Windy City Wine Festival Food & Drink Event / Food Festival / Wine Festival Every year in September

Chicago was once the center of the fight against prohibition. Today, the wine flows freely in the Windy City as Chicago celebrates its right to imbibe. Every year since 2005, over 10,000 oenophiles from around the world come to Chicago to sample over 345 wines at the Windy City Wine Festival.

On the second Friday and Saturday of September, the tents and booths around Buckingham Fountain in Grant Park welcome new and experienced wine drinkers to discover favorite wines from both national and international wineries. With wine seminars, a beer-tasting garden, cooking demonstrations, and food from the best restaurants and caterers in Chicago, the Windy City Wine Festival has something to satisfy everybody’s appetite.

Tickets to the Windy City Wine Festival in Chicago are around $10 for designated driver tickets and around $35 for wine tasting tickets, which include ten tastings and a souvenir wine glass.

Some of the profits from the Windy City Wine Festival will go to the Grant Park Conservancy and guests under 21 are free when accompanied by a paying adult. After sampling the food and local music, dance off all that wine at the clubs surrounding Grant Park.