Welcome to the Windy City, where you’ll wander through streets under towering skyscrapers and sample the best deep-dish pizza in the nation. Visit Magnificent Mile on Michigan Avenue, which is lined with hundreds of shops, panoramic views from a ferris wheel, live performances, museums and boat cruises. You’ll have to make a stop at the Loop and travel down the Chicago Riverwalk, as well as visit the lakefront to take a picture in front of the well-known Cloud Gate mirror sculpture, also known as “The Bean.” Theater fans will love having a front-row seat to Tony award-winning plays. When you think of Chicago, your mind likely goes to the skyscrapers, but along the Gold Coast are miles of sand lining Lake Michigan, so you can sunbathe and swim alongside city views. Feel prepared for a fun day ahead in Chicago when you stay at one of these luxurious hotels.
Subscribe to Observer’s Lifestyle Newsletter
High-End Chicago Hotels
Waldorf Astoria Chicago
When it’s time to check-in at Waldorf Astoria Chicago, you’ll feel like you pulled up to a French chateau in the middle of the Gold Coast district. The stunning entrance to the downtown Chicago hotel showcases its status as one of the best luxury hotels in the city. The spacious guest rooms are modern and tranquil retreats with large wet bars, marble bathrooms and individual showers and soaking tubs. The pet-friendly hotel has free WiFi, room service, a fitness center and an indoor pool for year-round swimming. When it’s time to unwind, visit the on-site spa that features a whirlpool, steam room and sauna. The family-friendly spa services extend to in-room treatments like manicures and pedicures for kids. Ask the concierge to make you a reservation at the all-day restaurant that serves a combination of French and American cuisines with a Chicago influence. The Waldorf Astoria Chicago has a prime location just off of Miracle Mile near the Lake Michigan waterfront and Gold Coast beaches.
Sofitel Chicago Magnificent Mile
At Sofitel Chicago Magnificent Mile, you’re immersed in everything Chicago has to offer near the bustling Michigan Avenue. The five-star downtown hotel has cozy rooms with beautiful city views filled with skyscrapers. The larger guest rooms offer separate living areas and a pillow menu so you can customize your comfort. The luxe accommodation in the Gold Coast neighborhood has an on-site French restaurant with floor-to-ceiling windows and an elegant bar with a library. Guests of the Magnificent Mile hotel enjoy the fitness center and views of Lake Michigan and downtown Chicago.
Four Seasons Hotel Chicago
This downtown Chicago Four Seasons is part of a well-known chain of luxury hotels and offers easy access to everything the Magnificent Mile has to offer, as well as close proximity to the water. The Navy Pier and children’s museum are less than a 10-minute drive from the Gold Coast hotel. The midwest Four Seasons has massive guest rooms with views of Lake Michigan, marble bathrooms and up to 2,700 square feet of space. Four Seasons hotels are family-friendly and offer children’s programs and crafts. The property has a luxe spa, pool and fitness center and provides a vibrant nightlife at its on-site lounge with DJ’s.
Park Hyatt
One of the top luxury hotels in downtown Chicago is the skyscraping Park Hyatt. The large guest rooms have a calming atmosphere with exquisite amenities like soaking tubs, rain showers, kitchenettes and walk-in closets. You’ll enjoy scenic views of Lake Michigan or the Water Tower, and some rooms even have in-room fitness equipment. Once you’ve worked up an appetite, visit the on-site NoMI Kitchen restaurant for views through floor-to-ceiling windows and American dishes with French inspiration. The Park Hyatt Chicago is a pet-friendly hotel with a 24-hour fitness center, on-site florist, free WiFi, room service and a pool.
Viceroy Chicago
This Gold Coast hotel in downtown Chicago has a long list of luxurious amenities. Use the hotel’s Tesla vehicles, enjoy views of Lake Michigan from the rooftop bar, relax in the outdoor pool surrounded by city views or visit the fitness center. The Viceroy Chicago has an on-site restaurant as well as room service. Guest rooms have floor-to-ceiling windows to showcase the city’s skyscraper and water views. The artistic and eye-catching decor plays with a variety of textures and colors, including accents of gold and mid-century modern elegance.
The Ritz-Carlton Chicago
Located right by the Museum of Contemporary Art and prime shopping at the Magnificent Mile is the Ritz-Carlton Chicago. The hotel’s luxe decor is incredibly artistic and elegant, and the guest rooms are packed with opulent amenities and finishes. You’ll love the glass-enclosed separate tub and rain shower and views of the Navy Pier, Lake Michigan and skyscrapers. The Gold Coast Ritz features a fitness center, spa and indoor pool. There is a light and airy on-site restaurant that brings the outdoors inside with floor-to-ceiling windows and foliage. The hotel’s Italian steakhouse has a stylish bar and rooftop lounge.
The Peninsula Chicago
This Windy City version of the 5-star hotel chain boasts a Forbes Five Star rating and five diamonds from AAA. The Peninsula Chicago stands out with its wide range of guest rooms and suites that offer from 531 to 3,645 square feet of space and views of Lake Michigan and Michigan Avenue. If you love Chinese cuisine, you will especially enjoy the on-site Shanghai Terrace restaurant, which has been voted the best Chinese restaurant in the city. The Peninsula Chicago has specially curated dishes for plant-based diets. The hotel also offers a modern American restaurant, bar and lounge on a terrace, and room service. Other amenities include an indoor pool, hot tub, spa and fitness center.
The Langham Chicago
When you stay at the Langham Chicago, Millennium Park, the Navy Pier and Gold Coast beaches on Lake Michigan are just minutes away. The large guest rooms have picturesque city views through floor-to-ceiling windows opening up to the skyscrapers, Chicago River and Lake Michigan. Rooms are elegantly decorated with chandeliers, pianos and spacious seating areas, and some suites come with access to a private lounge. If you prefer not to opt for room service, The Langham Chicago has two American restaurants and serves afternoon tea. Guests appreciate the relaxing on-site spa, indoor pool and fitness center.
