Southwest® flights from Baltimore/Washington to Chicago (Midway) from $89

Baltimore may be Charm City, but you'll see that Chicago is just as charming. When you fly in from the D.C./Baltimore Area, you'll deplane at Chicago Midway International Airport on the Southwest side of Chicago. Unlike the East Coast, where everything's exceptionally close together, the Midwest has a little more room to stretch. Thankfully, Midway is only a half-hour Orange Line ride on Chicago's venerable CTA public transit system away from downtown—or the Loop, as the locals call it, named for the elevated train ring around the area. Once there, the city stretches before you, easily accessible by bus, train, automobile, or even rental bike!

Hungry for a taste of local cuisine? Sample some of the best plates in the culinary world on a trip to Restaurant Row in the West Loop (just west of the Magnificent Mile—consider a reservation after a day of shopping). It's rumored that chicken vesuvio originates from here, but who's to say, really? Looking for a meal with fewer frills? Try a slice of Chicago-style pizza (deep dish, stuffed, or thin) or have a dragged-through-the-garden, Chicago-style hot dog—just don't ask for ketchup!