There’s something irresistibly nostalgic about Chicago’s architecture. Its iconic high-rises—from the Wrigley Building to the neo-Gothic Tribune Tower—evoke the city’s roaring 1920s heyday, when jazz spilled from basement clubs and Prohibition was in full swing. A century later, these landmarks still stand tall, timeless symbols of American design at its most elegant. I felt that history came alive the moment I stepped through the Art Deco façade of The Robey.
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BOOK WITH US FOR PERKS
- VIP status
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- Daily breakfast for two
- Special amenity or local experience worth min $50 per stay on guestrooms and $100 per stay on suites
- Room upgrade subject to availability
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Towering 203 feet above the intersection of Damen, Milwaukee, and North Avenues in Wicker Park, this former office building was occupied by Perkins, Chatten & Hammond in 1929. Belgian design duo Nicolas Schuybroek Architects and Marc Merckx Interiors honored its past while transforming it into a sleek, 89-key boutique stay.
At check-in, I noticed the eponymous Art Deco color palette: emerald green paint on the authentic key cabinet behind the front desk, black-and-white marble-clad walls, and maroon leather upholstery that popped against a backdrop of neutral grays and browns. Original touches—like the 19th-century gold elevators and an old U.S. mail chute—further underscore the building’s historic aura.
The guest room corridors nod to the building’s former corporate life, where framed floor plans hang like archival blueprints of a bygone era. The Tower Rooms—housed in the triangular Northwest Tower from floors three to twelve—are awash in natural light that spills across polished hardwood floors. Details like custom terrazzo tiling, Calacatta marble tabletops, and bold oxide-red accents bring a refined, modern edge that’s equal parts function and flair.
Over in the reimagined Annex Lofts on levels three and four, the building’s industrial bones are proudly on display: raw cement ceilings, exposed concrete walls, and factory-style windows lend an authentic, lived-in charm. Multi-bedroom layouts are thoughtfully appointed with bespoke Delordinaire bunk beds and Schoolhouse Electric sconces, striking a balance between utility and warmth. It’s a nod to the building’s 9-to-5 past—only here, the work-from-anywhere ethos feels more like a lifestyle than a grind.
When it comes to food and drink, you could easily spend the whole day at the hotel. Café Robey, helmed by Chef Michael Elliott, is an all-day diner with serious retro charm—the kind of place Ferris Bueller might’ve hit on his day off. Stop by around 2 p.m. for duck hash, biscuits and gravy, or house-made sausage patties with mustard. Here, breakfast knows no bounds.
After a leisurely late lunch at Café Robey, ease into the evening with cocktails upstairs at Clever Coyote, a ‘90s-inspired hideaway where tiki drinks meet nostalgic bar bites—buffalo wings, fried pickles, and frozen peanut butter pie, to name a few. The retro energy is dialed all the way up with a Street Fighter arcade game, shuffleboard, billiards, and a soundtrack straight out of an old mixtape.
As night falls, take the elevator to The Up Room, the hotel’s sleek 13th-floor rooftop lounge. With panoramic city views and a sultry skyline glow, it’s the perfect nightcap perch. Order a Robey Old Fashioned or a crisp Sauvignon Blanc, and graze on charcuterie, marinated olives, and spiced nuts as the city buzzes below.
When it comes to a Windy City stay that captures the energy, style, and soul of what many call the “pulse of America,” The Robey more than delivers.
Top Takeaways
Location: Wicker Park, Chicago
Rating: 5-Star
The vibe: An Art Deco homage in Chicago’s hip Wicker Park, complete with a hang-worthy café, a second-floor game room, and a rooftop bar boasting sweeping skyline views.
Our favorite thing about the hotel: The 13th-floor rooftop lounge, The Up Room. Come for the summer nightcaps, stay for the twinkling skyline and sultry vibes. It’s easily one of the sexiest spots to meet in the city.
Food + Drink: Café Robey is your anytime breakfast haven, where Chef Michael Elliott’s seasonal spins—like spring’s carrot cake and coconut buttermilk pancakes—strike just the right sweet-savory chord. Upstairs, Clever Coyote channels retro dive-bar charm with cheeky cocktails, arcade games, and late-night bites. For a dressier affair, head to The Up Room, the rooftop lounge where city lights, chilled wine, and a seriously stylish crowd set the summer scene.
Amenities: Rooftop pool; Le Labo toiletries; Complimentary bikes; Room service; Bar; 24 hour front desk; Free WiFi
What’s nearby? Wicker Park; Oz Park; Lincoln Park; Chicago History Museum; Chicago Riverwalk; Chicago Lakefront Trail
Any personal neighborhood recs? Start your stroll at Reckless Records, where flipping through vinyl feels like a local rite of passage. For dinner, snag a seat at Daisies—their handmade pastas are just as chic as the crowd—then slip into The Violet Hour for moody lighting, serious cocktails, and the kind of date-night energy that makes you want to linger.
Rooms: 89
Pricing: Rates start at $170 per night.
Closest Airport: Chicago O'Hare International Airport or Midway International Airport
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