Before Farewell Speech, Chicagoans Reflect On President Obama's Legacy Kim Chisholm stood with thousands of others in the bitter cold this weekend to get a ticket to Obama's speech. "I'm so excited," she says. "History in the making. I never made it to the White House, but I will see him here in Chicago." Chicago officials say there are pluses and minuses to having such close ties to the Obama administration. On Monday, the city won a federal grant for nearly a billion dollars to upgrade a major portion of the city's elevated commuter rail line. Mayor Rahm Emanuel, Obama's first White House chief of staff, worked to make sure the funding came through before the administration changed hands. "This will over the next four years create 6,000 jobs in the city of Chicago," he says. Illinois' senior U.S. Sen. Dick Durbin says the city's been able to make significant infrastructure improvements with the help of federal funds, including high speed rail and upgrades to O'Hare International Airport. "Time and again, the Obama administration has not forgotten where he came from," Durbin says. "Has not forgotten the city of Chicago." POLITICS Obama's Farewell Address: How Presidents Use This Moment Of Reflection That's in part because the administration included a bevy of Chicagoans as cabinet members and advisers, such as former Education Secretary Arne Duncan, advisers Valerie Jarrett and David Axelrod, and Commerce Secretary Penny Pritzker. Tuesday night's speech and talk about an Obama legacy in Chicago is much more personal for some. Jacky Grimshaw worked in Chicago government under Harold Washington, the city's first black mayor, and was Obama's next-door neighbor for years. She says the country's first black president faced the same sort of opposition that Washington did and both men prevailed. "And he put through the stimulus package that allowed communities across the country to deal with infrastructure projects that needed to get done," Grimshaw says of Obama. Some community organizers take a more nuanced stance. Jitu Brown of the Institute for Educational Leadership says while the president conducts himself with grace, he disagrees with many of his administration's education policies. "And I think the disappointment is in a president who started as a community organizer, I would have really hoped there would have been space to really listen to the voices of the people directly impacted," Brown says.