Chicago, the vibrant city known for its architectural marvels and bustling streets, offers a unique blend of urban excitement and relaxation. For travelers seeking an elevated experience, exploring Chicago hotels with outdoor rooftop pools adds a touch of luxury and indulgence to your stay. These rooftop pools not only provide a refreshing escape from the urban hustle but also offer panoramic views of the stunning city skyline and Lake Michigan.
Immerse yourself in the beauty of Chicago's architecture and skyline as you unwind by the outdoor rooftop pools of select hotels in the city. From soaking up the sun during the day to enjoying a soothing evening swim under the starlit sky, these rooftop oases provide a serene retreat amidst the bustling city below. Whether you're looking to cool off after a day of exploration or simply relax with a cocktail in hand, these rooftop pools offer a one-of-a-kind experience that enhances your Chicago getaway.
Indulge in the ultimate Chicago staycation by booking a room at one of the city's top hotels with outdoor rooftop pools. Whether you're a local looking for a weekend escape or a visitor seeking a memorable stay, these luxurious accommodations offer a perfect blend of comfort, style, and unforgettable views. Discover the allure of rooftop poolside relaxation in the very heart of the Windy City and elevate your Chicago experience to new heights.
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Our Top 10
(Sorted by rating & number of reviews)
1.
The Drake Hotel
2.
Chicago Athletic Association, Part Of Hyatt
3.
The Robey, Chicago, A Member Of Design Hotels
4.
The Publishing House Bed And Breakfast
5.
The Peninsula Chicago
6.
The Gwen, A Luxury Collection Hotel, Michigan Avenue Chicago
7.
Hotel Emc2, Autograph Collection
8.
Londonhouse Chicago, Curio Collection By Hilton
9.
Viceroy Chicago
10.
The Langham Chicago
Luxury Retreats with Chicago Hotels with Outdoor Rooftop Pools
Check Availability
Chicago
May 25, 2026 - May 26, 2026
The Drake Hotel
+ 91 photos
Experience the timeless charm and grandeur of The Drake, a Hilton Hotel, an iconic institution in Chicago known for its historic elegance and unparalleled hospitality. The hotel's outdoor rooftop pool provides a tranquil escape with breathtaking views of Lake Michigan, offering a serene oasis amidst the bustling cityscape. Immerse yourself in the classic luxury and sophistication of The Drake, where tradition meets modern comfort to create an unforgettable stay that embodies the essence of Chicago's historic hospitality.
Address:
140 East Walton Place
Rating:
Good
8.5
(629 Reviews)
Rooms:
534
Price:
From 248$
Luxury Retreats with Chicago Hotels with Outdoor Rooftop Pools
Chicago Athletic Association, Part Of Hyatt
+ 91 photos
Step into a bygone era of elegance and sophistication at The Chicago Athletic Association Hotel, a historic landmark in the very heart of downtown Chicago. The hotel's rooftop pool, located atop the iconic building, offers panoramic views of Millennium Park and the city skyline, creating a picturesque setting for relaxation and enjoyment. Delve into the hotel's rich heritage and architectural splendor, where classical design, personalized service, and modern amenities converge to offer a truly unforgettable Chicago experience.
Address:
12 South Michigan Avenue
Rating:
Good
8.4
(229 Reviews)
Rooms:
240
Price:
From 252$
The Robey, Chicago, A Member Of Design Hotels
+ 91 photos
Experience the epitome of urban chic at The Robey, a boutique hotel located in the very heart of Chicago's vibrant Wicker Park neighborhood. The hotel's rooftop pool boasts panoramic views of the city skyline, creating a stylish setting for relaxation and socializing. Embrace the hip and artistic vibe of The Robey, with its sleek design, modern amenities, and lively atmosphere that perfectly captures the essence of Chicago's dynamic cultural scene.
Address:
2018 W North Avenue
Rating:
Good
8.8
(249 Reviews)
Rooms:
90
Price:
From 144$
The Publishing House Bed And Breakfast
+ 91 photos
Experience a cozy and intimate stay at The Publishing House Bed and Breakfast, a boutique hotel located in the vibrant West Loop neighborhood. This historic property exudes charm and warmth, offering personalized service and thoughtful amenities that create a home-like atmosphere for guests. Relax by the hotel's outdoor rooftop pool, a hidden oasis in the city, and enjoy the tranquility and comfort of this unique bed and breakfast that captures the essence of Chicago's boutique hospitality.
Address:
108 N May Street
Rating:
Good
9.4
(39 Reviews)
Rooms:
11
Price:
From 260$
The Peninsula Chicago
+ 91 photos
Experience unparalleled luxury at The Peninsula Chicago, featuring a stunning outdoor rooftop pool offering panoramic views of the city skyline. This prestigious hotel blends timeless elegance with modern sophistication, providing guests with a truly opulent retreat in the lively heart of downtown Chicago. Pamper yourself with personalized service, exquisite dining options, and indulgent spa treatments, all while enjoying the serene ambiance of the rooftop pool oasis.
Address:
108 East Superior Street
Rating:
Good
9.4
(239 Reviews)
Rooms:
317
Price:
From 337$
The Gwen, A Luxury Collection Hotel, Michigan Avenue Chicago
+ 91 photos
Discover a hidden gem in the lively heart of the Magnificent Mile at The Gwen, a Luxury Collection Hotel, where boutique charm meets modern luxury. The hotel's outdoor rooftop pool offers a serene escape with sweeping views of the city skyline, providing a peaceful oasis amidst the bustling urban landscape. Immerse yourself in the hotel's sophisticated ambiance, exquisite design, and personalized service, all of which reflect the unique character and charm of this elegant Chicago retreat.
Address:
521 North Rush Street
Rating:
Good
8.7
(84 Reviews)
Rooms:
10
Price:
From 131$
Hotel Emc2, Autograph Collection
+ 78 photos
Step into a world of artistic elegance at Hotel EMC2, Autograph Collection, renowned for its innovative design and sophisticated style. The hotel's outdoor rooftop pool is a hidden gem in the city, offering a tranquil escape with sweeping views of Chicago's iconic architecture. Immerse yourself in the blend of science and art that defines this unique hotel, where every detail is thoughtfully curated to provide a truly exceptional stay for discerning guests.
Address:
228 East Ontario Street
Rating:
Good
8.7
(303 Reviews)
Rooms:
34
Price:
From 204$
Londonhouse Chicago, Curio Collection By Hilton
+ 91 photos
Discover a blend of historic elegance and modern luxury at LondonHouse Chicago by Hilton, a landmark hotel located along the Chicago River. The hotel's rooftop pool offers stunning views of the city and Lake Michigan, providing a captivating backdrop for relaxation and rejuvenation. Immerse yourself in the rich history and grandeur of LondonHouse, where timeless design, exceptional service, and unparalleled hospitality create a sense of timeless elegance that embodies the spirit of Chicago.
Address:
85 E Wacker Drive
Rating:
Good
8.8
(773 Reviews)
Rooms:
448
Price:
From 361$
Viceroy Chicago
+ 91 photos
Experience contemporary luxury at Viceroy Chicago, a sophisticated hotel epitomizing modern elegance and urban refinement. The hotel's outdoor rooftop pool provides a stylish escape with stunning views of the city and Lake Michigan, offering a serene setting for relaxation and socializing. Immerse yourself in the chic atmosphere of Viceroy Chicago, where exceptional service, upscale amenities, and exquisite design combine to create a truly unforgettable Chicago experience.
Address:
1118 North State Street
Rating:
Good
8.9
(1011 Reviews)
Rooms:
179
Price:
From 215$
The Langham Chicago
+ 91 photos
Elevate your Chicago experience at The Langham, a luxurious hotel renowned for its impeccable service and elegant design. The hotel's outdoor rooftop pool overlooks the Chicago River, creating a serene setting for relaxation and rejuvenation. Indulge in the Langham's legendary hospitality, exquisite culinary offerings, and opulent accommodations, all while enjoying the unparalleled views from the rooftop pool deck.
Address:
330 North Wabash Avenue
Rating:
Good
9.4
(334 Reviews)
Rooms:
316
Price:
From 661$