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
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. The deck opens in early May and closes in October. Guests and Working From_ members have it Monday to Saturday — but Sunday brings 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.