Southwest® flights from Denver to Chicago-Midway from $100

Whether for business or pleasure, Chicago may be calling you away from Denver. While you won't get the same kind of altitude when you visit, you can 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. It's not quite the Rocky Mountain high you're used to, but it's still a thrill. Looking for something at sea level? Check out the walking or boat tour. Several are based downtown, but many venture into one of the city's 77 designated neighborhood areas.

Maybe you're after a slice of famous Chicago-style pizza. Contrary to popular belief, 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. Less crunchy than St. Louis crust, more crispy than a New York City-style slice, the choice of real Chicagoans is sure to please. If your stomach can manage it, sample a slice of each after you land at Midway—or have a pie shipped home to Denver.