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Chilly temps and a few snowflakes are no match for determined rooftop lounge lizards. An expert guide to the best chicago hotels with rooftop bars, featuring the top spots for innovative cocktails, live djs, swimming pools and incredible city and river views, near the millennium pier, navy pier, shedd aquarium and art institute of chicago. All 15 rooftops and chicago's first shuffleboard club and bar in bucktown not only houses multiple bars. Frequently asked questions about chicago.