Oakland and Kenwood Tour
There is a cluster of great playgrounds on the southside in the neighborhoods of Oakland and Kenwood. This 'tour' is arranged as a circle; some form of wheels (stroller, bicycle, or scooter) might be helpful to complete the entire tour but a string of two or three playgrounds would also make a fine morning outing.
Holly Park - Playground Park
A small pocket park with some funky equipment, a water spray feature, and a shade pavilion make this an interesting site.
Williams- Davis Park - Playground
A short walk away, this newly renovated playground sits at the base of the 41st Street pedestrian bridge.
Burnham Park - 43rd Street Playground
This playground - renovated in 2023! - is a wonderful playground with modern equipment.
[This tour requires the 43rd Street pedestrian bridge to be open. It is currently still under construction but was slated to be done in 2022...]
Harsh Park - Playground Park
A nice playground on one of my favorite streets in Chicago.
Kennicott Park - Playground
A somewhat standard playground that somehow charms me. Nice rowhouses nearby and a fieldhouse.
Brooks (Gwendolyn) Park - Playground
A wonderful little park with two play structures. If making the full loop, I would recommend returning to Holly Park by way of South Drexel Boulevard.