United crewed the flight with all Black employees and the airline hopes it will inspire others to join the aviation industry.
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"The entire crew from dispatch, mechanics, the crew members, the pilots - everybody is Black. This is just amazing and I'm so thrilled to be a part of this experience," said United Airlines pilot Deon Byrne.
United Airlines Flight 1258 took off from Bush International Airport Saturday morning with a ceremonial sendoff for the all-Black crew in honor of Juneteenth.
"Being able to do a flight like this is a huge deal. It's a big deal for me. Very thankful for it,' said United Airlines flight attendant Nathan Pickney.
The Boeing Dreamliner landed at O'Hare, pulling up on the tarmac under a water salute to mark the historic moment. The members of the all-Black crew greeted with cheers at the gate.
For United Airlines workers, the momentous occasion goes beyond just this flight.
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"To let someone know that when they walk on an aircraft that they can see someone that looks like them, that's exciting," Pickney said. "That's exciting and it's motivating as well."
The airline hoping the Juneteenth celebration will inspire future aviators and airline professionals.
"This holiday is about celebrating our freedom, celebrating our Black heritage," said Jessica Kimbrough, United Airlines chief diversity, equity and inclusion officer, "And today's event is just a wonderful celebration of what's possible."
This Juneteenth flight comes just two months after United Airlines pledged to diversify its pipeline of pilots, with a goal of training thousands of people of color by 2030.