Floor-to-ceiling glass wraps the living area, framing an uninterrupted sweep of the Chicago skyline and Lake Michigan that shifts from blue to gold depending on the hour. The three bedrooms carry those views too, so you wake up with the city laid out before you rather than catching it only in passing. A rooftop pool terrace and hot tub sit above it all – useful on a warm afternoon, and pretty hard to leave when the sun drops behind the skyline. When you do head out, you'll find Grant Park and the Museum Campus within easy reach, along with an unrivalled dining scene.

• There's no free parking at this home, but your host can arrange paid parking, subject to availability – this must be reserved in advance.$100 / night