Sky & Swim · IL
Chicago's architecture from pool level is a different argument — you're not looking at a skyline so much as a portfolio. The city was built to be looked at, and the right pool lets you do exactly that.
3 picks · Gold Coast & Fulton Market
Chicago's rooftop pools compete with what may be the finest collection of buildings any American skyline has produced. The three here have the views to justify the comparison.
Eighteen floors up in the Gold Coast, the Viceroy trades the Loop's architecture for Lake Michigan — a guests-only rooftop deck beside Pandan, where on the right afternoon the water and the lake read as one blue plane. Opens May 1, and worth timing a trip around.
The Hoxton stacks a rooftop pool above Cabra's Peruvian rooftop restaurant, with the city filling the frame. Guests and Working From_ members have it Monday to Saturday — but Sunday brings $20 walk-up day passes, which is the cheapest way onto a good Chicago roof.
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.