Do you want the most amazing hotel experience when visiting Chicago? Then you should keep reading. Even though this is the 3rd largest city in the US, packed with sky-high buildings, finding a rooftop pool here is not an easy task. Which makes the ones available even more exclusive, and this complete guide very handy.
Update: This article was updated on March 31th, 2025, with new information, new hotels, updated photos, booking links and insider tips.
Use the booking links provided in the article to check availability, prices and to book your stay. We dare to promise you an amazing hotel experience at any of these spots!
Our complete and up-to date guide to the 8 Best Hotel Rooftop Pools in Chicago - 2025 feature all info you need about each rooftop, all at the same place, so you don’t have to scroll around on several different sources finding it.
For each rooftop, this guide presents:
We are full-time rooftop reviewers and content creators. Since launching The Rooftop Guide in 2015, we’ve visited over 1 200 rooftop venues worldwide.
Except from our own experiences and insights, we also work closely with thousands of rooftops and local reviewers, so we can secure correct and updated content for all our guides & articles.
With our vast experience and exclusive focus, we can present you with the most complete and up-to date guides about rooftop venues. And with our insider tips and knowledge, we can guide you to the best and most suitable rooftops for your own needs.
Whether you’re looking for an upscale rooftop dinner, a laid-back rooftop brunch, a vibrant rooftop party or a luxurious hotel rooftop pool, we’ve got you covered.
In short: Found just minutes away from the Magnificent Mile shopping district, the suberb hotel Viceroy Chicago offers premium location, along with a top class rooftop experience. Set 18 levels above the busy streets, the terrace holds both a lovely rooftop pool, as well as a stylish rooftop cocktail lounge.
What we say: Among the Chicago hotels with rooftop pools, Viceroy is a real winner if you ask us, The rooftop pool is open seasonally and is exclusive to guests staying at the hotel, offering panoramic views of Lake Michigan and the Gold Coast district. Refreshing dips and tasty poolside cocktails under the Chicago sun does not get much better. We had a fantastic 2 night stay here, so we could enjoy the pool area for several hours. It was amazing!
Also featured in:
30 Best Rooftops Bars in Chicago
In short: Located in a newly renovated Fulton Market factory, Soho House Chicago is an ideal hotel to dine, stay & relax. Soho House Chicago spans five floors and comes with a rooftop overlooking West Loop.
What we say: This rooftop pool breathes exclusivity! To have full access you must be a guest at the hotel or a Soho House member. It is definitely worth staying a night at the hotel just to enjoy this rooftop pool. As we're not members, we booked our stay here, and we weren't disappointed.
In short: Looking for a large rooftop pool in Chicago? Close to downtown and other attractions? Well, you will find this at Radisson Blu Aqua Hotel!
What we say: This rooftop pool is very convenient if you want to combine cooling off, tough strokes, close to green areas and some shopping. Here you will find all kind of amenities. The sun deck is large, and with a 25-meter lap rooftop swinning pool it makes a perfect place to start your visit in Chicago. Radisson is a well-known brand and since they can offer the largest rooftop pool in Chicago, it is on the "to-visit-list".
In short: Opened in 2019 and found in Fulton Market, the modern and urban Hoxton hotel is designed to reflect an 'open-house policy'. This concept is visible all the way from the spacious ground floor lobby to the beautiful and bright rooftop.
What we say: We had a blast when staying at this lovely hotel! Up on the top floor of the hotel, you find both a seasonal and refreshing rooftop pool, as well as a rooftop bar. As part of the several communal spaces found at the hotel, the stunning view of the Chicago skyline and the inviting swimming pool is available to all hotel guests, which makes The Hoxton a great hotel to book your hotel nights at. You don't want to miss out on this rooftop pool.
Also featured in:
30 Best Rooftops Bars in Chicago
In short: The Robey is a beautiful art-deco hotel, situated in the northwest part of town, close to Wicker Park. Up on the 6th floor of the hotel you find a lovely, seasonal Chicago rooftop pool and poolside bar.
What we say: This stylish rooftop oasis is a little slice of summer vacation in the heart of the Windy City, where you can combine refreshing swims and fantastic 180-degree views of the Chicago skyline. The triangle-shaped rooftop pool is only available to hotel gusets, but it does share space with the rooftop bar Cabana Club, available to all. So for an extra relaxing poolside hangout, head up early, before the rooftop bar opens.
In short: DoubleTree by Hilton Magnificent Mile comes with a great location in the heart of Chicago, just a short walk from the Magnificent Mile, Chicago’s #1 shopping street.
What we say: This rooftop pool is perfect after a sticky, hot day and where you can just put down your shopping bags and cool off in the hotel's newly renovated Chicago rooftop pool. Spacious and refreshing, the rooftop pool is surrounded by skyscrapers and you really get the feeling of swiming right in (or above) the bustling city. Equipped with comfy sun loungers and umbrellas, this Chicago rooftop pool and terrace is a fantastic spot to mix the city vibe with long and relaxing hours under the sun.
In short: If you want to explore Chicago in style, the aparthotel Penthouse at Grand Plaza in downtown is a very good place to start. These luxury penthouse condos and vacation rentals come with amazing views over the Chicago skyline, along with lots of amenities for recreation.
What we say: And our favorite part of this hotel, the seasonal outdoor rooftop pool, surrounded with a spacious sun deck. A place easy to spend a full day during summer, where you can swim right among the Chicago skyscrapers and relax in one of the sun loungers.
In short: Located a few blocks from the Sears Tower, Holiday Inn Hotel & Suites Chicago - Downtown is not the most luxurious option in town, but it is a great choice if you want a nice mix of comfort, location, value-for-money and some rooftop fun.
What we say: The best feature of the hotel is the seasonal outdoor rooftop swimming pool, where you can lounge and admire the cityscape for hours. Truly a blessing if the Chicago summer gets really hot. Maybe not the most luxurious and fancy rooftop pool in town. But still a good option. Up here you get more privacy than many of the more swanky pools at other hotels.
Rikard has spent the last 10 years exploring, enjoying, researching and working with rooftop venues. During these years he has visited more than 700 rooftops across the globe. The experience he has gained is used to create helpful, in-depth and accessible content, and to share his knowledge and rooftop expertise with fellow rooftop-lovers.
Browse all the cities & articles at The Rooftop Guide
Follow The Rooftop Guide