Chicago's Grant park district skatepark was made to be a world-class skatepark. The skatepark sits surrounded by skyscrapers, multilane roads, train tracks, and minutes away from Michigan lake. On top of that, it is also walking distance from Chicago's main downtown attractions such as museums, parks, exercising courts, and yearly weekend events.
The skatepark itself is very nice and properly kept up routinely as it was built to be a great attraction to city dwellers and visitors alike. it includes lots of ledges, rails, gaps, light posts for evening sessions, and several ramps. One noticeable thing missing is bowls or other transition obstacles.
Overall the skatepark is a great place to skate at and definitely one to keep in anyone's skatepark bucket list.