September 26th – 29th: 7 Chicago Events to Checkout this Weekend

This weekend, find your next fall fashion item as you shop Randolph Street Market’s Choice of Charity. Taste dishes from some of the best restaurants and chefs in Chicago at Chicago Gourmet. Raise awareness for homeless youth with local music in the South Loop. Hear the sounds of jazz—all on the South Side of Chicago. Checkout seven of the best Chicago events this weekend, plus more things to do in the latest Weekend Seekers Guide.


Randolph Street Market: Choice for Chairty

Saturday and Sunday | September 28th – 29th| 10:00 a.m. – 5:00 p.m.

Plumbers Hall | 1341 W Washington Blvd. | $10 – $200

Image | Randolph Street Market

Randolph Street Market ends its outdoor and indoor experience this weekend in Chicago. But the season closer is far from a sad farewell. Experience 200 vendors with the best of unique vintage, antique, and repurposed, furniture, art, decor, and much more! Enjoy the market bars and live entertainment. For a full vendor list and other details, visit the website here.

Fleurs de Villes Chicago

Friday | September 27th | 5:00 p.m. – 9:00 p.m.

900 North Michigan Shops | 900 N Michigan Ave. | Free

Fleurs de Villes

Fashion. Drinks. Food—what more could you ask for on a Friday night in Chicago? Fashion and flowers are the focus at 900 North Michigan Shops this Friday. Join the team at Fleurs de Villes Jardin pop-up shop for a free floral demo, workshop, trends presentations, cocktail making and more from Chicago’s top lifestyle gurus and florists. For more details on the floral-forward fall event, visit the event page here.

Food + Drink: 

Chicago Gourmet

Saturday – Sunday | September 28th – 29th | Time Varies

Millennium Park | 201 E. Randolph St. | $0 – $2,015

Chicago Gourmet as featured on The Haute Seekers September 2019 Chicago Events Guide
Image | Chicago Gourmet

Chicago Gourmet, one of the biggest food events in the city, takes place this weekend. As shared in the guide of 32 events to check out this fall, the two-day exhibition features some of the best restaurants, and chefs both locally and from around the world. This year’s theme is inspired by movies, television, and theater. The food event honors Chicago’s culinary achievements and the creative vision chefs, Master Sommeliers, and wine and spirit makers who participate. For tickets and more event details, visit Chicago 

Taste of Haiti Chicago 2019

Saturday| September 28th | 11:00 a.m.

Kizin Creole Restaurant | 2311 West Howard St. | 12:00 p.m. – 11:00 p.m.

Image | Kizin Creole Restuarant

Experience a day of Haitian culture and cuisine this weekend in Chicago. Kizin Creole, the only Haitian restaurant in the city of Chicago is located on the North Side of the city. The annual Taste of Haiti event gives guests the ultimate experience of fine Haitian cuisine, music, and arts. Experience off-menu eats, cooking demos, family activities and more. To learn more about this Taste of Haiti, visit the event page here.


3rd Annual Purple Palooza

Saturday | September 28th | 6:30 p.m. – 9:30 p.m.

REFUGE Live! | 416 South Clark St. | $15 – $20

Image | Stand up for Kids Chicago

Join some of Chicago’s most talented musicians for an evening of music and charitable giving. Stand Up for Kids, located in Lakeview neighborhood, works to establish and build nurturing, supportive relationships with Chicago’s homeless youth while encouraging them to become empowered young adults.100% of the profits will go directly to this local organization. For more details and to purchase tickets, visit the event page here.

Arts + Culture:

Hyde Park Jazz Festival

Saturday – Sunday | September 28th – 29th| Time Varies

South Side Location Varies | Free

Image | Hyde Park Jazz Festival

Check out the 13th Annual Hyde Park Jazz Festival this weekend in Chicago. The collaborative platform is dedicated to supporting the presentation and ongoing development of jazz, particularly on the South Side of Chicago. The free two-day festival features the finest in local jazz, national, and international jazz artists. Learn more about the talented acts taking the stage by visiting Hyde Park Jazz

Edgewater Arts Festival

Saturday – Sunday | September 28th – 29th | 11:00 a.m. – 7:00 p.m.

Granville between Broadway and Sheridan | Free

Image | Edgewater Artists in Motion

If you’re an art lover of any kind, you must check out the 7th Annual Edgewater Arts Festival this weekend in Chicago. This art event gets you in front of emerging Chicago artists. On top of that, you will have unlimited access to explore the unique Edgewater neighborhood over the course of two days. For more details on this event, visit the website for more details.

The Weekend Seekers Guide shares some of the best things to do in the city over the weekend, but there are even more events that make some of our other major lists. For more events, be sure to check out the fall guide as well as the best things to do in September.

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