Alliance Bakery & Cafe

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

An all-day brunch restaurant on the ground floor of the Robey hotel in Wicker Park, near the Damen Blue Line and the 606 Trail.

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 West Town park with a large fieldhouse offering an indoor pool, two gyms and a playground -- useful for a rainy day.

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.

Chicago's original kayak and paddleboard outfitter, operating since 1999, renting boats and running guided tours from a dock on the Chicago River.