3. Promontory Point
Location: 5491 South Shore Dr.
The best view of Chicago won't come from the downtown heights of the Sears (now “Willis”) Tower, but rather from a half-circle of land jutting out into Lake Michigan, eight miles south. On warm spring and summer afternoons, you'll find it teeming with picnics, grills, and the leisurely arc of Frisbees against a stunning backdrop of the Chicago skyline. This open, grassy gem of the Hyde Park neighborhood is a true find—for those willing to avoid the touristy throngs at Millennium Park and Navy Pier, that is.