Southwest® flights from Washington, D.C. (Reagan National) to Chicago (Midway) from $50

Discover what keeps the City of the Big Shoulders standing tall. Take the iconic skyline, for example: The Willis Tower (or the Sears Tower, as Chicagoland lifers still call it) is the tallest building in the Western hemisphere—and you can venture over the edge of it when you visit the Chicago Skydeck Ledge! Fancy peering straight down from 1,353 feet above the streets of downtown Chicago? Maybe you’d prefer to view the iconic architecture of the city from safely at sea level. There are walking tours and boat tours (both boozy and family friendly) from the Chicago River and on Lake Michigan.

There’s much more to see in the Windy City than what the Loop (what Chicagoans call downtown) has to offer. Hop aboard an ‘L’ train (part elevated rail, part subway, all adventure) or bus, and let the CTA take you to the far reaches of the city. Chicago is built of 77 community areas, each of which has something for you to explore. From national institutions to neighborhood haunts, the less commercial areas of the city are just as entertaining as the Mag Mile or Restaurant Row—maybe even more so. Don’t forget to treat yourself to a slice of Chicago-style pizza (locals will tell you it’s actually the thin-crust kind, not the deep dish or stuffed).