Southwest® flights from Los Angeles to Chicago-Midway from $99

While Los Angeles may have unseated Chicago as the Second City by population size, there's still plenty that keeps the City of the Big Shoulders standing tall. Take the skyline, for example: This iconic collection of skyscrapers and high rises is famous for a reason. Visit the Willis Tower (or the Sears Tower, as many locals still call it)—the tallest building in the Western hemisphere—and step out onto the famous, four-foot-long Chicago Skydeck Ledge that lets you gaze straight down onto the city streets from 1,353 feet up in the air. Prefer to stay planted on terra firma? There are walking tours in nearly every corner of the City of Neighborhoods, from gangster-era crime tours about Al Capone to architectural tours for lovers of Frank Lloyd Wright. If you'd dig a river-roaming adventure rather than air or land, check out the boat tours on the Chicago River.

Hungry for more of Chicago? When you disembark from Midway, a quick ride on the Orange Line of the CTA will bring you right into the Loop—Chicago's downtown. From there, you can make it to nearly every portion of the city by hopping on the train line of your choosing (or transferring to the vast network of buses). Cabs, rideshares, and rental cars are options too, of course, but the public transit of the Windy City can be an adventure all its own. Connect to sleepy neighborhoods with hidden gems, venture to the Magnificent Mile for world-class shopping, or explore Restaurant Row for Michelin-starred cuisine. Neighborhood bars and hole-in-the-wall hotdog joints, though, are worth the trek into the Bungalow belts (either north or south, your pick) to explore.