The Top 34 Hotels Near Easy Does It
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Grupo Habita resurrects a 1929 Art Deco tower in Wicker Park, transforming office floors into 89 rooms and a restrained sequence of cafés that feel less like hotel amenities than deliberate spatial interventions. A Belgian design team's hand is evident in every corner, most strikingly in the 13th-floor bar, where indoor and outdoor dissolve into each other.
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A Hong Kong luxury hotel sits unlikely on the Magnificent Mile, trading the expected Chicago sobriety for lacquered surfaces and imperial ambition. Whether such polish translates to the heartland remains the question that animates every gilded corner.
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The Langham occupies Mies van der Rohe's final Chicago tower, a modernist monument on Wabash where glass and steel meet contemporary luxury. Its restrained elegance—crisp service, refined interiors, meticulous attention—reflects the building's uncompromising architecture rather than chasing spectacle.
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The Waldorf Astoria Chicago announces itself through a soaring English courtyard and marble lobby that recall Art Deco grandeur without the pretension. Service moves with balletic precision throughout the property, and staff decline gratuities as a matter of principle—a gesture that feels less like restriction than Midwestern hospitality.
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A 92-story tower of glass and concrete anchors itself to the Chicago skyline with the kind of architectural confidence that seems almost inevitable in retrospect. Inside, clubby woods and floor-to-ceiling views compose a studied luxury, while Terrace 16 serves modern American cooking against the city's iconic profile.
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A glass tower that bows and sways above the Gold Coast, anchored by a meticulously reconstructed 1920s façade that refuses to disappear into the lobby behind it. The Viceroy trades in that peculiar luxury of having it both ways—gloss and restraint, new money and old bone.
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This lakefront tower on the Magnificent Mile offers understated luxury and an indoor pool that feels like an oasis above the city's retail heart. The restaurant and bars welcome locals and guests alike, anchoring a hotel where crisp design and proximity to Chicago's finest shops create a seamless urban refuge.
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The Gwen wraps itself in salvaged Art Deco grandeur—its façade lifted from a 1929 building, its name borrowed from sculptor Gwen Lux—while housing a contemporary luxury hotel behind those gleaming bones. A rooftop bar with firepits and weekend tea service in the lounge make it less a place to sleep than a portal to a more ornate Chicago, one that still smells of money and old stone.
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A glossy modernist tower on the Magnificent Mile that has aged into its role as anchor tenant of Chicago's hotel landscape, with the Museum of Contemporary Art across the street and Lake Michigan framed in floor-to-ceiling glass. The art-forward interiors suggest a place that knows its geography and has spent decades learning how to exploit it.
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A boutique hotel where sharp modernist design meets genuine warmth, Thompson Chicago trades exclusivity for the kind of hospitality that makes strangers feel like regulars. Its public spaces—all light and confident angles—function as a magnet for both travelers and locals seeking a cocktail or meal in a room that somehow manages to feel both polished and inviting.
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The 1929 Carbide & Carbon Building, all dark stone and gold leaf, houses Pendry Chicago with the grandeur its Art Deco skeleton demands. A contemporary luxury hotel that treats the Loop's architectural drama as both backdrop and design principle, it succeeds by knowing when not to compete.
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Perched where the Chicago River meets the lake, the St. Regis commands classic skyline views from rooms of unhurried luxury and ample proportion. The service—attentive without hovering—justifies the stay more than the spa or either restaurant ever could.
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Across from Wrigley Field, this boutique hotel channels its namesake architect through leather wingbacks and mid-century furnishings set against dark wood and copper. The rooms overlook the ballpark, and nine restaurants downstairs ensure you need not leave before first pitch.
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The hotel rises within Water Tower Place on the Magnificent Mile, steps from the Art Institute and the historic water tower that survived the Great Chicago Fire. Luxury here means proximity—to Chanel and Cartier on one side, to Navy Pier and the lake on the other.
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A former publishing house turned bed-and-breakfast, this eleven-room refuge on May Street honors Chicago authors with literary-minded decor and salvaged architectural details—a double-sided fireplace anchors the common area like a declaration of intent. Each suite offers clawfoot tubs and curated art collections that feel less like hotel dressing than the accumulated taste of someone who reads.
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A 52-floor tower in Streeterville that courts both business travelers and leisure visitors with architectural polish and Chicago swagger. The rooftop lounge, chef-driven restaurant, and 75-foot pool suggest a hotel confident enough to treat its lobbies and corridors as destinations unto themselves.
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The Guesthouse Hotel outfits its spacious suites with full kitchens and private balconies overlooking Andersonville's quiet streets, a setup that dissolves the boundary between hotel and home. A rooftop deck and library—where afternoon tea arrives from a neighborhood patisserie—anchor the kind of lingering stay the place seems designed for.
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A former meatpacking warehouse in Fulton Market, transformed into a sleek boutique hotel where industrial bones and contemporary design coexist without apology. The Hoxton's transatlantic sensibility—born in East London, now rooted in Chicago's post-industrial landscape—suggests a concept that understands its own portability.
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A Venetian Gothic fortress from 1893 reopens as a boutique hotel where gilt cornices and period plasterwork meet contemporary furnishings in studied equilibrium. The Chicago Athletic Association traffics in the particular luxury of making old rooms feel new again without erasing what made them matter.
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In a converted 1908 warehouse on the cusp of Fulton Market, Soho House Chicago operates as something between a members' club and a destination unto itself, drawing on decades of precedent in London and New York. The industrial bones of the building remain visible, a reminder that comfort here arrives not through erasure of the past but through its careful curation.
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The Talbott holds its 1920s bones lightly on Chicago's Gold Coast, a vintage hotel lobby that hasn't been cosmeticized into theme-park pastiche. Kara Mann's recent renovation threads contemporary ease through art-deco bones, letting old architecture breathe.
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River North's energy pulses through this hotel where the lobby bar pivots from daytime workspace to evening drinking den, fueled by local spirits and Friday night DJ sets. The shuffleboard tables and taco counter suggest a place more interested in collision than comfort, and it works.
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The Sofitel Chicago Magnificent Mile rises as a stark white wedge on the Magnificent Mile, its geometric form the work of architect Jean-Paul Viguier uncompromised by adaptive reuse. Built from nothing rather than retrofitted into the past, the hotel embodies a deliberate modern vision—clean, sculptural, unapologetic.
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The hotel rises into Chicago's skyline with the confidence of a city that perfected the skyscraper, all clean lines and modernist faith in vertical space. Rooms capture that same optimism—contemporary luxury filtered through midcentury restraint—making the Magnificent Mile address feel less like tourism and more like inhabiting the city's architectural dream.
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The Acme Hotel Chicago occupies the rare slot in this city's boutique landscape where work recedes and a younger, looser energy takes hold. Its stripped-down rock-and-roll sensibility stands apart from the polished business hotels that dominate the scene.
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A tower on the Chicago River that marries scale with intimacy, offering sky-high pools and full business facilities without surrendering the warmth of a smaller place. The Royal Sonesta proves that size need not calcify hospitality—pets roam freely, children are tended to, and Midwestern generosity persists even in the lobbies of high-rises.
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A boutique hotel that wears Chicago's art-historical lineage across its lobby and halls, from Depression-era social realism through the Imagists' playful abstractions. The rooms themselves are spare and modern, letting the city's creative restlessness do the talking.
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A luxury boutique hotel on the Miracle Mile that fuses art and science through books, inventive design, and Art Deco touches—its name references Einstein for reason. The rooms prove that intellectual rigor and elegant restraint belong in the same conversation.
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Perched above the Chicago River's bend where it meets the Magnificent Mile, this luxury hotel commands views of the Riverwalk's constant motion and the Art Deco Tribune Tower beyond. The rooms and suites face outward onto a landscape of water and historic architecture that few downtown properties can claim.
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A century-old insurance headquarters on West Monroe has been revived as the Gray, where soaring ceilings and period bones meet the spare geometries of mid-century modernism. The result feels less like a hotel than a living argument for why Chicago's architectural DNA still matters.
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A swanky modern hotel housed in a landmark Art Deco tower once occupied by Chicago's two largest banks, the LaSalle channels retro glamour through its rooms and lobby lounge where the city's dealmakers gather. Grill on 21 operates as a classic American steakhouse centered on an open kitchen, all brass and sightlines.
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Arlo Chicago inhabits a 1916 banking landmark steps from Millennium Park, its contemporary rooms framing the city's skyline while a fitness center anchors the ground floor. About Last Knife, the in-house bistro, threads West African and Latin American seasonings through familiar American fare with quiet assurance.
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