Walk ten minutes from the Museum of Contemporary Art to your room at the year-old dana Hotel and Spa (from $159). The floor-to-ceiling windows offer grand city views even on the lower floors, and an indoor-outdoor sky lounge just opened on the 26th floor.
Get a wake-up call from President Obama (or a good mimic) at the Wit (from $199), located on historic State Street just 200 feet from the river. The double-paned windows block out the noise from the adjacent El train.
Share sidewalks with working artists from the cooperative Flat Iron Arts Building when you stay at the nearby Wicker Park Inn (from $139), a family-friendly B&B with six rooms on-site and two sizable apartments across the street.