Unveiling the 31 Best Hotels in Chicago, From West Loop to Magnificent Mile

Post originally Published March 3, 2024 || Last Updated March 4, 2024

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Unveiling the 31 Best Hotels in Chicago, From West Loop to Magnificent Mile - Luxury on the Magnificent Mile: Top High-End Options Along Michigan Avenue


Unveiling the 31 Best Hotels in Chicago, From West Loop to Magnificent Mile

If you're looking to indulge in some serious luxury during your stay in Chicago, look no further than the Magnificent Mile. This famous stretch along Michigan Avenue is home to some of the city's most elegant and upscale hotels, perfect for those who want to treat themselves to the highest levels of service and amenities.

The Langham tops many lists as Chicago's most opulent place to lay your head. This 316-room property oozes sophistication, from the Chuan Spa to the Zen-inspired Pavilion lounge to the Michelin-starred Travelle restaurant. Guests rave about the over-the-top pampering, including nightly turndown service and complimentary shoe shines. The generously sized, richly appointed rooms provide soothing comforts like soaking tubs and views over the Chicago River.

For old-world extravagance, the Drake Hotel has been a standout since 1920. Ornate chandeliers, Italian marble, and oak paneling transport you back in time. The Cape Cod and Lake Shore Drive rooms offer scenic vistas. Dine on contemporary French cuisine at Café on Oak or classic afternoon tea service in the Palm Court. Work out in the state-of-the-art fitness center, then unwind in the Magnificent Mile Spa. Personalized butler service is available for ultimate indulgence.
The Peninsula Chicago is lauded as one of the country's top urban resorts. Guests feel pampered from check-in onwards with complimentary airport transfers in a house Rolls-Royce and personal hosts to cater to every need. The property's Hong Kong heritage shines through in its East-meets-West design. Relax in the 20,000-square-foot spa and health club or the stunning indoor pool, then dine on exquisite Cantonese dishes at Zest. The lavish suites feel like private residences.

For a contemporary twist, check into the Viceroy Chicago. Sleek, modern décor with floor-to-ceiling windows creates a vibe that's both sophisticated and energetic. Kick back in your urban retreat-like room or suite with a soak tub, then head up to the rooftop pool deck for jaw-dropping city views. Three dining venues, including a scenic rooftop lounge, and a stylish FIT workout facility round out the offerings. It's luxe living in the heart of the action.
Of course, no discussion of Mag Mile luxury would be complete without mentioning the legendary Four Seasons. Expect legendary service and endless amenities like twice-daily housekeeping and nightly turndown. Rooms are spacious and sumptuous, some offering views of Lake Michigan. Dine at the Michelin-starred Allium or unwind at the spa. If you're seeking the ultimate in pampering and prestige, the Four Seasons hits every note.

What else is in this post?

  1. Unveiling the 31 Best Hotels in Chicago, From West Loop to Magnificent Mile - Luxury on the Magnificent Mile: Top High-End Options Along Michigan Avenue
  2. Unveiling the 31 Best Hotels in Chicago, From West Loop to Magnificent Mile - Historic Flair in the Loop: Landmark Buildings Turned Luxury Lodging
  3. Unveiling the 31 Best Hotels in Chicago, From West Loop to Magnificent Mile - Waterfront Indulgence: Relaxing Hotels with Lake Michigan Views
  4. Unveiling the 31 Best Hotels in Chicago, From West Loop to Magnificent Mile - Sky-High Accommodations: Rooftop Pools and Pool Decks with Panoramas
  5. Unveiling the 31 Best Hotels in Chicago, From West Loop to Magnificent Mile - Neighborhood Gems Off the Beaten Path: Hidden Treasures in Logan Square and Gold Coast

Unveiling the 31 Best Hotels in Chicago, From West Loop to Magnificent Mile - Historic Flair in the Loop: Landmark Buildings Turned Luxury Lodging


In the bustling heart of Chicago's downtown area, known as the Loop, lies a treasure trove of historic buildings that have been transformed into luxurious hotels. These landmarks not only offer a glimpse into the city's rich history but also provide an unparalleled experience of elegance and grandeur. Staying in one of these iconic establishments allows guests to immerse themselves in the timeless charm of Chicago while indulging in top-notch amenities and services.
One such remarkable hotel is The Palmer House, a Hilton Hotel. As the longest continuously operating hotel in North America, The Palmer House exudes a sense of grandeur that is hard to replicate. Stepping into the opulent lobby, adorned with crystal chandeliers and intricate frescoes, transports guests to a bygone era of elegance. The hotel offers a range of luxurious rooms and suites, each meticulously designed to provide the utmost comfort and style. With amenities like a full-service spa, a fitness center, and multiple dining options, including the famed Lockwood Restaurant, The Palmer House promises an unforgettable stay.
Another iconic landmark that has been transformed into a luxury hotel is The Chicago Athletic Association Hotel. Originally built as a private athletic club in 1893, this historic building has been lovingly restored to its former glory. The hotel seamlessly blends old-world charm with modern comforts, offering guests a unique and memorable experience. The beautifully appointed guest rooms feature a blend of vintage and contemporary furnishings, creating an atmosphere of timeless sophistication. The hotel's rooftop bar, Cindy's, offers breathtaking views of Millennium Park and Lake Michigan, making it the perfect spot to unwind and enjoy a handcrafted cocktail.
For those seeking a truly immersive historic experience, The LondonHouse Chicago is a must-visit. Housed in a historic Beaux-Arts building, this luxury hotel offers unparalleled views of the Chicago River and the iconic Michigan Avenue Bridge. The meticulously restored interiors seamlessly blend classic elegance with modern design elements. Each room and suite is thoughtfully designed to provide the utmost comfort and sophistication. The hotel's rooftop bar, LH, offers panoramic views of the city skyline, providing a memorable setting for enjoying a drink and taking in the breathtaking surroundings.
Guests who have had the pleasure of staying in these historic landmarks-turned-luxury hotels rave about the unique experiences they offer. They appreciate the attention to detail in the restoration of the buildings, which allows them to truly appreciate the architectural beauty and historical significance. The seamless integration of modern amenities and services ensures that guests can enjoy the best of both worlds – the charm of the past and the comforts of the present.
Many guests also praise the exceptional service provided by the staff, who go above and beyond to ensure a memorable stay. From personalized recommendations for exploring the city to attentive and prompt assistance, the staff's dedication to creating a truly unforgettable experience sets these hotels apart.
Exploring the historic flair in the Loop is not just about staying in luxurious lodgings; it's about immersing oneself in the rich history and architectural beauty that Chicago has to offer. Whether it's marveling at the intricate details of the buildings' facades or discovering hidden gems within, these landmark hotels provide a gateway to a bygone era while offering all the modern comforts and luxuries one could desire.

Unveiling the 31 Best Hotels in Chicago, From West Loop to Magnificent Mile - Waterfront Indulgence: Relaxing Hotels with Lake Michigan Views


For travelers seeking the ultimate in relaxation and indulgence, Chicago’s lakefront hotels offer a serene escape with breathtaking vistas of Lake Michigan. Though nestled in the heart of a bustling metropolis, these urban sanctuaries transport guests to a whole different world with their tranquil ambiance and aquatic scenery.

The Langham Chicago is renowned for its lavish accommodations and pampering amenities, made even more enticing by its prime waterfront location. Floor-to-ceiling windows perfectly frame the glittering lake, cityscape, and Chicago River, creating a dramatic backdrop. After a day exploring The Loop, return to your luxuriously appointed room or suite to soak in the freestanding tub while drinking in the views. Later, unwind lakeside on the private terrace with a cocktail from the honor bar as the sun sets.

Equally alluring is The Peninsula Chicago, lauded as one of the nation’s finest five-star properties. Here you’ll find sophisticated rooms with mood lighting and soaking tubs to promote relaxation. Savor creative Cantonese cuisine at Zest with romantic vistas of the Chicago River merging with the lake. Guests particularly praise the spa’s indulgent massages and treatments coupled with serene waterfront views visible through floor-to-ceiling glass walls. The majestic pool, evoking an Italian seaside resort, is another haven for escaping the bustling city.
Thompson Chicago also entices with sleek, nautically-inspired rooms overlooking Lake Michigan. Dip into the picturesque rooftop pool to feel worlds away while still in the heart of the city. Tuck into Mediterranean flavors at The Florentine’s riverfront patio, then cap off your evening with creative cocktails at the retro Up Room lounge, where floor-to-ceiling windows showcase glittering skyline reflections on the water.

Hotel EMC2 radiates a hip, modern vibe, while also pampering guests with splendid lakefront views. Unwind in your urban oasis accented with glimpses of shimmering blue. Embark on a culinary journey at Travelle Kitchen + Bar overlooking the Marina, with seasonal dishes fusing global elements. Later ascend to the GEMS rooftop lounge to soak in skyscraper panoramas framed by waterfront sunsets in the distance.

Unveiling the 31 Best Hotels in Chicago, From West Loop to Magnificent Mile - Sky-High Accommodations: Rooftop Pools and Pool Decks with Panoramas


Chicago takes relaxation and recreation to new heights with an array of hotels boasting rooftop pools and deck spaces that open up the skies. After immersing yourself in big city sights and sounds, ascending to these elevated oases offers a refreshing perspective with open-air facilities, infinity pool vibes, and sweeping urban panoramas.

The Hampton Inn Chicago Downtown / N Loop / Michigan Ave entices guests skyward with its heated indoor/outdoor pool. Floor-to-ceiling glass walls allow you to soak in scenic views of the Willis Tower and Chicago River from the warmth of the interior pool in colder months. Come summer, the retractable roof opens to bring an alfresco resort experience to the heart of downtown. Chaise lounges lining the deck provide prime spots for sunbathing with vistas of the cityscape all around you.
Thompson Chicago sets the stage for scenic relaxation at its chic rooftop pool and lounge space overlooking Lake Michigan. Gaze out at sailboats bobbing in the harbor and Lake Shore Drive hugging the shimmering waterfront from plush poolside cabanas. The intimate, infinity edge pool makes it feel like you're floating atop the glittering skyline, while private cabanas allow for secluded relaxation.

The Robey Chicago also thrills with its best-in-class outdoor escape. Ascend to the retractable roof deck on the 12th floor for swim sessions in the 25-yard lap pool set against a backdrop of the Chicago skyline. Spread out on lounge chairs or daybeds and soak up sunshine and panoramas of surrounding skyscrapers. Come evening, the space transitions into an alfresco lounge with DJ beats and craft cocktails beneath the stars.
Kimpton Hotel Monaco Chicago tempts guests to the 14th floor to access its seasonal, heated saltwater pool. Frameless glass walls surround the deck, blurring the lines between indoor and outdoor space. From the water, take in 180-degree views spanning iconic skyscrapers, Lake Michigan, and Navy Pier. Cabanas and chic furnishings like hanging egg chairs heighten the urban oasis ambiance.

Unveiling the 31 Best Hotels in Chicago, From West Loop to Magnificent Mile - Neighborhood Gems Off the Beaten Path: Hidden Treasures in Logan Square and Gold Coast


While many visitors to Chicago seek out lodgings along the bustling Magnificent Mile or in the heart of downtown, some of the city's most charming accommodations can be found in lesser-explored neighborhoods just awaiting discovery. Nestled amongst charming boutiques, cafes and cultural attractions inareas like Logan Square and Gold Coast lie hidden hotel gems imbued with local flair and character.

Northwest of downtown near Downtown Armitage station sits The Robey, a trendy boutique known for its art installations, rooftop pool with sweeping skyline views and clever nods to the building's past life as a high school. The vintage brick architecture and reclaimed wood accents throughout the industrial chic interiors conjure nostalgia while avoiding kitsch. Guests appreciate the upbeat yet unpretentious atmosphere and convenient access to neighborhood hotspots. "It's like staying in your friend's super cool loft in Brooklyn but you're still in the middle of Chicago," remarked one traveler from New York.
Also buzzing with creative energy a few miles northwest is Logan Square and the LOCAL Chicago. Originally a motor inn, this hybrid hotel underwent a transformation blending retro elements with modern conveniences. Vintage mid-century furnishings paired with amenities like smart TVs keep the past present without sacrificing comfort. Locals frequent the café and rooftop bar, drawing guests to mingle with residents and soak up the neighborhood character. "You really get a sense of the artistic vibe and local culture staying here," noted one visitor from Seattle.

For those desiring charm alongside Chicago's famous lakeshore, consider Hotel Lincoln, nestled in the affluent Gold Coast. The luxury boutique hotel fills its intimate space with captivating artworks and touches of art deco glamor. All the while, guests can enjoy privileges at the prestigious Chicago Athletic Club next door. "It's like having an urban resort all to yourself - intimately scaled but with all the services of a larger property. A hidden gem," remarked a guest from London.

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