The Clare in Chicago is the perfect place for city-loving retirees to settle. It's not suitable for everyone, but for those who love the cosmopolitan life, it's a great location to make the most of the windy city's cultural, culinary and retail hot spots. Residences are rented on a monthly basis ranging from $2,440 (£1.9k) for a small one-bed, to $5,615 (£4.4k) for a large two-bed, with various options in between.