Southwest® flights from Seattle/Tacoma to Chicago-Midway from $147

Fans of the Seattle Center Monorail will feel right at home when they deplane at Chicago Midway International Airport if they’re interested in taking public transit during their visit—the Orange Line of the ‘L’ is right there to whisk you directly to downtown Chicago. Rideshares and rental cars are also an option, of course. Whichever you choose, your Chicago adventure awaits—get going!

Mentioning the Windy City outside of the Chicagoland area often evokes gangster and mobster imagery. If that’s of interest, gangster and crime tours abound. Visit old hot spots and watering holes and homes, renown landmarks, and take a peek at the changing neighborhoods surrounding these relics. When it’s time to stop off for a bite to eat, you’ll find some of the tastiest Chicago classics in and around the neighborhoods beyond downtown and the Loop. A Chicago-style hot dog is a dragged-through-the-garden treat not to be missed, and who can visit without having a slice (or two, or five) of pizza?