Pilsen Cabinet of Curiosities

The basics:Sleeps six; from $162
The low-down:A sculpture with a giraffe’s head on an octopus’s body? Why not. It’s just one of the oddball details in this artist-designed space.

Kenwood Mansion

The basics:Sleeps four; from $150
The low-down:The Obamas may have forsaken their nearby manor—but this graystone’s penthouse still has plenty of glamour.

Burnham Harbor Boat

The basics:Sleeps six; $249
The low-down:Live out your childhood pirate fantasies aboard this 33-foot Sea Ray Sundancer. (A captain will cruise you around the lake for an extra $349 an hour.)

Wicker Park Views

The basics:Sleeps 12; from $450
The low-down:It’s a penthouse with a wet bar, fire pit, 12-foot ceilings, and two big decks. Say hello to your Labor Day plans. (But get ready to pay up—each additional guest after six costs another $50.)