The 606
The Bloomingdale Trail - popularly called "The 606" - is a linear park that connects several neighborhoods on the north side of the city. Though there aren't playgrounds on the elevated trail itself, there are two playgrounds at access points (Walsh Park and De Burgos Park) and a few more playgrounds that are just a few blocks away from the trail. This page highlights some of these playgrounds.
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Walsh Park - Playground
Located at the eastern edge of the 606, Walsh Park is one of the best playgrounds in Chicago. The playground great; the main play structure is massive and is a nice water spray feature and picnic tables. This is a great playground and definitely worth a visit
Churchill Field Park
There isn't a playground in this park, but it is a good spot to fly a kite or have a picnic.
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Dean Park - Playground
Dean Park is several blocks south of the Wood Street access point. But it is a lovely small park on a quiet street great for younger children.
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Wicker Park - Playground
A few blocks south of the Damen access point is Wicker Park. This well-known and popular playground has a very nice playground.
Park 567
No playground here either. But there the serpentine stairs and great views of the Blue Line might interest some kids.
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Erhler Park - Playground
Erhler Park is just a few blocks north of the Milwaukee Avenue access point (that is, leave the trail via Park 567). This playground was redone in 2022 and is a great playground.
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Lucy Flower Park - Playground
This is a nice neighborhood playground just a short walk north of the Rockwell street access point. There is a sandbox, a water spray feature, and a nice set of playground equipment.
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Maplewood Park - Playground
Maplewood Park is a gem of a park. There is a brand-new fieldhouse and a wonderful and accessible playground with new equipment. This park is located two blocks south of the 606 on Maplewood; the nearest access point to the 606 is Rockwell.
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Humboldt Park - North Playground (North and Richmond)
You can exit the 606 at Humboldt and walk south a few blocks to get to Humbolt Park. There are actually five playgrounds in Humboldt Park; there are two on the north side of the park and both are good playgrounds.
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De Burgos Park - Playground
Immediately off the 606, this is a great playground. It is quite small but features a massive spider web net climbing element and a nice mural.
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Palmer Square Park - Playground
If you exit at Albany and head north a few blocks, you can get to Palmer Square Park. This is not a traditional playground but features some interesting play sculptures. This playground is best for little children and this park is a great spot for a picnic.