If you haven’t already, check out Swagger’s full Chicago City Guide we put together. But if you’re just looking for some top places to take in the skylines, sunsets and good vibes while enjoying a few drinks, check out our list below:
Devereaux – 18th Floor at the Viceroy (1112 N State Street)
Although you access Devereaux via the alley to the left of the hotel, this rooftop has all the art deco elegance and charm that the Viceroy hotel is known for. Enjoy the view poolside or from through the floor to ceiling windows, while you snack on small plates from the hotel’s award-winning restaurant Somerset.
Cindy’s Rooftop – 13th Floor at the Chicago Athletic Association (12 S Michigan Avenue)
This bustling open-air terrace has panoramic views of Millennium Park and Lake Michigan. Open for brunch, lunch, dinner, or a cocktail and a selfie. The cocktail menu is extensive and includes an ‘apothecary service’ with large format cocktails like old fashioneds, negronis, or the 3 litre Jolie Folle Rose (recommended to serve 10 – 20).
LH Rooftop – 21st and 22nd Floors at the London House (85 E Upper Wacker Drive)
High above the Riverwalk and the Chicago River, the LH Rooftop has sweeping views of the most iconic buildings Chicago has to offer, including the Tribune Tower and (like it or not) The Trump. Fine dine inside on 21 or snack on small bites and cocktails on 22. Be sure to sweet talk your way in to the West-facing seating area and enjoy the sunset.
Raised Rooftop – 3rd Floor at the Renaissance (1 W Wacker Drive)
While it’s not the highest rooftop on the list, it actually has one of the best views. Instead of being above the action, you feel a part of it. Raised has a more industrial aesthetic and raw finishes, contrasting the sparkling view and top-end sharable plates. High points for the delightful, unpretentious staff.
Cabana Club – 6th Floor at the Hotel Robey (1616 N Milwaukee Avenue)
Overlooking the city skyline to the East and the Damen Station below, this is the spot that locals and tourists meet and enjoy a frozen cocktail or infused shot. Hang out poolside and dip your feet or lounge in the super-hip, Instagram-worthy indoors. Light eats from the Dips & Snacks section of the menu will keep you going until you plan the rest of your night.
For a full view of Where to Stay, Eat, See and Shop, check out our Chicago City Guide.