25 Chicago Hotels Inside Landmark Buildings
The hotel where ‘smoke-filled room’ was coined, a 1927 giant that was once the largest in the world, an 1895 forerunner of the glass skyscraper, and a Mies van der Rohe tower on the river.
Chicago put its old banks, its athletic clubs, and its early skyscrapers to work as hotels. This list has the Loop tower where ‘smoke-filled room’ was coined, the 1927 giant on Michigan Avenue that was once the largest hotel in the world, the 1895 Reliance Building that pointed the way to the glass skyscraper, and the Mies van der Rohe tower on the river.
The list is grouped by character, not ranked. Where a hotel’s own site could be confirmed, its name links there; the rest are listed without one.
The grand old names
Palmer House, A Hilton Hotel · The Loop
The first Palmer House opened in September 1871 and burned in the Great Chicago Fire thirteen days later; it was rebuilt and reopened in 1875 as an early fireproof hotel. The merchant Potter Palmer built it as a gift for his wife, Bertha Honoré Palmer. The present building, the third Palmer House, opened in 1925 to designs by Holabird & Roche. The Palmer House brownie is said to have been created in its kitchen for the 1893 World’s Columbian Exposition.
The Drake · Gold Coast
The Drake opened in 1920, designed by Benjamin Marshall of Marshall & Fox. It has put up royalty and heads of state, among them Queen Elizabeth II in 1959. It held the Cape Cod Room seafood restaurant from 1933 to 2016 and keeps the Palm Court tearoom.
The Blackstone, Autograph Collection · South Michigan Avenue
The Blackstone opened in 1910, a Beaux-Arts building by Marshall & Fox. The phrase ‘smoke-filled room’ was coined here after Republican leaders settled on Warren G. Harding as their 1920 presidential nominee in one of its suites. It has housed a long line of U.S. presidents.
Congress Plaza Hotel · South Michigan Avenue
The Congress Plaza was begun in 1893 as the Auditorium Annex, to lodge visitors to the World’s Columbian Exposition. An underground marble passage, Peacock Alley, linked it to Sullivan and Adler’s Auditorium Building across the street. A hotel workers’ strike that began here in 2003 ran for about a decade, among the longest in U.S. history.
Hilton Chicago · South Michigan Avenue
The Hilton Chicago opened in 1927 as the Stevens Hotel, then the largest hotel in the world with about 3,000 rooms. The Stevens family built it; their son John Paul Stevens became a U.S. Supreme Court justice. The Army took it over during the Second World War, and it later ran as the Conrad Hilton.
Former banks
Virgin Hotels Chicago · The Loop
Virgin’s first hotel anywhere opened in 2015, in the Old Dearborn Bank Building, a 1928 Loop high-rise.
Hotel Julian · The Loop
Hotel Julian is in the former Atlantic Bank Building on Michigan Avenue, facing Millennium Park. It opened in late 2018 after an adaptive-reuse conversion by Oxford Capital Group.
JW Marriott Chicago · The Loop (LaSalle Street)
The JW Marriott is in a classical bank-and-office building finished in 1914 by Daniel Burnham’s firm. It opened in 2010, the first JW Marriott in Chicago.
The LaSalle Chicago, Autograph Collection · The Loop (LaSalle Street)
The LaSalle is in the upper floors of the 208 South LaSalle Street Building, finished in 1914 for the Continental and Commercial National Bank. The full-block structure was among the last designs from Burnham’s firm, completed by Graham, Burnham & Co. after his death. It opened as a hotel in 2022.
Kimpton Gray Hotel · The Loop (LaSalle Street)
The Kimpton Gray is in the New York Life Insurance Building, a landmark high-rise in the LaSalle Street financial district dating to the 1890s. It is named for the building’s Georgia gray marble.
Michigan Avenue landmarks
Chicago Athletic Association Hotel · Michigan Avenue
The building went up in 1893 as the clubhouse of the Chicago Athletic Association, a Venetian Gothic design by Henry Ives Cobb facing Michigan Avenue. It was a private men’s athletic club for more than a century before closing in 2007, and reopened as a hotel in 2015.
InterContinental Chicago Magnificent Mile · Magnificent Mile
The hotel went up in 1929 as the Medinah Athletic Club, a Shriners’ club designed by Walter W. Ahlschlager. Its 14th-floor junior-Olympic pool is named for the Tarzan actor and Olympic swimmer Johnny Weissmuller, who is said to have trained there. The tower’s ornament draws on Assyrian, Egyptian, and Moorish motifs.
The Gwen, a Luxury Collection Hotel · Magnificent Mile
The Gwen is in the McGraw-Hill Building, a 1929 Art Deco tower on North Michigan Avenue. It is named for the sculptor Gwen Lux, whose Art Deco relief panels decorate the limestone facade.
Pendry Chicago · Michigan Avenue
The Pendry is in the Carbide & Carbon Building, a 1929 Art Deco tower by the Burnham Brothers, sons of Daniel Burnham. The dark-green terra-cotta tower is capped with gold leaf, often said to evoke a champagne bottle. It was the Hard Rock Hotel and then St. Jane Chicago before reopening as the Pendry in 2021.
Warwick Allerton · Magnificent Mile
The Allerton opened in 1924 as a ‘club hotel’ of small rooms for young professionals new to the city. Its rooftop Tip Top Tap bar was a popular nightspot and radio broadcast site in the 1940s and 1950s.
Towers of the Loop
Staypineapple, An Iconic Hotel, The Loop · The Loop
The hotel is in the Reliance Building, an early steel-frame skyscraper finished in 1895 and a forerunner of the glass-walled tower, designed by Burnham’s firm under John Root and then Charles Atwood. It is a National Historic Landmark, earlier home to the Hotel Burnham, which opened in 1999, and later The Alise. Al Capone’s dentist is said to have kept an office in the building.
The Silversmith Hotel · The Loop (Jewelers Row)
The Silversmith is in the Silversmith Building, finished in 1897 for the city’s silver and jewelry trades, designed by Peter J. Weber of D.H. Burnham & Co. It stands on the old Jewelers Row along Wabash Avenue, a Chicago School building on the National Register.
LondonHouse Chicago · The Loop (Riverfront)
LondonHouse is in the London Guarantee Building, a 1923 Beaux-Arts tower by Alfred Alschuler, on part of the site of Fort Dearborn, the early-1800s Army fort at the mouth of the Chicago River. It opened as LondonHouse, Curio Collection by Hilton, in 2016, taking its name from the London House jazz club once at the corner.
The Langham, Chicago · Near North (Riverfront)
The Langham is in the former IBM Building, now AMA Plaza, at 330 North Wabash, the last American high-rise Mies van der Rohe designed, finished in 1971. It opened on the tower’s lower floors in 2013.
The Midland Hotel, Chicago · The Loop
The Midland is in a historic Loop building that ran for decades as the Midland Hotel. It spent years as W Chicago – City Center before a renovation brought back the Midland name, reopening in 2024 as a Tribute Portfolio hotel.
Jazz Age hotels and clubs
Allegro Royal Sonesta Hotel Chicago Loop · The Loop (Theater District)
The Allegro is in the former Bismarck Hotel, whose building opened in 1926 beside the Palace Theatre. It opened as the Kimpton Hotel Allegro in 1998 and later became the Allegro Royal Sonesta.
Hampton Inn Chicago Downtown/N Loop/Michigan Ave · The Loop
This Hampton Inn is in the Chicago Motor Club Building, a 1928 Art Deco tower by Holabird & Root. Its lobby keeps a restored 1928 mural map of the U.S. highways and a vintage Ford Model A. It was converted to a hotel in 2015.
Freehand Chicago · River North
The Freehand is in the former Hotel St. Clair, built in 1927. The building is said to have been a speakeasy and a mob-era haunt during Prohibition. It reopened in 2015 as the Freehand, part hostel and part hotel, home to the Broken Shaker bar.
The Ambassador Chicago · Gold Coast
The Ambassador opened in 1926 as the Ambassador East, long the home of the Pump Room restaurant, which opened in 1938. The Pump Room’s ‘Booth One’ was kept for the stars who passed through by train, from Humphrey Bogart to Frank Sinatra. It is now owned by the Chicago Hotel Collection, which has worked to bring back the historic restaurant.
The Robey · Wicker Park
The Robey is in the Northwest Tower, a 1929 Art Deco flatiron that was Wicker Park’s first skyscraper. Grupo Habita converted it to a 69-room hotel, opened in 2016.
Frequently Asked Questions
Are these hotels ranked?
No. The groups sort them by character, and the order within each group carries no meaning.
What made a hotel interesting enough for this list?
A story. Every entry was a bank, an athletic club, an early skyscraper, or a grand old name with a documented past. Comfort alone did not qualify a hotel.
Why are there no prices?
Rates change daily and a priced list goes stale in a month. Where a hotel runs its own site, its name links there, so you see the current rate and book direct.
Which hotel puts me closest to the day trips on this site?
Most day trips from Chicago leave by train from Union Station or Ogilvie, or by road along the lake. The Loop and Michigan Avenue hotels sit closest to the stations.
Do the small hotels book out faster than the grand ones?
Usually. The smaller conversions — Hotel Julian, the Chicago Athletic Association, The Robey — hold fewer rooms than the Michigan Avenue giants and fill first. Book those well ahead.