Penthouse Pair

Consisting of two penthouses high above Chicago, this home is made for groups who want breathing room and serious city views. The living and dining spaces are light-filled and expansive, with the skyline as a constant backdrop – and each bedroom has its own bathroom, so logistics stay simple even for larger gatherings. A shared terrace with a barbecue area sits above the rooftops, and an indoor pool means there's no reason to leave when the weather turns. It's steps from Millennium Park too, so you're right in the heart of things.

Home truths:
* Your host operates several homes here, so the exact view, layout and furnishings might differ slightly from the photos. However, the overall quality should remain the same.
* This home is made up of two separate penthouse apartments that are paired together for group bookings. If your group values some private space within the larger stay, that layout works well.
* 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.
* You'll have access to the on-site swimming pools, rooftop lounges and terraces, fitness centre, social and game lounges, workspaces, and dining terraces here. They're shared with the building's other residents.