![Viceroy Chicago](https://www.thehotelguru.com/_images/2e/d4/2ed4d845fce9a95163bb7c8c9ffc8551/600x422.jpg)
Chicago is best enjoyed from a height; its soaring skyscrapers make a striking city skyline! With a nonchalant trendy vibe, you will find many of the city's converted factories and newer glass constructions boast buzzy rooftop bars and, if you are really lucky, a rooftop pool too. The best hotels with rooftop pools in Chicago also happen to be just some of the best hotels in the city. From suave sophistication at a five-star luxury stay to chic boutiques offering that independent flare that our Hotel Gurus are so fond of. So for a spoiling city break, why not browse through our hotel experts' selection of their favourite hotels with rooftop pools?
For a boutique
![The Robey](https://www.thehotelguru.com/_images/2f/4a/2f4aca163ebd4857a82dff153cba4f51/600x422.jpg)
- The Robey is a smart modern boutique hotel set in a striking art-deco building in Wicker Park. Pick this property for the chic whitewashed rooms (many of which have epic city views) and the French-American restaurant. However, the real pull is obviously the rooftop pool and bar.
For luxury
![The Hoxton Chicago](https://www.thehotelguru.com/_images/1f/a9/1fa9e6284a932004e600db7359784e11/600x422.jpg)
- The Hoxton Chicago is a hip luxury choice perfectly blending industrial and retro design. Expect vast rooms, high ceilings, polished concrete, and velvet upholstery. The range of restaurants and rooftop pool with epic views of the city skyline ensure this property won't fail to impress.
- Viceroy Chicago is a magnificent hybrid of old and new; a perfectly preserved 1920's facade attached to a glistening glass tower. Inside you will find the same paradoxes, the rooms are spectacular and so are the views from their floor to ceiling windows. The rooftop bar draws a crowd, as does The Somerset downstairs. Luxury defined.
Still not sure where to book?