Best Hotels with Rooftop Pools in Chicago

We checked thousands of reviews on and to find the best hotels for your stay
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Alexandra Sanders

Updated: 31 July 2024 · 2 min

Nestled amid the iconic skyline of the Windy City lies a hidden gem that elevates the Chicago experience to new heights - hotels with rooftop pools. Imagine sipping a refreshing cocktail while soaking in panoramic views of the bustling city below, all within the luxurious confines of a rooftop oasis. Chicago's vibrant hospitality scene boasts a curated selection of hotels that offer this coveted amenity, catering to discerning travelers seeking both relaxation and sophistication during their stay.

From the trendy River North district to the historic Loop neighborhood, hotels with rooftop pools in Chicago are strategically located to provide guests with unparalleled access to the city's top attractions and cultural landmarks. Whether you're in town for a romantic getaway, a business trip, or a fun-filled vacation with friends, these elevated retreats offer the perfect combination of convenience and indulgence. Embrace the allure of the Chicago skyline as you bask in the sun-drenched serenity of a rooftop pool, creating unforgettable memories against the backdrop of the city's architectural wonders.

Indulge in the epitome of urban luxury as you immerse yourself in the opulent ambiance of Chicago's hotels with rooftop pools, where every moment is a celebration of sophistication and style. Unwind in plush cabanas, take a refreshing dip in the crystalline waters, or simply marvel at the breathtaking vistas that stretch as far as the eye can see. Whether you're unwinding after a day of exploration or seeking a tranquil retreat from the bustling city below, these rooftop pools redefine the concept of luxury hospitality in the lively heart of Chicago.
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Our Top 4

(Sorted by rating & number of reviews)

1. The Gwen, A Luxury Collection Hotel, Michigan Avenue Chicago
2. The Robey, Chicago, A Member Of Design Hotels
3. Londonhouse Chicago, Curio Collection By Hilton
4. Viceroy Chicago

Hotels with Rooftop Pools Chicago

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Chicago
Jun 16, 2026 - Jun 17, 2026

The Gwen, A Luxury Collection Hotel, Michigan Avenue Chicago

8.7

Good

(84 Reviews)

+ 91 photos
The Gwen stands as a beacon of modern elegance, boasting a rooftop pool that affords sweeping views of the city skyline, creating the perfect setting for relaxation and rejuvenation. Guests can unwind in chic cabanas, sip artisanal cocktails, and bask in the sun-kissed ambiance that epitomizes the quintessential rooftop pool experience in Chicago. With luxurious accommodations, impeccable service, and a prime location near Magnificent Mile, The Gwen offers a truly immersive and unforgettable stay that showcases the best of Chicago hospitality.
Address: 521 North Rush Street
Rating: Good 8.7 (84 Reviews)
Rooms: 10
Price: From 131$

Hotels with Rooftop Pools Chicago

The Robey, Chicago, A Member Of Design Hotels

8.8

Good

(249 Reviews)

+ 91 photos
Nestled in the vibrant Wicker Park neighborhood, The Robey boasts a rooftop pool that embodies a chic and cosmopolitan atmosphere, reflecting the trendy and artistic spirit of Chicago's northwest side. Guests can enjoy cocktails at the Up Room, a stylish rooftop bar adjacent to the pool, while taking in the stunning views of the city skyline and beyond. The Robey's rooftop pool offers a unique blend of relaxation and urban sophistication, making it a coveted destination for discerning travelers seeking a distinctive Chicago experience.
Address: 2018 W North Avenue
Rating: Good 8.8 (249 Reviews)
Rooms: 90
Price: From 144$

Londonhouse Chicago, Curio Collection By Hilton

8.8

Good

(773 Reviews)

+ 91 photos
Perched atop the iconic LondonHouse Chicago, the rooftop pool beckons guests to indulge in a 360-degree panorama of the cityscape, providing an exclusive retreat in the lively heart of downtown Chicago. This historic hotel seamlessly marries old-world charm with contemporary luxury, offering a rooftop pool experience that is both timeless and trendsetting. Immerse yourself in the epitome of urban sophistication at LondonHouse Chicago, where every moment is a celebration of style, comfort, and panoramic views that capture the essence of Chicago's skyline.
Address: 85 E Wacker Drive
Rating: Good 8.8 (773 Reviews)
Rooms: 448
Price: From 361$

Viceroy Chicago

8.9

Good

(1011 Reviews)

+ 91 photos
Located in the bustling Gold Coast neighborhood, Viceroy Chicago offers a rooftop pool oasis that exudes contemporary elegance and understated luxury, providing a tranquil escape from the urban hustle below. Guests can unwind in plush loungers, enjoy craft cocktails at the rooftop bar, and immerse themselves in the serene ambiance that characterizes this sophisticated retreat. With its impeccable design, personalized service, and panoramic views of Lake Michigan, Viceroy Chicago epitomizes the chic urban escape, showcasing the allure of rooftop pool living in the center of the city.
Address: 1118 North State Street
Rating: Good 8.9 (1011 Reviews)
Rooms: 179
Price: From 215$