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A dramatic, ever-changing skyline silhouetted against endless skies over Lake Michigan, Chicago is a sight to be seen. Instantly-recognizable historic landmarks include the Chicago Water Tower and the Holy Name Cathedral, while modern skyscrapers include the John Hancock Center and Willis Tower. Chicago isn't just renowned as the birthplace of skyscrapers, however. A world-class city with a long and colorful history, Chicago has numerous high-end shopping outlets, a cutting-edge culinary scene, vibrant nightlife, and cultural attractions left and right. With some of the city's finest hotels taking on the form of soaring skyscrapers, guests will find an abundance of spectacular vistas. Our favorites below.
Best Overall: The Peninsula Chicago
Gazing down upon the designer shopping boutiques, restaurants, and art galleries of the famed Magnificent Mile, the Peninsula Chicago places guests in the epicenter of downtown Chicago. Styling itself as the place where Far Eastern graciousness and Midwestern hospitality meet, the hotel is consistently rated one of the finest properties in the U.S. and it's renowned for its graceful architecture, impeccable contemporary decor, and attentive customer service. Sumptuous guestrooms offer a variety of city panoramas and come with a relaxed blue and white color scheme punctuated with exclusively-commissioned art pieces. Rooms have marble bathrooms with an LCD TV set above the soaking tub. Some of the best views can be found on the alfresco lounge of the rooftop Z Bar, where guests can gaze down the length of N Michigan Avenue towards the historic Chicago Water Tower, John Hancock Building, and other famous landmarks. Views can also be enjoyed from the indoor pool and Jacuzzi tub, housed in a grand hall with full-length windows.
Best Budget: The ACME Hotel Company
The site of the ACME Hotel Company was once known as a Prohibition-era gangster hangout, but nowadays, the spot has been reborn as a retro, rock ‘n roll-themed boutique. Though guests can certainly enjoy great views of the surrounding River North neighborhood, many of the best sights are that of the quirky art installations scattered throughout the premises. Although small, rooms are packed full of modern amenities, including a flat-screen TV and a high-tech sound system, and come with excellent services such as a freshly-made coffee in the mornings and a ‘knock and drop’ meal delivery service. The Berkshire Room offers a nod to the past with a Prohibition-themed bar serving classic cocktails and cold beers, while the Bunny Slope is an apres-ski-inspired space with a hot tub, LED TV, and drink service that can be privately booked. Located in central Chicago, the hotel provides close proximity to numerous attractions and excellent transportation connections to many others.
Best Location: The Gwen, A Luxury Collection Hotel
Located in the heart of downtown Chicago, the Gwen offers ease of access to the Windy City's most attractive sights. The storied shops of the Magnificent Mile are found scattered along the length of N Michigan Avenue to the north, while countless restaurants, bars, and cocktail lounges are found along the streets of the River North district to the east. A short walk south, the iconic DuSable Bridge crosses the Chicago River, where guests can follow a scenic path to the shores of Lake Michigan. A stylish and contemporary hotel designed in glam Art Deco style, guests will find comfortable rooms furnished with tasteful, luxurious fittings, flat-screen TVs, and bathrooms with separate bathtubs and showers. The rooftop terrace provides guests with a scenic backdrop while they dine at low-set tables inlaid with blazing gas firepits.
Best for Families: Four Seasons Hotel Chicago
Set atop the shops and restaurants of the upscale 900 North Michigan mall, the Four Seasons Hotel Chicago offers stylish accommodation suitable for families with kids of all ages. The hotel offers youngster-friendly in-room amenities, a complimentary gift upon check-in, and babysitting services should parents want to go out on the town. Guestrooms and suites offer a variety of views, contain classic décor with contemporary highlights, and can accommodate a range of family sizes. Guests of all ages will love indulging in custom-made sundaes which are served from an ice cream cart wheeled directly to their door. A Roman-inspired hall houses a large indoor pool and adjacent hot tub; life jackets and swim noodles are available for young ones. The colorful kids’ club comes with comfy beanbags, toys, and activities for younger children, as well as foosball and air hockey tables for preteens. Fresh seasonal fare is available at onsite Allium, but guests can also choose to dine in courtesy of an extensive room service menu that includes children's’ meals and dessert.
Best for Couples: The Langham Chicago
Set on the banks of the Chicago River, the Langham is a stunning contemporary property that offers unbeatable proximity to the restaurants in River North and shops on nearby Magnificent Mile. The hotel is considered one of the finest luxury stays in the U.S. — and it provides guests with every indulgence. Breathtaking views are to be found in guestrooms where floor-to-ceiling windows meet contemporary furnishings, modern amenities, and bathrooms with soaking tubs, separate glass showers, and marble accents. Of course, the hotel hosts an enviable spa, and the centerpiece there is an enchanting indoor pool where hundreds of star-like spotlights reflect off the water to create a magical ambiance. Other facilities include hydrotherapy Jacuzzi tubs, a Himalayan salt stone sauna, Oriental steam rooms, and aromatherapy showers. You can arrange for a massage or health and beauty treatments which are inspired by ancient Chinese practices. The Travelle restaurant provides seasonal American fare in a casual yet intimate atmosphere, with a glass-enclosed kitchen providing an unforgettable culinary spectacle.
Best for Luxury: Waldorf Astoria Chicago
Rubbing shoulders with the grand Victorian townhouses, boutique shops, red hot restaurants, and lively bars of the Gold Coast neighborhood, the Waldorf Astoria is one of Chicago's most high-end stays. Rooms and suites come with stylish, retrained furnishings and a sophisticated palette of grey and beige. In-room amenities include a flat-screen TV, iPod dock and surround sound system, and indulgent extras such as a marble fireplace and private terrace. Marble-lined bathrooms come with a walk-in shower, dual vanity, and luxurious soaking tub with a TV screen set above for bath-time viewing. The award-winning spa provides a full range of massage, facial, and body treatments, which can also be enjoyed in the privacy of guests’ accommodations. Renowned chef Michael Mina provides an elegant French dining experience amid polished wood and chrome fittings in the Margeaux Brasserie restaurant. Meanwhile, a casual patisserie in the lobby that serves fresh pastries, coffee, and handcrafted cocktails.
Best for Lake View: W Chicago – Lakeshore
With just the scenic North Lake Shore Drive separating the W Chicago from Lake Michigan, rooms and common areas in this modern, upscale hotel offer uninterrupted panoramas of the natural attraction. The view also encompasses the sandy Ohio Street Beach and the lawns, trees, and walkways of Milton Lee Olive Park, which are easily accessible via a short walk along the Lakefront Trail. The most primo lake views can be enjoyed from the rooftop terrace, where guests can sit on cushioned couches and at high-top tables while sipping wines, cocktails, and other adult beverages from the adjacent glass-enclosed bar. Guestrooms offer the choice of city or lake views and come retro furniture, modern amenities, and a work desk. Bathrooms have a walk-in shower and Bliss toiletries, so you won't have to pack all of your own. Lake views can also be found in the private treatment rooms of the Bliss Spa and from the stylish dining room of the CURRENT restaurant if you just can't get enough.
Best for Business: Fairmont Chicago
Surrounded on three sides by green city parks, views at the Fairmont Chicago encompass the lake, the Chicago River, and the downtown skyline. With 14 meeting spaces ranging from intimate boardrooms to grand ballrooms with a capacity for 2,000 guests, the hotel is capable of hosting team development training, conferences, and seminars. The hotel has partnered with a leading conference services provider to ensure the latest and best audio-visual equipment is professionally installed and operated to maximum effect. Scenic guest rooms and suites are comfortably outfitted with contemporary furnishings and come with amenities such as a work desk, phone, and Wi-Fi to keep guests connected and productive. A business center provides printing, copying, fax, and mail services. After a productive day, guests can work up a sweat at the fitness center followed by a massage or body treatment at the spa. Columbus Tap provides gastropub food and drinks, while The Bar offers small bites, cocktails, and a comprehensive wine selection.
Best Rooftop: The Ritz-Carlton Chicago
With a premium location on the Magnificent Mile, the Ritz-Carlton Chicago offers a range of both city and lake views as well as unbeatable access to shopping malls, historic landmarks, and the Museum of Contemporary Art. Undoubtedly, the property's highlight is the rooftop terrace lounge of the Torali restaurant. A cozy and intimate space, guests can relax on plush cushioned couches scattered around a marble fireplace while snacking on Mediterranean bites and sipping premium spirits, international wines, and specialty cocktails. Guestrooms, suites, and apartments are furnished with classic dark wood furniture which is complemented by soft grey fittings and come with a choice of city or lake views. Excellent views are also available through the glass walls and ceiling of the greenhouse-inspired café, a stylish space with polished marble fittings and graced by verdant olive trees. A full-service spa provides massage, health, and beauty treatments, and a fitness center contains both modern equipment and stunning lake views.