The Gilt Sample Sale: Chicago

Planning your weekend in Chicago? Shop ’til you drop at the Gilt Sample Sale, try a variety of wines while exploring businesses in Andersonville, or get active with your family at UNICEF’s Kid Power Month celebration. Or, head to the suburbs for an anniversary dinner and Chocolate Fest.

Disotto Anniversary Wine Dinner


Photo courtesy of Disotto.

May 19

The team at Disotto is celebrating their first anniversary with a five-course chef’s tasting menu and Italian wines. Reservations can be made by phone (224-765-9490) or in person.

The Gilt Sample Sale: Chicago


Photo courtesy of Gilt.

May 19-20

This sale (with designer pieces up to 80 percent off) returns to Chicago with a whole new look and offerings like complimentary monogramming, on-site styling, makeup application, mini massages, pop-ups, light bites, drinks and more. Buy your tickets now and don’t miss out on this luxury shopping event.

Chocolate Fest

Long Grove Chocolate Fest

Photo courtesy of Chocolate Fest.

May 19-21
Long Grove

Visit Long Grove for the annual Chocolate Fest, which will feature not only chocolatey treats, but also live music, a Chocolate Scavenger Hunt, a chocolate pie eating contest and more.

Kid Power Month Celebration

UNICEF Kid Power Band

Photo courtesy of UNICEF USA.

May 20

UNICEF USA is celebrating its Kid Power Band and Kid Power Month this weekend at Chicago Children’s Museum at Navy Pier. Kids will love “Star Wars” activities, a Target crazy maze and more. “Empire” actress Ta’Rhonda Jones will also be in attendance, among other special guests. Learn more about the Kid Power Band and how it gets kids moving while giving lifesaving nutrition here.

Andersonville Wine Walk

Andersonville Wine Walk

Photo courtesy of the Andersonville Chamber of Commerce.

May 21

Explore Andersonville at this annual wine walk featuring 26 local businesses. Participants include Candyality, Milk Handmade, Pastoral, Sparkles Fine Jewelry and The Wooden Spoon.


  • Student Alliance for Homeless Youth invites high school students to attend its 7th annual Paddle Party on May 21 from 4-6 p.m. at the Winnetka Park District Paddle Courts. Students will enjoy paddle and pizza and will be able to learn more about SAHY, which hosts student-led service projects.

Looking Ahead

  • Wilmette’s Full Bloomed Lotus Center for Self Awareness will host “Engage: Transforming Communities” on May 22 from 7-8:30 p.m. at the Community Recreation Center in Wilmette. Guests will hear from Sol Flores, founding executive director of La Casa Norte, an organization that serves homeless youth and families, about their work and how the local community can help.