May Neighborhood Festivals

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(festivals are subject to change)


Lincoln Park Wine FestLincoln Park Wine Fest

May 18-20, 2018

Jonquil Park, 1001 W. Wrightwood

Chicago, IL 60614

Friday: 6-10pm, Saturday: 12-9pm, Sunday: 12-4pm

Admission: $48-50 per person for daily wine tasting pass

Fourth annual tasting event in Lincoln Park/DePaul celebrates fermented grapes with more than 80 varietals at ticketed tastings, food, artists, a deejay and food/wine pairings.



May 18-20, 2018

Roscoe Village, 3100 N. Ashland Ave.

Chicago, IL 60657

Friday: 5-10pm, Saturday & Sunday: 12-10pm

Admission: $10 at gate

Chicago’s Mayfest is the annual kick-off event for our summer festival season. Join us this year as we celebrate our 23rd year and we’ll promise to give you a weekend of endless fun.


Bark in the ParkBark in the Park

May 19, 2018

The Stadium Green next to Soldier Field, 1410 Museum Campus Drive

Chicago, IL 60605


Admission: $40 Adults, $10 Children (3-12), Dogs Free

“Bark in the Park” is the largest dog-friendly party in Chicago. Held by The Anti-Cruelty Society on the Stadium Green adjacent to Soldier Field on Saturday May 19, all proceeds from the event help rescue and care for abandoned and abused animals throughout the region.


Mole de MayoMole de Mayo

May 25-27, 2018

Pilsen, 18th St. at Ashland Ave.

Chicago, IL 60608

Friday: 5-10pm, Saturday & Sunday: 12-10pm

Free Admission; $5 suggested donation

Being held at Ashland and 18th Street in Chicago’s historic Pilsen neighborhood, the 9th annual Mole de Mayo festival will feature mole, pitting local chefs and restaurants against one another to find out whose version of the Mexican staple is best.


Belmont-Sheffield Music FestBelmont-Sheffield Music Fest

May 26-27, 2018

Lakeview, Belmont & Sheffield Aves.

Chicago, IL 60657


Free Admission; $5 suggested donation benefits the Lakeview East Chamber of Commerce

This popular warm weather festival in the heart of the Lakeview neighborhood unofficially kicks off Chicago's summer outdoor street fest season.


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