Steel & Sky

At these two apartments, floor-to-ceiling windows frame the Chicago skyline in double-height living rooms that earn the view, while the terraces outside are framed by the city's ornate architecture – ideal for a slow evening drink. When the pool calls, you're swimming with the whole of Chicago rising around you. Millennium Park and Cloud Gate are a twelve-minute walk, the Chicago Riverwalk's waterfront cafes are a thirteen-minute stroll, and the Art Institute is eleven minutes on foot – which makes these apartments as well-placed for exploring the city as they are for retreating from it.

Home truths:
* This listing is two separate two-bedroom apartments booked together, not a single connected home. If your group wants to move freely between units, factor in that you'll be stepping out into a shared building corridor each time.
* At full occupancy, you'll need to make use of two rollaway beds here. We think they're best suited to children.
* If you're travelling with little ones, your host can provide a Pack-n-Play travel cot. You'll need to request it in advance.
* Guests staying here have access to a range of communal amenities including a pool, conference room, basketball court, gym, media room and rooftop lounge. Availability may vary seasonally and could incur additional fees.