There’s a Chicagoan in the White House and an ex–White House shot-caller running City Hall, so it’s not a complete stretch to call Chicago America’s true political capital. (And that’s before you recall that the former mayor’s brother, a Chi-town political machinist to the core, is now Obama’s chief of staff.) Mayor-for-two-weeks Rahm Emanuel may be the only man not named Richard Daley with enough juice to face off against the bumptious City Council, but he has his work cut out for him. Even with start-ups like Groupon and Threadless galvanizing the city’s entrepreneurial ranks, Chicago has big problems: Daley left behind a gaping budget deficit, a dire pension crisis, and a parking-meter-privatization deal that rankles everyone but the Morgan Stanley bankers who arranged it. Yet Chicagoans are a resilient lot, and no fiscal debacle can obscure what they really love about their town: enthralling architecture, a restaurant scene awash in Michelin stars (not to mention ridiculously good Italian beef sandwiches), a crackling baseball rivalry, and a majestic-blue backyard that magically transforms into a beachfront paradise at the break of every summer.
Edited by Kera Bolonik. Additional reporting by Michael Alan Connelly, Ted Cox, and Lauren Murrow.