On an all-too-brief return visit to Chicago, where I once lived, I traveled with my wife and grade-schooler. I wanted to make sure we did it in style — not hunched over stools with grape Nehis and dripping Harold’s quarter-white sandwiches, extra bread, on the South Side, but from a throne overlooking Lake Michigan from the Gold Coast.
I booked an executive suite at the Four Seasons Hotel Chicago through Fine Hotels + Resorts (FHR) using The Business Platinum Card® from American Express. With a promotion, I got a third night free when I booked 2 nights. A recent trip to a Four Seasons in Boston had made me an instant fan of the brand, so I saw it as a good opportunity to make sure that hadn’t been a fluke.
Here’s how it went down in Chi-town.
Booking the Four Seasons Hotel Chicago
I booked our stay at the Four Seasons Hotel Chicago on my Amex Business Platinum card, which would have cost $2,450.01 for 2 nights, or $2,876.13 after taxes and fees.
I used 100,000 points at 1 cent per point to knock off $1,000, leaving my out-of-pocket cost at $1,876.13. It was under half of our valuation of Amex Membership Rewards points at 2.2 cents per point, but redeeming those points meant I could more easily meet the 2-night requirement for the hotel promotion that offered a third night for free.
Since this was a Fine Hotels + Resorts property, I got an $85 daily breakfast credit, a $100 hotel credit, and was able to apply a $300 semiannual hotel credit for prepaid bookings through AmexTravel.com for FHR or The Hotel Collection.
1. It’s in a Great Location
I knew we’d be in a prime location for much of what the city’s known for, especially for a first-timer like our son. We were right around the corner from the Magnificent Mile stretch of Michigan Avenue, with its high-end shopping, blocks from Rush Street restaurants, less than a 10-minute walk from Oak Street Beach, and about 2 blocks from the Water Tower.
On the Chicago L, it took us about an hour to get from Chicago O’Hare International Airport (ORD) to the hotel, with a single transfer. Getting back to O’Hare by Uber took us over 2 hours because of standstill traffic on the Kennedy Expressway.
2. We Had a Gorgeous Suite
The executive suite was perfect for an extended weekend, and the rollaway bed was in the living room when we arrived.
We faced east toward the lake, which meant we had fantastic light and a close-up view of the John Hancock Center (now officially known as 875 N. Michigan Ave.), the Palmolive Building (formerly the Playboy Building), and its Lindbergh Beacon, which was added to the top of the Palmolive Building in 1930 to show pilots the way to Midway Airport (MDW). It shone northward in a single, fixed beam for our stay.
The living room was just big enough for 4 adults and 2 grade-schoolers for an ice cream party, and though we found a white-noise machine and earplugs there in case of lake wind, noise wasn’t an issue at all.
We discovered an unexpected fourth guest, a fat little spider that had made its web on the outside of a window in a Jeff Goldblum-in-Jurassic Park moment.
3. Attentive and Meticulous Service
The Four Seasons brand’s most valuable asset is its staff. In Boston, I found them to be proactively attentive without going overboard into cloying — a fine line that less experienced hotel employees can struggle with.
In Chicago, they kept the same standard. There were timing hiccups, particularly when anything had to be brought into the room. Staff members were apologetic, explaining that the weekend was unusually busy. But considering that the hotel was fully booked and the city abuzz with several notable events (end of the Chicago public school year, University of Chicago graduation, 10th-anniversary Pokémon GO Fest, and a final World Cup tune-up match between the U.S. and German national teams), they always made us feel seen and well cared for.
At check-in, the concierge brought our son a basket of goodies to choose from. He picked out a little white puppy stuffy over Slinky toys. Waiting for us in our room were macarons and other sweets.
Our Boston Four Seasons experience had turned me into a big fan of the Four Seasons app, which I found seamless. I put the Chicago staff through their paces via the app before we arrived. They responded quickly and knowledgeably every time.
Was there anywhere near the hotel where I could buy neon-green Chicago hot-dog relish? They gave me the names of 3 places I could walk to that definitely had it. Did the Peloton bikes require us to pack our specialized cycling shoes? No, their Pelotons had pedal cages.
The only “no” was when I asked if they could make Pokémon towel art. They said they couldn’t, which I understood — this wasn’t a cruise ship, after all — but on our third day, the concierge gave our son a Pikachu bath towel instead. That was going above and beyond to turn a no into a yes.
4. Amenities Included a Familiar Pool
The pool was warm and shallow but large enough for several families, the hot tub was relaxing and well-maintained, and the area was kept pristine. The highlight was the massive skylight that hovered over the pool like a benevolent UFO.
If the pool looks familiar, it’s probably because it was featured in “Home Alone 2: Lost in New York.”
The fitness center was large and well-equipped, and we didn’t use the spa at all.
5. Food Was Solid, Especially Room Service
The Four Seasons Hotel Chicago has a single restaurant, Adorn Bar & Restaurant, on the seventh floor.
The weekday à la carte breakfast was not mind-blowing. I ordered the wagyu hash and found that — I can’t believe I’m complaining — there was too much wagyu (it was also somewhat soupy). The presentation was surprisingly lackluster for my wife’s bacon, eggs, and mushrooms, which had been simply tossed on one side of a too-large plate.
The weekend buffet was spectacular, one of my favorites so far ($49 for adults, $26 for kids 12 and under, and kids under 5 free). There was variety, beautifully presented fruits, a decent bagel spread with salmon and cream cheese, and more. I also appreciated that this Western hotel offered steamed pork buns without it being Chinese New Year or some kind of tacked-on theme.
Thanks to Amex’s FHR and The Hotel Collection and Chase’s The Edit, room service has become a tradition in our family.
In contrast to the plating at Adorn on our first morning, the room service cart was picture-perfect. Most was tasty (though I don’t know why I keep ordering bagels outside of New York City or Montreal) and provided a solid start to our last day in town.
For favorite amenities, the pool was neck and neck with the ice cream cart ($30 per person, which we charged against our $100 FHR hotel credit), which a hotel staff member wheeled to our suite with a mess of fixings for ice cream made fresh daily in the hotel. My wife described the vanilla as merely “OK,” but I found the chocolate to be so rich and complex that I’m still thinking about it days later. I finished my whole bowl and wolfed down what my kid didn’t finish. (Our dad friend did the same with his kid’s, too.)
6. The Shower Was Tricky
I’m starting to think the bathrooms are the weakest part of a Four Seasons experience. The bathroom at this hotel was still miles better than 90% of the hotels I’ve stayed at, but there were a couple of nits to pick.
It always took a couple of minutes for the water pressure to build up enough for a shower, perhaps because we were on the 38th floor in a nearly 40-year-old building.
A quirk that this hotel shared with the One Dalton hotel was the unintuitive shower controls. This one required you to turn the control in one direction for the regular, fixed shower head. No problem. But to switch the water flow to the handheld shower head, we had to twist that same control in the opposite direction, not once or twice, but over 3 full rotations before we got the first trickle out of the wand.
Finally, perhaps related to the water pressure issue, we discovered that the toilet didn’t always flush fully, leaving occasional surprises for the next person.
Final Thoughts
I’ve always been mercenary about hotel brands — I never saw the point of owning a co-branded hotel credit card, since I never had strong feelings about where to stay beyond the best deal, the most interesting history, or the aesthetics. But after Four Seasons stays in Boston and Chicago, I may now be a Four Seasons loyalist, and my wife and son may be, too.
If you need a classic Chicago stay in a well-located hotel with amazing views and incredible service, the Four Seasons Hotel Chicago is a no-brainer. Say hello to the spider for me.