Recommendations
Brighton Park Community Campus (Park 596) - Playground
Very interesting equipment. A bit of a trek but - again - interesting equipment. Decent water spray feature too.
Bartelme Park - Playground
A really interesting structure. They also do a ton of movies in the park so it could be a double feature!
Edwin C. Berry Playground
Cool structure and climbing wall - the green roof just to the south is an intersting picnic area and place to stroll. 31st street beach is a decent beach too. Don't park in the parking garage - park off LSD just north of the playground.
Elizabeth Benton Playground
Playground is good (not unbelievable) but the park is my favorite downtown park (which I like way more than Maggie Daley).
You can validate parking at the nearby Marianos and get 2 hours free parking.
Walsh Park - Playground
Solid playground. Right at on the eastern edge of the 606 trail. Some picnic tables and a gentle water spray feature.
Senn Park - Playground
Near Andersonville. It has a large-ish structure and I believe they are getting an upgraded spray feature (and nature play area)?
Supera Park - Playground Park
Very strong boat theme - which is neat. A super short walk to Jonquil Park.