DoubleTree by Hilton Chicago – Magnificent Mile

The pool

• Rooftop pool
• Downtown views
• Cabanas
• Seasonal
• Day passes from $45

Why it's on the list

High above Streeterville, a seasonal rooftop deck with a panoramic downtown sweep, cabanas for the afternoon, and day passes from $45. Unfussy, well-placed, and a real value for the elevation.

The stay

The DoubleTree is the straightforward sightseeing base — an unfussy big hotel in Streeterville, two blocks off the Magnificent Mile with Navy Pier, the Water Tower, and the lakefront all on foot. Nobody books it for the design; you book it for the address and the rooftop deck, and both deliver. At $$ it's the value way into this part of downtown — the pick for a first-visit or family Chicago trip where the days are for the city and the deck is for the late afternoon, remembering the pool runs roughly Memorial Day to Labor Day.