Memorial Day Wreath Laying Ceremony & Parade
The weekend marks the unofficial start of summer, but it’s crucial to remember its true significance: honoring the U.S. military members who died serving the country. The annual wreath-laying ceremony will take place at Daley Plaza. This year, Sergeant Major Janet Sandoval, a Chicago native with more than 20 years of service in the Marine Corps, will be the keynote speaker. The parade follows the ceremony along Dearborn Street. Join in to pay tribute and cheer the parade.
- Location: Daley Plaza, 50 W. Washington St.
- Time: 11 a.m. ceremony, parade at noon on Dearborn Street from Lake Street to Van Buren
- More Info: Get details at chicago.gov
Sueños Music Festival
This weekend marks the start of the festival season in Chicago with the Sueños Music Festival in Grant Park. Headliners include J Balvin, Kali Uchis, and Fuerza Regida, performing across three stages. If you miss the main event, you can still enjoy one of many after parties around the city, including one featuring Fuerza Regida.
- Location: Grant Park, entry off of Michigan Avenue near Ida B. Wells Drive
- Time: Noon to 10 p.m., May 23-24
- Tickets: Starting from $189 for 1-day general admission (ages 18+)
- More Info: Visit suenosmusicfestival.com
Navy Pier Fireworks
Summer fireworks begin at Navy Pier with displays scheduled for Wednesday and Saturday nights, running through September 5. Enjoy the spectacle without any rainfall to dampen the fun.
- Location: Navy Pier, 600 E. Grand Ave.
- Time: 10 p.m. May 23, with future displays at 9 p.m. Wednesdays and 10 p.m. Saturdays
- More Info: More at navypier.org
Warm Love Cool Dreams Music & Arts Festival
Brought together by Empty Bottle, this festival at Salt Shed Fairgrounds features a diverse lineup including Courtney Barnett, Toro Y Moi, The Jesus and Mary Chain, and Tortoise. Don’t miss out on the Oddball Market between performances.
- Location: Salt Shed Fairgrounds, 1357 N. Elston Ave.
- Time: May 23-24
- Tickets: Starting from $75.20
- More Info: Details at warmlovecooldreams.com
Belmont Sheffield Music Fest
This 41st-year festival provides a neighborhood experience with two stages featuring tribute bands and local entertainment. Explore the market showcasing artisans and small businesses while enjoying food and drink options.
- Location: Around 3200 N. Sheffield Ave.
- Time: 5 p.m.-10 p.m. May 22, and 11 a.m.-10 p.m. May 23-24
- More Info: More details at lakevieweast.com
Mayfestiversary
This Ravenswood festival lets you explore local breweries, two stages, food trucks, and pop-ups, alongside activities for kids. Proceeds from the $5 suggested donation benefit The Friendship Center food pantry.
- Location: Around 1800 W. Cuyler Ave.
- Time: 11 a.m.-10 p.m. May 23 and 11 a.m.-9 p.m. May 24
- More Info: Details at mayfestiversary.com
Randolph Street Market Festival
Kick off the Randolph Street Market Festival with its 23rd annual Garden Party. Experience live music and DJs while shopping among treasures offered by 200 vintage vendors. Indoor shopping is available.
- Location: 1341 W. Randolph St.
- Time: 10 a.m.-5 p.m. May 23-24
- Tickets: From $14
- More Info: Visit randolphstreetmarket.com
The Kid LAROI
Australian singer-rapper-songwriter Kid LAROI brings his “Perfect World” global tour to Salt Shed. Known for hits like “Stay,” his latest album “Before I Forget” tackles themes surrounding a breakup.
- Location: Salt Shed, 1357 N. Elston Ave.
- Time: 6:30 p.m. May 22
- Tickets: From $80
- More Info: Information at saltshedchicago.com
Comedy Bang! Bang!
Scott Aukerman along with Paul F. Tompkins and the rest of the “Comedy Bang! Bang!” crew perform live at Chicago Theatre. While the TV show is no longer airing, this “Ground Beefing” tour continues to entertain fans.
- Location: Chicago Theatre, 175 N. State St.
- Time: 8 p.m. May 28
- Tickets: Starting from $46.25
- More Info: Tickets at msg.com
David Koechner
Character actor David Koechner, known for roles in “Anchorman” and “The Office,” started his career in Chicago. Catch his performance at The Den Theatre this weekend.
- Location: The Den Theatre, 1331 N. Milwaukee Ave.
- Time: 7:15 p.m. and 9:30 p.m. May 22-23
- Tickets: From $31
- More Info: More details at thedentheatre.com
Have an event in Chicago? Email details to [email protected].

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