Cafe Robey

A converted 1929 landmark tower in Wicker Park with loft-style rooms. Its rooftop pool is seasonal (May to September) and does not admit guests under 12.

A recently renovated Chicago Public Library branch with regular unstructured "Play Days" using blocks, puzzles and toys downstairs, and a quiet upper level.

A Bucktown playground on a quiet cul-de-sac with a small water-spray feature, a community garden and an open field.

The eastern trailhead of Chicago's elevated rail-trail through the Northwest Side, with a fenced playground and a ground-jet water spray feature at Walsh Park.

A longtime European bakery in Wicker Park known for elaborate custom cakes and pastries, with an espresso bar.

A century-old Chicago ice cream and candy shop known for oversized sundaes served in old-fashioned booths, with both counter takeout and sit-down table service.