Gino's East

An all-suite extended-stay hotel one block off Michigan Avenue, with full kitchens in every suite and free hot breakfast, an easy walk to Millennium Park and Navy Pier.

Park with a playground.

A two-level doll store and cafe inside Water Tower Place where kids can shop, get a doll's hair styled, and eat lunch alongside their doll at a reserved table.

An upscale downtown steakhouse that keeps a kids' menu and high chairs on hand, with staff attentive to family celebrations.

A Streeterville hotel near the Mag Mile with a compact 19th-floor indoor pool called Splash.

The observation deck on the 94th floor of the former John Hancock Center, now branded 360 Chicago, with a fully accessible entrance and family restrooms.