People.com Politics The Obamas' Portraits Are Going on Tour, Starting Where They Had Their First Date: ‘A Homecoming’ "This is the location that has shaped the arc of their professional lives, and it's where they started their family. It's a homecoming," a museum official tells PEOPLE By Virginia Chamlee Virginia Chamlee Politics Writer - PEOPLE People Editorial Guidelines Published on June 1, 2021 01:59 PM Share Tweet Pin Email From left, center: Barack and Michelle Obama in 2018 after an unveiling of their official portraits. Photo: SAUL LOEB/AFP via Getty Barack and Michelle Obama are going back to Chicago — in a way — and to where their love story first began. The official portraits of the former president and first lady will soon go on a nationwide tour, beginning June 18, at The Art Institute in Chicago. It's only fitting that the five-city tour of the portraits — Kehinde Wiley's painting of President Barack Obama and Amy Sherald's of Mrs. Obama — kick off in Chicago, Art Institute Director of Interpretation Emily Fry tells PEOPLE. "It was particularly exciting that Chicago was chosen to be the very first stop and it's something that we really want to honor, because the Obamas and Chicago are inextricably linked," Fry says. "This is the location that has shaped the arc of their professional lives, and it's where they started their family. It's a homecoming." What's more, as Fry notes, the Chicago debut of the traveling exhibit is fitting considering the Art Institute was the site of the Obamas' first date. "The museum is really in the heart of Chicago but it's also the site where they started their relationship," she says. The tour, organized by the National Portrait Gallery, also marks the first time the portraits have traveled outside of Washington, D.C., and will be the first time the two works have been exhibited in the same space together, since they were in different areas of the portrait gallery. Barack Obama Reveals How the White House Strained His Marriage — and How He & Michelle Got Back to 'Deep Love' Michelle LaVaughn Robinson Obama, 2018. Oil on linen. National Portrait Gallery, Smithsonian Institution. Amy Sherald/Courtesy of the Smithsonian’s National Portrait Gallery Barack Obama and Michelle Robinson met while working at the Chicago law firm Sidley Austin (at the time, the future president was working as a summer associate and his future wife was his adviser). Their first date — which took place in 1989 and was the subject of the 2016 film Southside with You — was lengthy, spanning an entire day. The couple visited the Art Institute of Chicago, had lunch in the museum's courtyard, had a drink on the 99th floor of the John Hancock building, saw Spike Lee's Do the Right Thing and took a long walk down Michigan Avenue. "He showed all the sides," Mrs. Obama told CNN in a 2008 interview. "He was hip. Cultural. Sensitive. The fountain, nice touch. The walk, sensitive." "Take tips, gentlemen," Mr. Obama added then. Barack Still Tucks Michelle In at Night and More Sweet Details of the Obama's 27-Year Love Story The museum is also mentioned in both of the couple's memoirs. "Both in Becoming and Promised Land, they recount going to the Art Institute at various points," Fry says. Michelle Obama notes that her father took classes at the school of the Art Insitute, and she recalls climbing into her dad's Buick to visit the museum as a child." The artworks themselves are also significant in that they were created by the first Black artists to paint an official portrait of a president or first lady. "The Obamas have this long history of collecting and presenting — even during Obama-era in the White House — art that really pushed the boundaries of historical cannon," Fry explains. "They often represented Black artists in their collection and when they had this opportunity to select artists to paint their own portraits, I imagine that really shaped their decision." Barack Obama, 2018. Oil on canvas. National Portrait Gallery, Smithsonian Institution. Kehinde Wiley/Courtesy of the Smithsonian’s National Portrait Gallery Wiley's portrait of President Obama is grand in scale — life-sized, but with a sense of approachability, Fry says. "Kehinde Wiley is known for creating these portraits that take figures and place them in a grand scale," she says, "and taking European, traditional approaches and flipping them and challenging ideas of privilege and power." That means that although the portrait of the former president conveys a sense of power, it also depicts Obama leaning forward and with gray hair. Sherald's portrait of Mrs. Obama, meanwhile, is similarly iconic, though "her pose and eye contact is represented as someone who is very open, accessible and inclusive," Fry says. Viewing the portraits side-by-side, as they will be displayed in Chicago, will be impactful, Fry says. "Side-by-side creates a totally different conversation," she says. "In the Chicago installation, they will be together in a room and the room proceeding the portraits will have information about how the portraits were made, along with a very Chicago narrative featuring a map of key moments and locations that had impacts on the Obama's lives." The Famed Barack and Michelle Obama Portraits May Be Coming to a City Near You Following the debut in Chicago, from June 18 to Aug. 15, the portraits will move on to the Brooklyn Museum, the Los Angeles County Museum of Art, Atlanta's High Museum and then Museum of Fine Arts Houston. As National Portrait Gallery Director Kim Sajet said in a January statement, according to The New York Times, "This tour is an opportunity for audiences in different parts of the country to witness how portraiture can engage people in the beauty of dialogue and shared experience." The tour is expected to last until May 2022.