A Chicago Historic Hotels guide
Ten landmark stays our editors return to — chosen for architecture, comfort, location, and a great story.
Chicago has more grand historic hotels than almost any American city — the legacy of a turn-of-the-century building boom and the architects who invented the skyscraper here. These ten are the ones we’d book first. Every one is a working landmark you can actually stay in tonight.
Henry Ives Cobb’s 1893 Venetian Gothic clubhouse on Michigan Avenue is now one of Chicago’s most beloved hotels, with a buzzing game room, the Cindy’s rooftop overlooking Millennium Park, and interiors that still feel like a gilded private club.
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Set in William Le Baron Jenney’s 1894 New York Life Insurance Building, the Gray pairs a dramatic marble-clad lobby with polished service — a top-rated stay in the heart of the LaSalle Street financial district.
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Chicago’s grande dame since 1920, the Drake anchors the north end of the Magnificent Mile with afternoon tea in the Palm Court and old-world glamour overlooking Lake Michigan.
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Behind a dark-green-and-gold terra-cotta facade, the Burnham Brothers’ 1929 Carbide & Carbon Building is one of the city’s great Art Deco landmarks — reborn as the sleek, design-forward Pendry.
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Perched where the river meets Michigan Avenue, Alfred Alschuler’s 1923 London Guarantee Building offers one of Chicago’s best rooftop bars and front-row views of the Wrigley Building and DuSable Bridge.
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“The Hotel of Presidents” has hosted a dozen of them since 1910, and it’s where the original “smoke-filled room” entered American politics — a Beaux-Arts landmark on South Michigan Avenue.
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America’s longest continuously operating hotel traces its roots to 1871; the current Holabird & Roche building dazzles with a frescoed lobby ceiling — and claims the brownie as its own invention.
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The 1895 Reliance Building is a glassy proto-skyscraper that pointed the way to the modern high-rise; today Staypineapple fills this National Historic Landmark with bright, playful rooms.
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Opened in 1927 as the Stevens — once the largest hotel in the world — this Grant Park landmark still impresses with its grand ballrooms and a sweeping lakefront setting.
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A 1924 Michigan Avenue landmark, the Allerton’s rooftop “Tip-Top-Tap” was a Jazz Age icon; the Italian-Renaissance tower remains a warm, well-located Mag Mile stay.
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