Festival Season is Back. Here Are 15 Food Events to Check Out in May

Meredith Francis
The Daley Plaza City Market pictured in 2019. Image: Shelly Bychowski / iStock
The Daley Plaza City Market returns on May 11. Image: Shelly Bychowski / iStock

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With warmer temperatures and sunnier skies, Chicago has come alive once more. That means festival season is back. Here are some food-related events to brighten up your spring. We’ve also listed some of the weekly farmers markets that get started in May. Be sure to double-check the event pages for times, locations, and admission information.

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1. Lincoln Square Farmers Market

Beginning Tuesday, May 2, 2023 | Lincoln and Leland Avenues
Every Tuesday and Thursday beginning May 2, the Lincoln Square Farmers Market returns to Lincoln and Leland Avenues, near the Western Brown Line station. The market runs from 7:00 am to noon on Tuesdays, and 3:00 pm to 7:00 pm on Thursdays.

2. Aurora Food Truck Festival

Friday, May 5, 2023 | Benton Avenue, Downtown Aurora
Aurora is hosting this food truck festival along Benton Avenue as part of its First Fridays event series. Lots of vendors will be on hand, including some with vegan and vegetarian options.

3. Cinco de Mayo Celebration at TimeOut Market

Friday, May 5, 2023 | TimeOut Market Chicago
Kick off Cinco de Mayo celebrations with this beverage event at TimeOut Market in Fulton Market. The event features live music and specialty cocktails, and you can learn a little something about tequila while you indulge.  

4. Green City Market West Loop

Beginning Saturday, May 6, 2023 | 115 S. Sangamon St.
Green City Market’s West Loop location returns in early May. The farmers market runs from 8:00 am to 1:00 pm every Saturday through November. (The Lincoln Park market opened in April.)

5. Division Street City Market

Beginning Saturday, May 6, 2023 | 100 W. Division St.
One of the City of Chicago’s farmers markets, Division Street City Market, kicks off in early May and runs through the end of October. Fresh fruits, vegetables, flowers, baked goods, plants, and more will be for sale.

6. Naperville Food Truck Festival

Saturday, May 6, 2023 | Naper Settlement
More than two dozen food trucks will be parked at the Naper Settlement for this festival in Naperville. There will also be plenty of kid-friendly entertainment, and a Cinco de Mayo beer garden for the grown-ups.

7. Chicago Latino Spirits Festival

Saturday, May 6, 2023 | The Logan Theater
As an ode to Cinco de Mayo weekend, Latino mixologists and winemakers will be serving up rum, tequila, mezcal pisco, and much more at this 21+ beverage festival at The Logan Theater.

8. Daley Plaza City Market

Beginning Thursday, May 11, 2023 | Daley Plaza
Another one of the city-sponsored farmers markets kicks off on Thursday, May 11 at Daley Plaza. Shop for produce and other treats under the Picasso sculpture every Thursday morning to early afternoon through the end of October.

9. Evanston Arts & Craft Beverage Crawl

Thursday, May 18, 2023 | Dempster Mile
This combination arts-and-beverage festival in Evanston takes place along 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.

10. Historic Downtown Long Grove Chocolate Festival

Friday, May 19 through Sunday, May 21 | Downtown Long Grove
Chocolate lovers, this one is for you. This festival returns to downtown Long Grove and features music, family-friendly activities, and, of course, chocolate. Lots of chocolate.

11. Margarita and Sangria Fest

Friday, May 19, 2023 | Lincoln Park Zoo
Sip on margaritas and sangria at this adults-only event at the Lincoln Park Zoo. Walk around the zoo’s gardens and animal exhibits without the crowds while you raise a glass (or two) to the zoo’s new lion cubs. Food will also be available for purchase.

12. Rhubarb Festival

Sunday, May 21, 2023 | Kankakee County Museum 
The Kankakee County Museum is host to the 33rd annual Rhubarb Festival. The event promises plenty of good food, entertainment, and a pie-eating contest. 

13. Mole de Mayo

Friday, May 26 through Sunday, May 28 | 18th Street and Ashland Avenue
The 14th Annual Mole de Mayo festival brings together local chefs and restaurants in competition for who has the greatest mole—a Mexican staple. There will also be an outdoor market featuring other businesses and crafts at this Pilsen event.

14. Mayfestiversary

Saturday, May 27 and Sunday, May 28 | Ravenswood and Belle Plaine Avenues 
Begyle Brewing and Dovetail Brewery are back to host their annual spring party in Ravenswood. There will be music and food trucks, and the $5 suggested donation goes towards local pantry The Friendship Center.

15. Maxwell Street Market

Beginning Sunday, May 28, 2023 | 800 S. Desplaines St.
Another city market returns to Maxwell Street on Memorial Day weekend. Visit this farmers market from 9:00 am to 3:00 pm every Sunday until the end of October.