Cyclists take over a 15-mile stretch of Lake Shore Drive this weekend for the annual Bike the Drive. Bike the entire 30-mile loop or opt for a shorter route with five separate entry points. Rest stops offer water and snacks; a post-ride festival includes giveaways, music and an optional pancake breakfast ($13). Helmets are required, and organizers recommend starting no later than 7:30 a.m. to get the most out of your ride.
Details: 6:30-10:30 a.m. Sunday along DuSable Lake Shore Drive from Bryn Mawr Avenue to 57th Street. (Accompanying festival runs 8 a.m.-12:30 p.m. Sunday at Butler Field, 235 S. Columbus Drive.) $64-84; $18 for ages 17 and under / MAP
Looking for more events? Taste of Polonia, West Loop Art Fest and North Coast Music Festival all return this weekend. Check out those and more of the season’s upcoming festivals in our 2023 Chicago Summer Festival Guide.
For the first time, the Chicago Labor Day Parade will take place in Pullman. Presented by the Chicago Federation of Labor, the parade will showcase the neighborhood’s ties to Chicago’s labor movement. Eddie Fest follows with a live band, beer garden, bounce houses, kids’ activities and hands-on train exhibits.
Details for the Chicago Labor Day Parade: Parade steps off at noon Saturday at Cottage Grove Avenue and 108th Street, moving south along Cottage Grove to 113th Street. Free / MAP
Details for Eddie Fest: 1-6 p.m. Saturday at Arcade Park, 11132 S. St. Lawrence Ave., and Pullman (George) Park, 11101 S. Cottage Grove Ave. Free / MAP
Celebrate St. Patrick’s Day in September with Long Grove’s Irish Days. The three-day festival showcases all things Irish with bagpipers, folk bands, dancers, food and beer. Bring your pooch for the Irish Dog Competition, where all dogs in costume are paraded before a panel of kid judges. Men are welcome to strut their stuff at the Best-Looking Men’s Legs in a Kilt Contest. (Don’t own a kilt? Borrow one for free.)
Details: 10:30 a.m.-8 p.m. Saturday, 10 a.m.-7:30 p.m. Sunday, 11 a.m.-4:30 p.m. Monday at Long Grove Fountain Square, 228 Robert Parker Coffin Road in Long Grove. Free / MAP
The 34th annual African Festival of the Arts delivers cultural programming for the whole family. You’ll find an African market, children’s pavilion, drum village, food court and more. Live music spans several genres, including Afro-Brazilian, reggae, hip-hop and house.
Details: noon-10 p.m. Friday, 10 a.m.-10 p.m. Saturday to Monday at Washington Park, 5100 S. Cottage Grove Ave. $10-$375 (Free on Friday) / MAP
The Chicago Jazz Festival returns with live performances from local, national and international artists at Millennium Park and the Chicago Cultural Center. Learn more on “Chicago Tonight: Black Voices.”
Details: Times and locations vary Thursday to Sunday. Free
Events listed are subject to change. We recommend double-checking times and locations before you head out the door. Want to share your upcoming events with us for consideration in a future roundup? Send us an email.