May Kicks Off Chicago Festival Season. Here Are Food Events to Get You Started This Month

Summer’s on the horizon, Chicago, and with it comes the return of festival season. From now through fall, we’ll be spotlighting food-focused street fests and other events that celebrate the city’s and suburbs’ diverse food scene. To get things started, here’s a handful of May festivals to get your appetite ready for the months ahead.

Are we missing an event? Submit it for consideration to [email protected] 

Jeff Mauro Live: From Clown to King

Friday, May 1 and Friday, May 29 | City Winery
Chicagoan, Food Network host, and “Sandwich King” Jeff Mauro hosts this blend of food, comedy, music, and storytelling at City Winery.

Naperville Food Truck Festival

Saturday, May 9 | Naper Settlement, Naperville
Naperville’s celebration of food trucks returns this May with more than 20 food trucks, with everything from lobster rolls to Italian street food. 

Evanston Arts & Craft Beverage Crawl

Thursday, May 14 | Dempster Street, Main Street, Chicago Avenue in Evanston 
This combination arts-and-beverage festival in Evanston takes place in the Dempster Mile commercial district. Sip on craft drinks while you peruse the pop-up art galleries in shops along Dempster Street, Main Street, and Chicago Avenue.

Aurora Food Truck Fest

Friday, May 15 | On Benton Street from River Street to Broadway, Aurora
Aurora’s spring food truck festival returns this year with plenty of food trucks representing a variety of cuisines, plus music and entertainment. 

Long Grove Chocolate Festival

Friday, May 15 through Sunday, May 17 | Downtown Business District, Long Grove
This long-running chocolate festival returns to downtown Long Grove, with a wide array of chocolate vendors, family-friendly activities, music, and chocolate-themed activities and games.

Chicago Food Truck Fest

Fridays, May 15, 22, and 29 | Daley Plaza, 50 W. Washington St. 
On Fridays and select Wednesdays starting May 15 through early October, the city hosts a rotating selection of food trucks in Daley Plaza. 

Ballpark Brews Fest

Saturday, May 16 | Wintrust Field, Schaumburg 
Some 50 breweries and 100 different beers come to Wintrust Field in Schaumburg for this 13th annual festival of brews.

Rhubarb Festival

Sunday, May 17 | Kankakee County Museum, Kankakee
The Kankakee County Museum hosts this celebration of rhubarb each year, which features pies, jams, music, kids’ activities, and more.

Blues, Brews, and BBQ Fest

Saturday, May 23 | The Forge, Lemont Quarries 
Chicago brews meet Chicago blues plus flavorful BBQ at this festival at the adventure park in Lemont.

Mayfestiversary

Saturday, May 23 and Sunday, May 24 | Ravenswood Ave. and Belle Plaine Ave.
Mayfestiversary, hosted by Begyle and Dovetail breweries, returns to Ravenswood with this annual spring block party that doubles as a fundraiser for the Friendship Center, a local food pantry.

Windy City Hot Dog Fest

Friday, May 29 through Sunday, May 31 | 4000 N. Milwaukee Ave.
This celebration of one of Chicago’s iconic foods returns for its fifth year and features a competition for Best Frankfurter.