Kennedy Rooftop

The Kennedy is on top of the Hyatt in Wicker Park, and since you’re not literally in the skyline, you have a sweeping view of the entirety of downtown Chicago. It also has a long menu full of cocktails and bar food, and plenty of tables and couches. It’s a great option for year-round admiration too. In the winter, The Kennedy has heated, private, twinkly domes that you can rent out.