack cards and brochures.
In the same year, we also started a wine distribution business (Evanston Cellars) that focused on selling wine made in Michigan under our own private label. I needed capital to build inventory and then had to turn it over as fast as I could. That has been a real challenge. Vendors, while open to local beer and spirits, are still resistant to wine made locally but I have been successful in getting slotted at about 25 retailers around Chicago. Once we get in, our wines do very well since they are good value and quite different from other options in their price range.
Please tell us about Windy City Tour Company.
Windy City Tour Company is the only Chicago tour company that focuses on wine and beer tours that are led by an experienced wine maker. I am active in many trade groups related to wine, agriculture, and tourism and bring my experience to the tours that we offer.
I am most proud of the reviews our tours get from our customers. They always have a good time and enjoy the wineries and breweries we choose to visit. Safety is also a top concern for us and by taking our tours, clients get a designated driver while being able to enjoy the day with no worries about drinking and driving.
I gear the tours to the client. If they want to learn more about wine and the wine industry here in the Midwest, I will answer their questions and walk the vineyards with them to show them how the grapes are grown in the vineyard and wind up in their glass. If they just want to have a good time out in Wine Country, I can do that too and keep quiet! It’s up to them about how they want to shape their day.
We have vetted out the best restaurants to stop at on each of our tours so I am very proud that our clients always comment on how pleased they were with the meal we serve along the way. We offer several menus and choices on each tour and can accommodate all dietary restrictions.
Our guides take pictures along the way and post them to social media (with the permission of the clients) within 24 hours so that they can share them with family and friends if they want to.
We are a one stop shop for exploring wine and enjoying a day in Wine Country within two hours of Chicago!
If you had to go back in time and start over, would you have done anything differently?
Fortunately, I don’t think I would do much differently. I have been very careful in how I have operated the business balancing risk with reward.
I would like to explore how to expand the business locally by offering culinary and food tours as well as offer tours that explore the wonderful history that Chicago offers.
Pricing:
- $175/person all day wine tours (private and join in tours are offered) SW MI Wine Country
- $129/person West Loop Wine Trail
- $159/person Duneland Tasting Room Trail (NW Indiana)
- $159/person Fox River Valley Tasting Room Trail
- $99/person North Loop and South Loop Craft Brewery Tours
Contact Info:
- Address: 2113 N Kedzie Blvd, Unit C
Chicago IL 60647 - Website: www.windycitytourcompany.net
- Phone: 847.902.0733
- Email: dileep@windycitytourcompany.net
- Instagram: dileepgangolli
- Facebook: https://www.facebook.com/windycitytourcompany/
- Twitter: @evanstoncellars
- Yelp: https://www.yelp.com/biz/windy-city-tour-company-chicago-2
- Other: www.evanstoncellars.com

Image Credit:
Laura Hamm Photography
Getting in touch: VoyageChicago is built on recommendations from the community; it’s how we uncover hidden gems, so if you know someone who deserves recognition please let us know here.
