Skip to main content

Summer is Almost Here, and Festival Season is Upon Us. Here are Food Events in Chicago This May

Meredith Francis
An aerial view of a crowd at a street festival
Mayfestiversary returns to Ravenswood this May. Credit: Steph Byce / Mayfestiversary

Get more recipes, food news, and stories by signing up for our Deep Dish newsletter.

The sun is shining in Chicago again, and another bustling summer full of festivals has arrived. Below are some food-centric events that offer a chance to get out and enjoy the city and the warm weather. As always, be sure to double check the event pages for updates to times, locations, and ticket prices.

Do you know of an upcoming food event? We could feature it in our monthly round-up and in our Deep Dish newsletter. Send tips to [email protected]!

Cinco de May at Time Out Market

Wednesday, May 1 through Sunday, May 5 | Time Out Market, 916 W Fulton Market
Time Out Market Chicago is having a several-day-long celebration of Cinco de Mayo, with taco and margarita specials, tequila tastings, and more.

Naperville Food Truck Festival

Saturday, May 4 | Naper Settlement, Naperville
Naperville’s celebration of food trucks returns this May with more than two dozen food trucks, along with live entertainment, activities for the kids, and a Cinco de Mayo beer garden for the grown-ups.

Evanston Arts and Craft Beverage Crawl

Thursday, May 16 | Various Locations, Evanston
This event combines a celebration of local artists with the taste of craft beverages. Attendees have the option of two different routes that will take them on a crawl with various stops along the Main-Dempster Mile in Evanston.

Long Grove Chocolate Festival

Friday, May 17 through Sunday, May 19 | Downtown Long Grove, 145 Old McHenry Rd.
This popular chocolate festival returns to downtown Long Grove this May, with a wide array of chocolate vendors, family-friendly activities, music, and chocolate-themed activities and games.

Rhubarb Festival

Sunday, May 19 | Kankakee County Museum, 801 S. 8th Ave.
The Kankakee County Museum hosts this celebration of rhubarb each year, which features pies, jams, music, kids' activities, and more.

Mole de Mayo Festival

Friday, May 24 through Sunday, May 26 | 18th St., between Ashland Ave. and Blue Island Ave.
This festival in Pilsen shows off regional and specialty mole dishes from restaurants in and around the neighborhood. The festival also has music, art, cultural performances, and a market.


Saturday, May 25 and Sunday, May 26 | Ravenswood Ave. and Belle Plaine Ave.
Two popular breweries on Malt Row, Begyle and Dovetail, come together for this annual spring block party that doubles as a fundraiser for the Friendship Center.

Randolph Street Market Festival

Saturday, May 25 and Sunday, May 26 | 1341 W. Randolph St.
The Randolph Street Market is back for its 21st season with vintage fashion, furniture, and crafts. This year, the festival says it will have an expanded food court and cocktails, too.