what to do in Chicago this weekend

Lenny Kravits and Andra Day

When: Thursday, September 3rd; Gates open at 5 p.m. Concert starts at 7:30

Where: Ravinia Festival, 418 Sheridan Road, Highland Park, IL 60035

Why you may want to attend: Lenny needs no introduction but regarding newcomer Andra Day, the Boston Herald says, “… My word, what a voice she has, a powerful, soulful expressive voice that commands attention. She has Amy Winehouse’s jazz chops, Dionne Warwick’s pop savvy and Tina Turner’s playfulness… one of best sets I’ve seen this year.” Check her out yourself before mainstream radio catches on.

More info: Ravinia

what to do in Chicago this weekend
Image: Chicago Jazz Festival

Chicago Jazz Festival

When: Thursday, September 3rd – Sunday, September 6th

Where: September 3rd: Chicago Cultural Center (78 E. Washington St) from Noon – 4:30 p.m. and Millennium Park (201 E Randolph) from 6:30 p.m. – 9 p.m.; September 4th – 6th: Millennium Park only Noon – 9:30 p.m.

Why you may want to attend: “Known for its artistic creativity, the Chicago Jazz Festival is a favorite Labor Day Weekend tradition. It promotes awareness and appreciation for all forms of jazz through free, quality live musical performance. Since 1979, the festival’s mission is to showcase Chicago’s vast jazz talent alongside national and international artists to encourage and educate a jazz audience of all ages.”

More info: Chicago Jazz Festival

what to do in Chicago this weekend
Image: Chad Smith Photography

North Coast Music Festival

When: Friday, September 4th – Sunday, September 6th

Where: Union Park, 1501 W. Randolph, 60607

Why you may want to attend: D’Angelo and The Vanguards, The Roots, The Chemical Brothers…and the list goes on.

More info: North Coast Music Festival

Chicago African Festival of the Arts
Image: Time Out Chicago

African Festival of the Arts

When: Friday, September 4th – Monday, September 7th; 10 a.m. – 10 p.m. daily

Where: Washington Park, 5100 S. Cottage Grove Ave

Why you may want to attend: “Annually during Labor Day Weekend, the Festival grounds in Chicago’s Washington Park come alive in a simulated African village. Attendees are transported across the Diaspora with interactive engagements, vibrant drumming, museum quality and collectible artifacts, colorful and rich handwoven fabric and textile, and [more!]”

More info: African Festival of the Arts

Summer WingFest

When: Saturday, September 5th; 1 p.m. – 7 p.m.

Where:  Bailey Auditorium, 1340 W. Washington Blvd

Why you may want to attend: “For the past 16 years, Chicago’s Best (and original) WingFest, has been held annually indoors every February, and it has grown to the point of peak capacity where tickets sell out in mere seconds. The demand for more wings has beckoned Chicago’s Best SUMMER WingFest, a bigger and better version to be held outdoors as well as indoors… [The event] will feature double the wing-slinging restaurants, live music, games, a street market, craft beer and a full bar. A general admission ticket will be only $40 per person and will include all-you-can-eat wings from up to 12 of the finest chicken wing establishments in all of Chicagoland. One restaurant will be deemed Chicago’s Best Summer WingFest winner…”

More info: WingFest

Pig Roast at Porkchop

When: Saturday, September 5th; starting at 11 a.m.

Where: Porkchop, 941 W. Randolph

Why you may want to attend: “Say goodbye to summer with an amazing BBQ and specialty Sailor Jerry drinks. Norman “Sailor Jerry” Collins became famous for his traditional tattooing in Honolulu. So, in true Hawaii spirit, PorkChop will be roasting a pig on their patio.” Themed drinks will also be available.

More info: Porkchop’s Facebook


9/4/15 – This article has been updated to include WingFest.

9/4/15 – This article has been updated to include the pig roast at Porkchop.