Oak Street Beach is a bustling gathering place right on Lakeshore Drive and Lake Michigan. One of my all-time favorite beaches, where you may actually catch a pro-volleyball tournament in the summer. The sand is white and the water is cool, and this stretch of Lakeshore Drive is where it's at in Chicago. You can walk down to Shedd's Aquarium, rollerblade along the sidewalk, or catch some sun on the beach.