Top Cool Hotels in Chicago for an Unforgettable Stay

We checked thousands of reviews on and to find the best hotels for your stay
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Katerina Kore

Updated: 11 February 2024 · 5 min

Nestled along the shores of Lake Michigan, Chicago is a vibrant city famous for its architectural marvels, rich cultural scene, and inviting hospitality. Amidst the bustling streets and towering skyscrapers, a plethora of cool Chicago hotels awaits travelers seeking an experience that mirrors the city's spirited ambiance. These accommodations are not just places to stay; they're gateways to understanding the heart and soul of the Windy City, offering unique insights and unparalleled comfort.

Choosing the right hotel in Chicago can elevate your travel experience from ordinary to extraordinary. The coolest hotels in this dynamic city go beyond basic amenities, offering rooftop bars with stunning skyline views, curated art collections, and innovative design that reflects the creativity and diversity of Chicago itself. Whether it’s a historic hotel that tells a story or a modern boutique with cutting-edge technology, these accommodations promise a memorable stay.

For those planning a visit to Chicago, diving into the world of its cool hotels is a must. These places do more than providing a pillow to rest your head; they offer an immersive experience that can include everything from jazz evenings in a cozy lounge to gourmet dining that highlights local flavors. Let this guide introduce you to the coolest hotels in Chicago, where every stay is designed to be an integral part of your urban adventure.
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Our Top 10

(Sorted by rating & number of reviews)

1. The Palmer House Hilton
2. Viceroy Chicago Hotel
3. The Peninsula Chicago Hotel
4. The Langham Chicago Hotel
5. The Robey, Chicago, A Member Of Design Hotels
6. The Drake Hotel
7. 21C Museum Hotel Chicago
8. Hotel Lincoln
9. Chicago Athletic Association, Part Of Hyatt Hotel
10. 21C Museum Hotel Chicago

Cool Chicago Hotels with Rooftop Bars

Check Availability

Chicago
Mar 23, 2026 - Mar 24, 2026

The Palmer House Hilton

7.5

Good

(925 Reviews)

+ 216 photos
The Palmer House's claim to fame as the longest continually operating hotel in the United States speaks volumes of its historical and cultural significance in Chicago. Since its original construction in 1871 and subsequent rebuilding after the Great Chicago Fire, this hotel has been at the forefront of luxury and innovation, introducing the world to inventions like the Pina Colada and the modern-day concept of the hotel business center. Its famous Empire Room has hosted iconic entertainers, while the opulent lobby ceiling boasts a breathtaking fresco. Today, guests can enjoy modern amenities amidst this rich historical backdrop, including a luxurious spa and health club. The Palmer House seamlessly weaves the fabric of its illustrious past with the needs of contemporary travelers, offering a deeply historical yet cool Chicago hotel experience.
Address: 17 East Monroe Street
Rating: Good 7.5 (925 Reviews)
Rooms: 1641
Price: From 89$

Viceroy Chicago Hotel

9.0

Good

(1590 Reviews)

+ 168 photos
Positioned in the vibrant Gold Coast neighborhood, the Viceroy Chicago marries luxury with innovative design, crowned by its stunning rooftop bar, Devereaux. Here, guests can indulge in elegant cocktails and seasonally inspired dishes, surrounded by sleek, modern decor and panoramic views of the city's iconic skyline. The hotel's striking façade integrates seamlessly with its luxurious interior, where sophistication meets comfort. Each room is a haven of tranquility with lavish amenities, designed to offer a peaceful retreat from the bustling city. The rooftop pool offers a cooling respite during the summer months, adding an extra layer of relaxation to your stay. For those in pursuit of both architectural beauty and a lively social scene, Viceroy Chicago is a beacon among cool Chicago hotels.
Address: 1118 North State Street
Rating: Good 9.0 (1590 Reviews)
Rooms: 180
Price: From 295$

Cool Chicago Hotels with Art Galleries

Art enthusiasts and creative spirits will find solace and inspiration in this selection of cool Chicago hotels that double as art galleries. These hotels have woven art into their very fabric, showcasing collections that range from contemporary masterpieces to local and emerging artists. Walking through these hotels feels like meandering through an art exhibition, where each corridor and room presents a new visual story. They not only offer a luxurious stay but also an immersive artistic experience, inviting guests to explore and connect with art in intimate settings. Whether it’s original paintings, sculptures, or interactive installations, these accommodations provide a unique backdrop to your Chicago visit, making them unforgettable retreats for art lovers.

The Peninsula Chicago Hotel

9.4

Good

(207 Reviews)

+ 269 photos
The Peninsula Chicago is renowned for its elegance and commitment to excellence, but what sets it apart in the realm of cool Chicago hotels is its impressive art collection. Strategically placed throughout the hotel, the collection features works by established and emerging artists, with an emphasis on Asian and international pieces. Guests are treated to a visual feast, from sculptures and paintings to intricate installations. The hotel's design, echoing the sophistication of the art on display, provides a luxurious backdrop that complements the cultural experience. With its serene spa, exquisite dining options, and impeccable service, The Peninsula offers a holistic journey of comfort, cuisine, and culture. It's a sanctuary for those who appreciate the finer things in life, including the transformative power of art.
Address: 108 East Superior Street
Rating: Good 9.4 (207 Reviews)
Rooms: 257
Price: From 400$

The Langham Chicago Hotel

9.2

Good

(333 Reviews)

+ 157 photos
Set in the iconic Mies van der Rohe building, The Langham, Chicago seamlessly integrates luxury accommodations with an impressive art collection. The hotel features an array of artworks that pay homage to its architectural heritage while celebrating contemporary aesthetics. Visitors are greeted by impressive pieces in the lobby, and this artistic excellence extends throughout the hotel, enriching the environment with beauty and inspiration. The rooms and suites boast floor-to-ceiling windows, offering breathtaking views of the cityscape, complemented by tasteful art pieces that enhance the sense of serenity and sophistication. The Langham's commitment to offering a peaceful haven amidst the bustling city, along with its dedication to art, makes it one of the cool Chicago hotels for those with an eye for aesthetics and a heart for luxury.
Address: 330 North Wabash Avenue
Rating: Good 9.2 (333 Reviews)
Rooms: 316
Price: From 366$

Cool Chicago Hotels with Historic Significance

Chicago is a city steeped in history, from its illustrious architectural landmarks to its significant cultural contributions. This section highlights cool Chicago hotels that not only provide exceptional accommodations but also embody the rich history of the Windy City. These hotels have stood the test of time, each with stories that resonate with the echoes of the past. Having preserved their historical integrity while integrating modern amenities, they offer a unique stay where every room, hall, and lobby tells a tale. For travelers who yearn to immerse themselves in the authenticity and timeless charm of Chicago, these hotels stand as gateways to the past, inviting guests to experience a piece of the city's storied history.

The Robey, Chicago, A Member Of Design Hotels

8.7

Good

(362 Reviews)

+ 100 photos
The Robey stands tall, gracefully blending the past and present with its Art Deco architecture and contemporary design. Located in the bustling Wicker Park and Bucktown neighborhoods, its rooftop bar, aptly named The Up Room, offers a swanky retreat above the city. With 180-degree views of the Chicago skyline, guests can relish in artisan cocktails and small bites under the glow of the setting sun or the sparkling night sky. The hotel's facade, a striking triangular shape, ensures a picturesque city backdrop from almost every vantage point. Inside, the rooms echo the building's architectural beauty, complemented by modern amenities and minimalist décor. For those who appreciate a blend of history, design, and vibrant nightlife, The Robey captures the essence of cool Chicago hotels.
Address: 2018 W North Avenue
Rating: Good 8.7 (362 Reviews)
Rooms: 89
Price: From 144$

The Drake Hotel

7.9

Good

(574 Reviews)

+ 227 photos
The Drake, a historic hotel synonymous with luxury and elegance, has been a hallmark of Chicago hospitality since its opening on New Year’s Eve 1920. Overlooking Lake Michigan, it has hosted royalty, celebrities, and distinguished guests, secured its place in local and national culture. The opulent interiors, with their grand chandeliers and rich fabrics, transport guests to a bygone era, while the Palm Court continues to host the city’s most traditional afternoon tea. Guest rooms and suites blend vintage charm with contemporary comfort, ensuring a stay that is both nostalgic and satisfying. The Drake’s storied past and dedication to preserving its lavish early 20th-century ambiance make it a must-stay for those seeking cool Chicago hotels with historical significance.
Address: 140 East Walton Place
Rating: Good 7.9 (574 Reviews)
Rooms: 535
Price: From 133$

Cool Chicago Hotels with Innovative Design

In a city known for architectural innovation, several cool Chicago hotels push the boundaries of design, offering guests the opportunity to stay in spaces that are as visually stimulating as they are comfortable. This section showcases hotels that stand out for their architectural brilliance and interior design ingenuity. From contemporary aesthetics that challenge traditional forms to eco-friendly constructions that herald the future of sustainable travel, these establishments redefine what a hotel can be. Guests staying at these hotels can expect not just a room, but a fully immersive experience that engages the senses and sparks imagination. For the modern traveler, these hotels offer a glimpse into the future of urban accommodation.

21C Museum Hotel Chicago

8.3

Good

(1434 Reviews)

+ 97 photos
Echoing the previous mention under the art hotel category, the 21c Museum Hotel Chicago also merits inclusion for its innovative design. The building itself marries historical architecture with modern steel and glass extensions, creating a visually striking facade in the center of the city. Inside, the contemporary design of the guest rooms and public spaces—including the art museum—showcases a minimalist aesthetic that highlights the hotel’s vibrant art installations. The integration of art and design makes each stay a dynamic exploration of form, color, and texture. For those drawn to minimalist design and contemporary aesthetics, the 21c Museum Hotel is a pinnacle of innovative hotel design in Chicago.
Address: 55 East Ontario Street
Rating: Good 8.3 (1434 Reviews)
Rooms: 297
Price: From 189$

Hotel Lincoln

+ 13 photos
Nestled in the historic Lincoln Park neighborhood, Hotel Lincoln's rooftop bar, J. Parker, offers one of the most spectacular views of the city and Lake Michigan. This hotel charms with its quirky, eclectic decor that tells a story in every corner, reflecting the artistic and lively spirit of the surrounding area. Guests can enjoy craft cocktails and gourmet bites in an elegant, yet laid-back rooftop setting, making it a perfect venue for both casual gatherings and romantic evenings. The rooms are uniquely decorated, ensuring no two visits are the same, but always comfortable and inviting. Hotel Lincoln stands out for those who seek a hotel with character, warmth, and a dash of whimsy, coupled with breathtaking views that promise to enchant every guest. It’s a cornerstone among cool Chicago hotels for those who favor personality over uniformity.
Address: 1816 North Clark Street
Rooms: 184
Price: From 110$

Chicago Athletic Association, Part Of Hyatt Hotel

8.5

Good

(305 Reviews)

+ 243 photos
Housed in a Venetian Gothic landmark building, The Chicago Athletic Association Hotel reimagines the historical space into a cultural hub that blends vintage charm with modern sensibilities. The interiors, designed with a nod to the building’s athletic past, feature leather, wood, and stained glass, creating an ambiance that is both majestic and welcoming. The hotel's innovative use of its historic spaces, such as the former basketball court turned stunning ballroom, exemplifies a commitment to preserving the past while embracing contemporary design. The rooftop bar and restaurant offer unmatched views of Millennium Park and Lake Michigan, adding a layer of modern luxury to the stay. For enthusiasts of architecture and design, this hotel provides an inspiring stay amidst one of Chicago’s most creatively repurposed spaces.
Address: 12 South Michigan Avenue
Rating: Good 8.5 (305 Reviews)
Rooms: 241
Price: From 232$

21C Museum Hotel Chicago

8.3

Good

(1434 Reviews)

+ 97 photos
21C Museum Hotel Chicago is not just a hotel; it’s an innovative fusion of art museum and boutique accommodation. Housed in a historic building, it features rotating exhibitions of contemporary art throughout its public spaces and a dedicated museum space that's open to the public. Each guest room is carefully designed as a minimalist backdrop to highlight the original artwork displayed within. Beyond merely a place to stay, 21c invites its guests to engage with thought-provoking works, making it a dynamic cultural hub. Workshops, artist talks, and curated events are regularly hosted, enriching the stay of each guest with deep dives into the creative process. For travelers who seek an immersive artistic journey, this hotel stands as a pinnacle among cool Chicago hotels, blending luxury with the vibrancy of contemporary art culture.
Address: 55 East Ontario Street
Rating: Good 8.3 (1434 Reviews)
Rooms: 297
Price: From 189$