Southwest® flights from Baltimore/Washington to Chicago (O'Hare)

When you leave behind the Capitol Region for a visit to Chicago, you’ll find you’ve landed somewhere with plenty of political heft of its own. The Windy City didn’t get its nickname from the blustery lake-effect weather alone; local braggarts and boastful politicians have also been credited with being the origin of the moniker. Whether it’s wind or a lot of hot air, Chicago has plenty worth boasting about.

Another nickname, the Second City, has stuck around long after the population size of Los Angeles outpaced the Chicagoland area, but that hasn’t left a chip on the City of the Big Shoulders. Chicago is home to world-class restaurants, vibrant and eclectic neighborhoods, beloved cultural institutions, and a crosstown baseball rivalry that’s been known to pit brother against brother. Take a ride on the Red Line of the ‘L’ and explore each ballpark or simply to see large swathes of the North and South Sides.