From the outside, the St. Regis Chicago resembles five-star hotels in many global cities: soaring curtain walls of glass, a cantilevered entry flanked by manicured hedges, a doorman in a frock coat murmuring into an earpiece. Everything about the exterior suggests classic urban luxury—it suggests, well, St. Regis.
But step inside, and the gap between the brand and the building hits hard and clear. On arrival, I asked an associate to direct me to the lobby, imagining a grand salon tucked just out of view—up a staircase, perhaps, or behind some improbably large double doors.
Instead, he gestured to where I was already standing.
It turns out the lobby isn’t hidden. It’s just… there, encompassing a wide, high-ceilinged hallway with a modest set of desks recessed into one corner like a late-stage design compromise. The space feels more suited to an artsy boutique hotel than a flagship St. Regis.
This makes more sense (as do the other oddities at this hotel) once you learn the St. Regis flag was only applied after construction had already begun, as I discovered later in my stay.
There’s no champagne welcome. No property guide. No printed list of elite benefits. And the check-in—like much of the hotel—seems to assume that being expensive is enough.
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A Gorgeous Suite with Butler Service (Singular, Not Plural)
As an Ambassador guest, I received a multi-level upgrade to a St. Regis Suite, which was spacious, minimalist, and visually arresting, featuring two full bathrooms, motorized drapes, a walk-in closet, and a soaking tub large enough for the entire Chicago Bears offensive line. Floor-to-ceiling views wrapped around the river and lake, and daylight lit the space with a soft, luxuriant calm.
But if the suite was nearly flawless, execution wasn’t. As with most stateside St. Regis properties, butler service is limited to suites, and they really do mean "butler," as there's typically only one on duty at a time. I waited nearly an hour post-check-in before he arrived. When he did, he unpacked everything carefully and professionally—a brief glimpse of the brand’s former self.
Later, desiring a late-night bath, I discovered that the soaking tub didn’t work properly: water flowed only through the attached showerhead. An engineer arrived, declared the diverter broken, and around 1 am, I was finally left to bathe in peace.
Then, exiting the bathroom and flipping on the bedroom TV, I found it unshakeably fixed to the Marriott channel, playing an endless loop of corporate cheer and aspirational branding. I gave up and went to bed.
Attention to detail is not this hotel’s strength. Cotton swabs I requested were delivered, but left miles away from their rightful place on the bathroom vanity.
Washcloths arrived only after multiple follow-ups—thin, frayed, and casually draped over the coffee table like leftover flyers from the Art Institute. On closer inspection, they turned out to be Preferred Comfort, an institutional brand more commonly seen at Best Westerns and airport-adjacent conference hotels. For the uninformed, the official St. Regis towels are tank-door-thick and feature the hotel's logo on the tag.
It’s a small thing, yes. But also a symptom: of cost-cutting, of eroded standards, of a hotel wearing the St. Regis nameplate but quietly offering something less.
Far less, in fact, when a large brown spider took up residence in the suite one night. I called the front desk to report it. The initial response was “Oh,” which is not, strictly speaking, a hospitality-grade apology. I was told engineering was en route. After 30 minutes, I gave up, illuminated the Do Not Disturb sign, and went to bed. The next morning, with the DND removed, no one came. Only after calling again was the situation addressed, still without acknowledgment, much less contrition.
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Dining, Disjointed—and Occasionally DIY
Room service was inconsistent at best, surreal at worst. One morning’s multi-course breakfast arrived with a single fork, no spoon, and no glass for water. Another day, my cappuccino was delivered in a paper cup—a detail that might pass unnoticed at a Courtyard, but lands differently in a suite furnished with crystal and Carrara marble.
Breakfast juice is frozen. Substitutions are not encouraged, even for dietary needs. Asking for berries instead of bacon? That’ll be $10.
The inconsistency likely stems from the hotel’s decision to outsource its entire food and beverage program to Lettuce Entertain You, a local restaurant group with two on-site outlets: Tre Dita, an Italian steakhouse, and Miru, a Japanese-inspired restaurant. The food at both is competent and occasionally excellent, but service can feel split between fine dining and food court.
Tre Dita is loud, crowded, and oddly theatrical—more Milan fashion week than Milanese trattoria—but the homemade pastas are very good, and the kitchen knows its way around a cut of beef. Miru, upstairs, is even louder. My server was attentive and gracious, but the food runners delivered dishes like they were restocking a buffet: fast, a bit clumsy, and entirely without flourish. Prices at both restaurants align with the hotel’s five-star branding. The polish and pacing, less so.
When I tried to arrange a round of drinks for a friend and his partner—a simple gesture at most hotels—the front desk referred me to the restaurant. The restaurant declined unless I could confirm the exact time of arrival. When I explained I preferred to leave it flexible, I was told that was “impossible,” then swatted away like a martini olive in a wellness cocktail.
And speaking of drinks, don't expect any bar snacks. Not even a ceremonial almond. And while the outdoor patio is beautiful, it’s unmanned. You carry your own drink outside, seat yourself, and, if you linger too long, may feel tempted to bus your own glassware.
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Spa and Fitness: Where Relaxation Is Closely Supervised
The Forbes five-star spa at the St. Regis Chicago offers excellent treatments—thoughtful, professional, and blissfully free of the hard sell. If only the space itself felt as confident.
The locker rooms are so compact that using them at the same time as another guest becomes a polite game of Tetris, one where someone inevitably ends up holding their shoes and waiting. The nail room, meanwhile, was hot enough to suggest the hotel had found a way to integrate hydrothermal therapy into standard grooming services.
In the relaxation lounge, I made the mistake of getting too comfortable beneath one of the generously provided blankets. Within minutes, a manager appeared—stern, sudden, and with the energy of a boarding school headmistress—to announce, loudly, that “sleeping is not permitted.”
Apparently, this is the kind of five-star spa where you’re welcome to unwind—as long as you stay vertical, vigilant, and completely unrelaxed.
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The House Car, One Bright Spot
The house car is a Rivian—modern, distinctive, and a bit less practical than the Escalades or Maybachs typically used at peer properties. But the driver, Oscar, is a gem: gracious, polished, effortlessly warm. He embodied the brand more than anyone else I encountered during the stay.
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Laundry and the Paper Bag Problem
Laundered items were returned not in a box, not on hangers, not even wrapped in tissue—but in a crumpled paper bag, the kind usually reserved for takeout or evidence collection. When I requested pressing, the staff confidently informed me it would need to be sent out and wouldn’t return until after 8 p.m.
This, of course, was false. Every St. Regis handles pressing in-house—and on an express basis, no less. But the associate didn’t believe me. I was gently, but firmly, gaslit into thinking that the brand’s most basic service amenity was somehow imaginary.
It’s one thing to miss a detail. It’s another to actively unlearn your own standards.
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Final Thoughts
The St. Regis Chicago is a triumph of architecture and an underachievement of execution. The rooms are stunning, the views almost smug in their perfection. But beneath the polished surfaces, the hotel operates like it’s cosplaying a global luxury icon—rehearsing the lines of five-star service without learning the blocking. The gestures are all there. The instincts are not.
There’s an ambient sense that hospitality is something guests owe the hotel, not the other way around. The result is a curious inversion of the brand: aloof instead of attentive, stylized instead of seamless. By evening, the porte-cochère turns into a staging area for the Glitterati—full of SUVs, stilettos, and small dogs in large handbags—less butler service, more bottle service. It's all very exclusive, provided you don’t mind carrying your own drink to the patio and being ignored once you get there.
If this hotel is trying to position itself as invitation-only, that’s fine. But before playing gatekeeper, it helps to nail the basics, like hiring a housekeeper who can distinguish a towel from a napkin.
Stay here and you’ll get the suite. You’ll get the view. But you’ll also get clothes returned like an Uber Eats dispatch, silverware rationed like wartime, and a lingering sense that you’ve paid for an experience that’s more raw than the sushi at the signature restaurant.
A beautiful hotel, yes. A St. Regis?
Only if you squint.
N.B.: I discussed these concerns with hotel management, who were gracious, contrite, and seemingly surprised. They mentioned having invested in expensive crystal glassware for in-room dining, then paused, visibly confused as to where it had all gone. They promised to follow up. So perhaps the next guest will get their cappuccino in something that doesn’t crinkle.
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