Lollapalooza is taking over more of Chicago than just Grant Park this week.
Ahead of his July 31 Lollapalooza performance, Grammy-winning British rocker Yungblud has teamed up with Tall Ship Windy to transform Chicago’s official tall ship into a black-sailed pirate ship, marking the first artist collaboration in the attraction’s 30-year history.
For one week only during Lollapalooza, the traditional four-masted schooner is sailing beneath custom black sails bearing Yungblud’s name, giving the lakefront Chicago sight a rock-and-roll makeover.
Photo by Barry Butler.
Celebrating its 30th anniversary in 2026, Tall Ship Windy has long been a Navy Pier favorite, offering daily sailing excursions with panoramic views of the city skyline.
During the limited-time Yungblud x Tall Ship Windy sailings this week, the ship’s bar will offer special Yungblud-inspired cocktails — Lowlife Lemonade, Mars Margarita, and Cotton Candy Sky Cocktail. Every sailing this week also includes a chance to win YUNGBLUD merchandise, and guests who photograph the ship and tag @tallshipwindychicago on social media will be entered to win complimentary Tall Ship Windy tickets.
Yungblud performs Friday on Lollapalooza’s Bud Light Stage ahead of headliners and Chicago natives, The Smashing Pumpkins, with whom he released a reimagined version of “Zombie” earlier this year. Both artists also built anticipation for their main stage sets with Lollapalooza aftershows at the Riviera Theatre on Wednesday and Thursday nights, with Pumpkins frontman Corgan joining Yungblud onstage Thursday night for “Zombie.”
Born Dominic Harrison, Yungblud is known for blending alternative rock, punk, and pop with an outspoken message of individuality and self-expression. Earlier this year, he won the Grammy Award for Best Rock Performance for “Changes (Live From Villa Park),” recorded during the Back to the Beginning concert celebrating Black Sabbath.
Can’t make Lollapalooza in person? Livestream the festival at home on Disney+ and Hulu starting at 4 p.m. ET / 3 p.m. CT every day from July 30 through August 2. Get the full Lollapalooza livestream schedule here.
If you enjoy experiences like Tall Ship Windy, consider supporting Navy Pier, the nonprofit organization that operates the iconic lakefront destination. Donations help fund free public programming, community events, arts and cultural initiatives, and improvements that keep the Pier welcoming for millions of visitors each year.
Beyond the music, Lollapalooza supports a variety of community initiatives, including Ingenuity’s work to expand arts education in Chicago Public Schools. Born from a citywide effort to address inequities in arts education, Ingenuity works to ensure every CPS student has access to the arts. Learn more about the organization’s work and make a donation in honor of Ingenuity’s 15th anniversary.
Brooke McDonald is the editor in chief of Better Magazine. She regularly reports on entertainment, theme parks, and travel and her work has appeared in Insider, The Points Guy, Parents, TravelPulse, Scripps News, and more. Her favorite nonprofits to support include World Central Kitchen, the ACLU, and the Vitalogy Foundation. Find her on Instagram @brookegmcdonald, Threads @brookegmcdonald, Bluesky, and X @BrookeGMcDonald.
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