Kennedy Rooftop in Chicago

Kennedy Rooftop: the whole skyline from Wicker Park

A panorama from the west

Wicker Park, a lively neighborhood northwest of downtown, has no skyscrapers, and that's exactly what makes Kennedy Rooftop worth the trip. Set on the roof of the Hyatt Place, at the intersection of North, Milwaukee and Ashland Avenues, it gazes at downtown from a distance: the skyline unfolds in one unbroken sweep, from the Willis Tower to the former John Hancock Center, above the neighborhood's rooftops. More than 7,000 square feet of terrace hold high-top tables, sofas and a large tent, along with a glassed-in indoor bar. In winter, the bar stays open and offers heated igloos you can reserve.

Presidential cocktails and a bar menu

The drinks menu pays tribute to American presidents: the Quincy Peartini with pear vodka and elderflower, the First Lady with hibiscus gin, and an Old Fashioned dubbed the JFK, at around $14 to $18. From the kitchen, there are sliders, chicken wings, shrimp ceviche, burrata or nachos to share, followed by sandwiches, burgers and flatbreads. Happy hour Monday through Friday (4pm to 6pm) features classic cocktails and small plates for $10, and Tuesdays bring tacos and live music.

Practical information

Open Monday through Thursday from 4pm to 10pm, Friday and Saturday until 11pm, and Sunday from 11am to 4pm. Online reservations are recommended; tables are limited to two hours and ten people, and an 18% service charge is added to the bill. Dress code enforced. The Division station (Blue Line on the “L”) is about 750 meters away.