Southwest® flights from Detroit to Chicago-Midway from $101

When you deplane at Chicago Midway International Airport, you’re a short Orange Line ride away from the center of the city and access to 77 neighborhoods worth of fun. Rental cars and rideshares are available too, of course, but when you take the ‘L’, you have a chance to take in the unique views from the elevated train system. If views are what you’re after, summit the highest building in the Western hemisphere—Willis Tower (or Sears Tower, as locals still call it). From the famous Skydeck Chicago Ledge, daredevils can step out onto a glass floor 1,353 ft. above the hustle and bustle of the streets below. The views don’t stop there, though. Chicago has architecture tours (by boat or on foot), food tours, mafia-related tours, haunted building tours, and tours amongst the neighborhoods. See for yourself.

While you’re touring the diverse neighborhoods of the city of the big shoulders, don’t forget to eat! Restaurant Row isn’t the only place to find Michelin-starred meals, but hole-in-the-wall dives and local faves abound and deserve your attention. Maybe you’re after a slice of famous Chicago-style pizza—but don’t let anyone tell you deep dish isn’t the only game in town. In fact, there are two kinds of ooey-gooey, larger-than-life pizza styles: deep dish and stuffed. However, Chicago natives actually call thin-and-crispy “party cut” or “tavern style” pizza true Chicago-style pie.