Staypineapple Chicago
1 W. Washington St.
In a city known for world-ranking skyscrapers, the 14-story Reliance Building seems downright shrimpy, but more than a century ago it boasted a state-of-the-art design. Its large plate-glass windows predicted the soaring glass-and-steel towers of today, although its signature white terra cotta cladding betrays its 19th-century origins. Having fallen into disrepair in the mid-1900s, the Reliance Building has been restored and now houses a AAA Three Diamond® boutique hotel: Staypineapple Chicago. Guests here can step from the elegant lobby right into the heart of the action in Chicago’s Loop.
The Drake, A Hilton Hotel
140 E. Walton Pl.
Opening its doors in time to greet the prosperous Roaring ’20s, The Drake reigns supreme among Chicago’s grand historic hotels. All but guaranteed to be a landmark from day one thanks to its prime location overlooking Lake Michigan and Oak Street Beach, this AAA Four Diamond hotel looms large on the Magnificent Mile, its rooftop sign visible from afar. Inside the Italian Renaissance-style building, crystal chandeliers, showy flower arrangements and sumptuous ballrooms transport guests to an era of early 20th-century opulence.
Hampton Inn Chicago Downtown/N Loop/Michigan Ave
68 E. Wacker Pl.
We may be biased, but this AAA Three Diamond hotel clearly belongs on this list and not just because it was originally built as the Chicago Motor Club’s headquarters. This narrow Art Deco treasure was built in 1928 with a classic streamlined design, stylized ornamentation outside and a large, colorful mural showing a U.S. road map inside the gleaming, three-story lobby. Offering an added reminder of this downtown Chicago hotel’s origins: A 1928 Ford Model A prominently parked on a second-floor balcony overlooking the lobby’s polished terrazzo floors.
The Langham, Chicago
330 N. Wabash Ave.
You won’t find a better example of the minimalist International Style than this black, aluminum-and-glass box designed by Mies van der Rohe. Known as IBM Plaza when it was completed in 1973, this Chicago landmark may have an austere, uninviting exterior, but don’t be fooled—a recent renovation transformed 13 floors into one of the poshest hotels in town: The Langham, Chicago, a AAA Five Diamond hotel. Within walking distance of the Loop and Magnificent Mile shopping, The Langham occupies a high-profile site next to another architectural icon: the quirky, corncob-shaped Marina City towers.
Palmer House - A Hilton Hotel
17 E. Monroe St.
The Palmer House has been welcoming visitors to Chicago since 1873 although the current Classical Revival-style building dates back “only” to 1925. This massive AAA Four Diamond hotel has more than 1,600 well-appointed rooms, but it’s the gorgeous lobby that guests won’t forget. With a domed ceiling adorned with paintings and gold-leaf trim, the opulent space looks more like a reception hall in a European palace than a hotel lobby. Visitors also love The Palmer House’s downtown Loop location just a couple blocks from the AAA GEM® The Art Institute of Chicago.
The Peninsula Chicago
108 E. Superior St.
This AAA Five Diamond luxury hotel knows how to pamper guests. Top-notch service and a praise-worthy spa combined with the contemporary elegance of its Asian-influenced décor create a setting both lavish and comfortable. The Peninsula embraces the latest technology allowing guests to control their room’s climate, sound system and TV with tablets. But for architecture lovers, the hotel’s main appeal will no doubt be its Magnificent Mile location with fantastic city views that include such iconic structures as the Historic Water Tower and John Hancock Center.
Radisson Blu Aqua Hotel
221 N. Columbus Dr.
A modern masterpiece only recently added to the city skyline, the Aqua Tower manages to stand out among Chicago’s forest of skyscrapers thanks to its unique wavy profile that you might mistake for an abstract sculpture if it wasn’t for its size. Contoured balconies of subtly varying dimensions create the effect of a vertical terrain of hills and ponds. The AAA Four Diamond Radisson Blu Aqua Hotel occupies 18 floors and the ultramodern design continues inside with sleek, stylish furnishings and décor.
Silversmith Hotel Chicago Downtown
10 S. Wabash Ave
Completed in 1897, the Silversmith Hotel was designed by the prestigious Chicago firm behind New York’s Flatiron Building and Washington D.C.’s Union Station. Unfortunately the raised tracks of the “L” on Wabash Avenue obscure Silversmith’s lovely old façade—a blend of Romanesque Revival and Arts and Crafts styles. Inside this AAA Four Diamond boutique hotel, the décor is stylish and unmistakably 21st century, from the marble-accented lobby to the plush, modern guestroom furniture. This downtown hotel takes its name from its previous role as studios for silver craftsmen in the Jewelers Row District.