The 7 Best Labor Day Plans in Chicago

There’s no rest for music lovers, barbecue eaters or circus goers during Labor Day weekend in Chicago. The last major holiday of summer arrives in CHI Town with a host of holiday events, concerts, outdoor food fests, and art fairs. Here are our favorite things to do on Labor Day in Chicago.
Swing at the Chicago Jazz Festival
For over four decades, the Chicago Jazz Fest has been a Labor Day tradition. A few weeks after the passing of jazz great Duke Ellington in 1974, friends and musicians gathered to honor the late icon in an event that would be repeated yearly and eventually transform into one of the nation’s premiere jazz festivals. Now, world-renowned jazz players swing into town for a week of bebop, big band and Latin jazz at a number of stages around Millennium Park. And it’s all free, so you have no excuse not to turn out.
201 E Randolph St, Chicago, IL 60602
Relax with the City’s Best Chefs at a BBQ
At the summer barbecue series at Sportsman’s Club, chefs from some of Chicago’s top restaurants swing by on weekends to man the grill. Show up early (the events are first come, first served), pay $20 at the door, and receive a heaping plate and a drink pairing. You’ll find cool kids from the restaurant industry and other chic barbecue lovers. The summer line-up includes collabs with major venues like Elske and Lula Cafe, but the September 1 meal features rebellious French outfit Cafe Marie-Jeanne.
948 N Western Ave, Chicago, IL 60622
Dance, Dance, Dance at North Coast Music Festival
Lollapalooza may be over, but that doesn’t mean you’re done with great summer music festivals. If jazz isn’t your thing, head to Huntington Bank Pavilion at Northerly Island for the North Coast Music Festival, now in its 10th year. Billed as “Summer’s Last Stand,” the two-day event includes performances by Major Lazer, Bassnectar and Jai Wolf, among a slew of other performers.
Stuff Yourself with Crustaceans
Every year the Great American Lobster Fest takes over Navy Pier for an all-out crustacean binge. The entry-level experience gets you an entry token to be exchanged for a 1.25-pound lobster or a lobster roll, both accompanied by corn on the cob, potatoes, dinner roll, and of course lots of melted butter. A VIP ticket comes with four drink tickets too. The event runs Friday, Saturday and Sunday so you have three days to fill up on all that buttery, lobstery goodness.
600 E. Grand Ave, Chicago, IL 60611
Rekindle Childhood Wonder at the Circus
You may not have visited a circus since, well, ever, but Labor Day weekend provides the perfect excuse to indulge in a little child-like wonder with Midnight Circus. The contemporary circus group performs at Ridge Park on September 28 and 29. Plus you can feel good about attending, since Midnight Circus works to engage every community where they perform with fundraising and local participation.
9625 S Longwood Dr, Chicago, IL 60643
Shop African Goods at an Arts Festival
Step into Washington Park over Labor Day weekend and find yourself in a wonderland of rich textiles, eye-catching jewelry, elegant pottery and historical artifacts. The African Festival of the Arts returns for its 30th year, bringing not only purchasable goods to the festival grounds, but also music, books, family-oriented activities, and food all celebrating the rich heritage of African nations and the Diaspora.
5531 S. Martin Luther King Dr., Chicago, IL 60637
See Fireworks from Navy Pier
No American holiday is complete without colorful explosives in the sky. For your patriotic fireworks fix, head to Navy Pier, where the show kicks off on August 31 at 10:15 p.m.
600 E Grand Ave, Chicago, IL 60611