As Memorial Day weekend approaches, Chicago offers a variety of events and activities to honor the holiday and enjoy the city’s vibrant culture. Here’s a guide to some of the key happenings:
Memorial Day Parade
Chicago’s annual Memorial Day Parade, a tradition since 1870, takes place on Saturday, May 23. The event begins with a wreath-laying ceremony at the eternal flame in Daley Plaza at 11:00 AM, followed by the parade marching down State Street from Lake to Van Buren streets starting at noon. It’s a time for the community to come together and honor those who have served.
Chicago Symphony Orchestra: Pekka Kuusisto
On Saturday evening, the renowned violinist Pekka Kuusisto performs with the Chicago Symphony Orchestra at the Symphony Center. The concert starts at 7:30 PM, offering an evening of exceptional classical music. Tickets are available for purchase.
Candlelight Concerts
For a unique musical experience, consider attending a Candlelight concert at the Wicker Park Lutheran Church. On Saturday, May 23, there are two performances:
- Neo-Soul Favorites: Featuring songs by Prince, Childish Gambino, and more, this concert begins at 6:30 PM.
- 90s Unplugged: A tribute to 90s hits, starting at 9:00 PM.
Both events offer a multi-sensory experience under the gentle glow of candlelight.
Warm Love Cool Dreams Festival
The Warm Love Cool Dreams Music and Arts Festival returns to Chicago’s Salt Shed on May 23-24. Headliners include Courtney Barnett, The Jesus and Mary Chain, and local favorites Tortoise and Whitney. Alongside live music, the festival features the Oddball Market, offering vintage clothing, records, and handcrafted jewelry by local artists. Tickets are on sale for $59.
Chicago Sky vs. Minnesota Lynx
Sports enthusiasts can catch the Chicago Sky as they face off against the Minnesota Lynx at Wintrust Arena on Saturday, May 23. It’s an opportunity to support the local WNBA team and enjoy an exciting game.
Route 66 Centennial Tour
Celebrate the centennial of the iconic Route 66 with the “Get Your Kicks on Route 66” trolley tour. This 2.5-hour experience explores the historic origins of the route, starting at the Art Institute of Chicago and following Adams Street, Ogden Avenue, and Jackson Boulevard. The first tour is scheduled for May 22, with tickets now available.
With a range of events spanning music, sports, history, and community gatherings, Chicago’s Memorial Day weekend offers something for everyone. Whether you’re honoring the holiday or simply enjoying the city’s offerings, there’s no shortage of activities to make the weekend memorable.

