08 October 2025
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In October 2025, our Inspectors announced their latest picks for the most outstanding hotels in the world — distinguishing more than 2,000 accommodations with between One and Three MICHELIN Keys. In Chicago, four hotels earned One Key and three received Two Keys.
These are the best hotels in Chicago, and more than half make their homes in the kind of historic buildings that give this city its well-earned reputation as one of the most architecturally distinguished country. Fittingly, all are within a block or two of the famous Michigan Avenue, itself the setting for some the best shopping and dining in the city.
Chicago Athletic Association
Chicago’s architectural story began before modernism — this Venetian Gothic landmark, previously a private club for the city’s (male) movers and shakers, dates back to the final decade of the 19th century. But now, after a renovation by architects Hartshorne Plunkard and an interior redesign by hospitality wizards Roman and Williams, the One-Key Chicago Athletic Association is a thoroughly up-to-date boutique hotel in that retro-modern, luxury-boutique sort of way.
Pendry Chicago
Only in Chicago can a hotelier reasonably hope to set up shop in a masterwork like the 1929 Art Deco Carbide & Carbon Building, with its stately dark stone and immaculate gold trim. It’s a perfect fit for the Pendry, the urban luxury-boutique cousin to the Montage resorts; the Two-Key Pendry Chicago combines contemporary boutique-hotel good looks with upscale comforts and impressive views of the distinctive Loop cityscape.
The Langham Chicago
This is a skyscraper hotel, American-style, which means, in contrast with its Asian cousins, that the hotel occupies the bottom floors rather than the top. (The views from twelve floors up, in this town, are scenic enough.) 330 North Wabash, formerly known as IBM Plaza, was the last work of the modernist master architect Ludwig Mies Van der Rohe. Once you’re in your room you’ll find you’ve left Mies’s high modernism behind — though there’s some mid-century influence visible, the look is more obviously influenced by the Langham group’s Hong Kong and London roots. Space is plentiful, as is sunshine, and the details are impressively selected, right down to the well-stocked minibar.
The Gwen
One-Key the Gwen doesn’t just echo the aesthetics of Twenties and Thirties Chicago, it’s an authentic piece of history — its façade comes from the 1929 McGraw-Hill building, and it’s named for the sculptor Gwen Lux, whose work still adorns it today. Inside it’s a thoroughly contemporary boutique-style luxury hotel, with Art Deco accents and 21st-century comforts. There’s a pan-Mediterranean restaurant, an open-air rooftop bar (complete with firepits), and a weekend “Tipsy Tea” served in the hotel’s lounge; an ideal prelude to an afternoon in what might be one of Chicago’s finest shopping districts.
The Peninsula Chicago
In the middle of Chicago’s Magnificent Mile of department stores and designer boutiques is the Two-Key Peninsula Hotel, only the third in America. The Peninsula’s brand of Hong Kong luxury has fared well in New York and LA — and any doubts here are immediately laid to rest by the uniformed bellboys, spiriting guests’ bags to the lobby before the cab driver can lay a hand on them. Other staffers seem possessed of a psychic ability to remember every guest’s name at once, a delightful contrast to the typically American nod-and-smile.
Waldorf Astoria Chicago
One look at the huge English courtyard, or the museum-like marble lobby, and it’s clear that this is a full-scale luxury hotel all the way — especially since all this black, white, and polish gives off a dazzling Art Deco vibe. Fortunately this One-Key hotel undercuts its potentially chilly elegance with outstanding service, for which no staff person is allowed to accept a tip.
Viceroy Chicago
The Viceroy hotels exist at the intersection of luxury-hotel extravagance and boutique-hotel tastefulness, and the One-Key Viceroy Chicago is no different. The building, a gently undulating glass tower, is pure luxe modernity, but the lower floors blend effortlessly into Chicago’s Gold Coast, thanks to the meticulously preserved façade of the 1920s-vintage Cedar Hotel, which was reassembled brick by brick once the tower was complete.Top image: The iconic, historic facade of the Pendry Chicago. ©Pendry Chicago
