The Hoxton, Chicago

The pool

• Rooftop pool above Cabra
• City views
• Early May–October
• $20 Sunday day passes

Why it's on the list

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.

The stay

The Hoxton is the restaurant-district one — it opened in 2019 in Fulton Market, the old meatpacking blocks that have become Chicago's most exciting eating neighborhood, and put Stephanie Izard's Peruvian rooftop Cabra upstairs beside the pool. Staying here trades the lake and the Mag Mile for the West Loop's restaurant row, which for a food-first trip is the right trade. At $$$ it's the brand's usual good value for the design — the pick if dinner reservations are the itinerary, and the $20 Sunday day pass is the cheapest way to audition the roof first.