Labor Day may mark the unofficial end of summer, but you’d never know it from the remarkable array of activities in Chicago. Enjoy the days with a slew of amazing summer festivals and events!
A Labor Day tradition returns! Who makes Chicago’s Best Burger? Taste and judge the creations of a dozen Chicago eateries at the Roscoe Village Burger Fest, at Belmont & Damen for a mouth-watering Labor Day weekend Friday, September 3- Sunday, September 5. Far more than a burger fest, the streets of Roscoe Village are alive with two stages of rockin’ music, arts & crafts and the action-packed “Kids Zone” ‘Guests even have the opportunity to vote for Chicago’s Best Burger! A $10 suggested fest donation benefits the programs and services of the Lakeview Roscoe Village Chamber of Commerce.
The City of Chicago presents a special evening of Gospel music on Friday, September 3, as part of the City’s ‘Chicago in Tune’ series at Millennium Park from 5:30–8:30pm. Hosted by Jonathan McReynolds and Inspiration 1390’s Sonya Blakey and DeAndre Patterson — the program includes a special award to producer Sasha Daltonn and feature LaShon Brown; a celebratory music tribute to Rev. Dr. Clay Evans, Pastor Maceo Woods, Bishop Willie James Campbell and ArchBishop Lucius Hall featuring The Carson Sisters, Nicole Harris, and Illiana Torres.
The annual Chicago Jazz Fest is a Chicago institution, but in lieu of the four-day event, Chicago in Tune, along with the Jazz Institute, presents a free night of jazz in Millennium Park on Saturday, September 4, 5:30–8:30 pm, featuring Ari Brown, Marquis Hill and Lizz Wright. Featured performer Ari Brown is a composer, arranger, tenor saxophonist, pianist and educator. He has performed with many music greats including Anthony Braxton, Muhal Richard Abrams, Lou Rawls, B.B. King, Chuck Berry, Elvin Jones, Andrew White, Della Reese and Billy Eckstein.
Travel the 30-mile loop of the newly renamed Jean Baptiste du Sable Lake Shore Drive on Sunday, September 5 at Chicago’s annual Bike the Drive. All ages and skill levels are welcome. You can start the ride anytime between 5:30am and 9:30am, but organizers recommend starting no later than 7:00am to get the most out of your time on the Drive. Regardless of vaccination status, participants must wear a mask in the festival & rest stops and whenever you can’t maintain a distance of 6 feet from others. Admittance to a post–ride festival with food, live music and fun activities for kids is included in the admission price of $18 kids, $60 adults. Meet at Butler Field, 235 S. Columbus Drive, Chicago..
Hey, Pitchfork Music Festival fans! Prepare for the 2021 festival with the Pitchfork Music Film Series, at the Music Box Theatre, 3733 N. Southport Ave, Chicago, from Monday, September 6 (Labor Day) to Wednesday, September 8. Pitchfork and the Music Box showcase some of our most beloved music films, presented with extraordinary guests in conversation with Pitchfork editors. Films include ’20 Feet from Stardom’ with special guest Jamila Woods at 7pm. Ahead of the screening, Jamila will be in conversation with celebrated journalist and Pitchfork contributor Adrienne Samuel Gibbs. All Wilco fans will enjoy ‘I am Trying to Break Your Heart’ with Special Guest Glenn Kotche, Tuesday, September 7th at 7pm. On Wednesday, September 8, the 20th Anniversary of ‘Josie and the Pussycats’ will be celebrated with co-director and writers Deborah Kaplan and Harry Elfont, with Pitchfork Staff Writer Quinn Moreland. Tickets are $15 apiece for each movie.
Alison Moran and Dean’s Team Chicago