The St. Regis Chicago — Hotel in Chicago

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.||||---||||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.||||---||||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.||||---||||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.||||---||||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.||||---||||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.||||---||||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...

I have to say, I wasn't too impressed.

A disclaimer though, I booked the hotel on points when I found a deal. I was here for only one night and redeemed a very cheap rate.

​​The physical design of the hotel is very beautiful. It helps that dark blue is my favorite color but I enjoyed the look of the rooms a lot. The bed was very comfortable, the room was well equipped, the shower comfortable, etc.

The service however just felt a little less polished than I'd expect. Admittedly I've only stayed in one other St Regis, in Osaka, but I guess I expected a bit more.

At checkin, my room wasn't ready so they offered to store my bags. No big deal; I was there around 2 o'clock. The person checking me in certainly wasn't rude, but he rattled off a comically long list of which amenities were available and what times they were in such a monotonous manner that I got scared I should be taking notes. But okay, maybe he was new and a bit nervous about getting it wrong. I thank him, turn to leave, and then he calls out to me asking if I have any guests. I turn back, say no, and then he proceeds to tell me that if I have any guests coming over, he can upgrade me to a bigger room for $100. I am Titanium Elite. Of course not all open inventory is available for free upgrades with Bonvoy, but to be stopped on my way out of the building to have a hotel actively try to sell me an upgrade that a casual reading of my benefits might ostensibly imply should be free left an awkward taste in my mouth. And to use a legitimate question about number of guests as a segue into the pitch gave off used car salesman vibes in the worst possible way.

The room was beautiful but had terrible noise isolation. I could hear every car going by outside all night. There was an unvacuumed crumb on the ground by the bed. And the bulk shampoo dispenser was almost out. It was doing the thing where it would sputter and barely put out a single drop with each pump.

In Osaka, after I checked in, my butler proactively came to my room to introduce themselves, show me around the room, and offer me a welcome beverage. There was also a snack of some cookies on a plate in the room already. Here, none of that happened. No gift in the room, no butler came to introduce themselves. Not that I needed the help unpacking for a one night stay, but I thought the human touch in Osaka was nice. The lack of welcome gift in the room was a more glaring omission. ​​​​​​ The breakfast credit was $60 at the restaurant upstairs. I got the Japanese breakfast and some juice which after tip came out to exactly $60. There's a 3% service surcharge that the menu says you can ask to have removed. I tried it and yeah, they totally will if you ask.

The restaurant first sat me down next to a wall with half a dozen flies and mosquitoes buzzing around it. When I pointed it out to my waiter, he kindly moved me closer to the middle of the restaurant. That was appreciated, but maybe a five star hotel restaurant shouldn't have a corner of the room infested with flies?

Oh and the fire alarm went off at 5am. After everyone evacuated outside, the front desk waved us all right back in with an unceremonious "sorry, false alarm."

The stay did end on a positive note, luckily. I requested 4pm late checkout and it was honored fully, with my keycard working until 4 and no one knocking to bother me until I left on time. Also the lady working the front desk when I checked out was extremely friendly. Frankly that was the type of service attitude I expected across the stay; having it be the last interaction I had with the hotel definitely left me feeling better about the experience than I otherwise would've. ​​​​​ So, in conclusion, this was by far the best hotel I've ever redeemed so few points for, but that is not the bar a luxury hotel needs to clear. Looking at the $1000+ cash rates they're trying to charge people, for the experience I had, I honestly don't think the standard of service is quite up to the five star level I'd have expected from...

Really nasty staff here. My spouse arrived about an hour before me due to terrible traffic on the Kennedy. I used the Bonvoy app to DM a request to let him check in as we have done dozens of times before in my 1375 lifetime nights at Marriott, where I’ve never had a problem like this or met someone as nasty as the front desk manager. To login to the Bonvoy app requires a password & MFA. I was in an Uber and tried to call the Titanium Bonvoy line but had a bad signal & couldn't get through. But it should be noted the Bonvoy app is more secure than calling in. We were later told that extra scrutiny is applied to someone else checking in with a different last name. When I explained that letting a female with the same last name check in for their husbands reservation, but not my spouse felt homophobic the manager went off on me and told me they were cancelling my reservation, even though I never confirmed that as my intention.

Two things at play here. If they cancel your reservation, you can’t leave a survey with Marriott. They also don’t want people using points or certificates to stay, so they’ll do little things to make it difficult for them. The front desk manager had the gall to tell my spouse that I cancelled the reservation even though I have Bonvoy DM’s showing that he/she said they were canceling it. I talked to the Bonvoy Titanium line who apologized for the hotel's behavior and also indicated that the hotel told them to cancel the reservation. So not only nasty, but dishonest, what a classy property. They kept saying I cancelled it even though I only asked if it was cancellable. They’re the ones who demanded that it be cancelled.

We stayed at the Swissotel down the street instead who upon hearing of our travails and St Regis experience, gave us a beautiful suite for my spouses birthday.

I will be filing Small Claims next week for all of our hotel and breakfast expenses. St Regis knows who I am and has a chance to fix it before I file, but I’d almost rather they didn’t because they need to learn a lesson. Just because I said a policy felt homophobic doesn’t mean you get the right to be offended and cancel my reservation. Tell me why you disagree and show me how we can resolve it. Instead we got lies about who was cancelling the reservation and mass confusion.

If you’re a member of the LGBTQ+ community, this is not the place to stay. We’re second class.

ETA: My spouse was accused of having bought or bartered for my points, because of different last names, at check-in. Marriott policy doesn't even prohibit gifting, but that was not the case. As residents of a community property state, my points and my reservations are legally my spouse's jointly. We were asking for him to be able to access something legally his. More importantly, I'm sure this hotel will talk about how they go the "extra mile". I was going to be there within 45 minutes. It's not even a half a step to say "welcome, we are happy to let you use the room but we do need the primary guest to be here within the hour to continue the stay." Like how hard would that have been? Undoubtedly they did more or other guests that evening, but alas they went a nasty route instead of a...