Chicago Bounces Back


Value has been hard to come by this year. Since we pay full price for all the hotels we review, we have felt the surge in room rates just like everyone else. Fortunately, there are still some wonderful places in the United States where plush accommodations can be had at a reasonable cost, perhaps even at a discount. Chicago is one of those places. Because big cities haven’t seen the demand spikes experienced by beach resorts and national parks, their hotel prices haven’t increased so steeply. During our summer stays, we discovered room rates that were perhaps 30 percent less than usual, and more important, we had a sensational time visiting uncrowded museums and dining in superlative restaurants. This autumn is an ideal time for a long weekend in the city.

The Peninsula Chicago vs. Four Seasons Chicago

The 25-meter pool at The Peninsula Chicago
The 25-meter pool at The Peninsula Chicago - Photo by Andrew Harper editor

The question Andrew Harper members most commonly ask our travel advisors about Chicago is, “Which is better, the Four Seasons or The Peninsula?” The two properties are a short walk from each other along Michigan Avenue, they have similar prices, and our ratings of them are always close. But the Four Seasons just reopened after a major renovation, and I wondered if that might give it the edge over The Peninsula, currently ranked as the favorite by two points. It was time for an anonymous reevaluation.

As an initial test, I asked the concierges of both hotels to assist with one of Chicago’s most difficult restaurant reservations: Rose Mary. It was no surprise to receive a quick response from The Peninsula, saying that because the restaurant does not answer its phone or emails, they were unable to help. But I was amazed to learn that a Four Seasons concierge had managed to secure a table on one of my requested dates at an ideal time. Advantage Four Seasons.

The Four Seasons just reopened after a major renovation, and I wondered if that might give it the edge over The Peninsula, currently ranked as the favorite by two points. It was time for an anonymous reevaluation.

The arrival experiences at the hotels are quite similar, with quick valets, small street-level entry lounges and main lobbies several floors up. The Four Seasons has greatly improved the look of these spaces. Exiting the elevator, one faces a mini allée of (faux) flowering trees standing on a striking black-and-white marble floor. Hundreds of delicate golden leaves dangling from the ceiling warm the otherwise monochrome hall. To the right are the reception and concierge desks, the former backed by a wall of lustrous metallic cubes. They reflect the natural light that now reaches the front desk, formerly cut off from the windows at the opposite side of the building. Running between the newly brightened reception area and an art deco-style bar is the lengthy lobby-lounge, with seating groups in tones of gunmetal, silver and cream. Unfortunately, the lounge had no food or beverage service at the time of our visit, but that was scheduled to change this month.

To the bar’s right is the new Adorn, a minimalist restaurant helmed by James Beard Award-winning chef Jonathon Sawyer. Most tables were empty when we dined, perhaps because the Four Seasons has historically been better for high tea than dinner. No longer. Our meal was delicious, though the menu was occasionally misleading. The “crispy confit of chicken wings” had many admirable qualities, but crispiness was not one of them. Similarly, I very much enjoyed the light river trout, but the “sauce meunière” turned out to be a beet purée. The bowl of al dente bucatini in a cognac-butter sauce topped with lardons and lobster both deserve unqualified praise.

View from the Z Bar terrace, The Peninsula Chicago - Photo by Andrew Harper editor
Room service to our Grand Premier King Room, The Peninsula - Photo by Andrew Harper editor
Sitting area of our Grand Premier King Room - Photo by Andrew Harper editor
Work desk of our Grand Premier King Room - Photo by Andrew Harper editor
Bath of our Grand Premier King Room - Photo by Andrew Harper editor
Sundeck near the pool - Photo by Andrew Harper editor

The Peninsula’s entrance and lobby have changed little since my last visit, but they remain impressive. Off the elevators, a vitrine-lined hall leads to the concierge desk, framed by a dramatic golden bas-relief of flappers posing in front of Chicago’s skyline. To the left is the sunny reception area, and to the right is the Lobby, a restaurant and lounge with soaring gilded ceilings and a sweep of double-height windows. The Four Seasons looks very chic, but it has no spaces that match the grandeur of this room.

Unfortunately, the Lobby was the only place where service at The Peninsula faltered. At breakfast, the overwhelmed staff did their best, but service was terribly slow, our food was none too warm when it finally appeared, and we had to ask for things like salt, pepper, butter and jam that should have arrived automatically. At the less-crowded Four Seasons, service at breakfast was faultless, and the personable waitstaff often addressed us by name.

Our experiences in The Peninsula’s other dining venues were much better, notably at Shanghai Terrace, a high-end Chinese restaurant with a cozy dining room and large adjacent terrace on the roof of the hotel. Everything we sampled was superb, including colorful “20th anniversary dumplings” (apparently filled with 20 ingredients), a halibut fillet steamed with ginger and scallion, and rich shredded duck in XO sauce with crunchy mixed vegetables.

Better views are to be had from the higher terrace of the fashionable Z Bar, which The Peninsula unveiled in 2018. Creative cocktails include unique ingredients like Mancino Sakura vermouth from Japan and Kyrö gin from Finland. Redolent of anise, lime and leather, my Patagonia Cooler cocktail was based on Träkál, a spirit made with fruits and botanicals indigenous to southern Argentina. Z Bar is understandably popular with locals, making it wise to make a reservation in advance (we did see empty bar stools seemingly available for walk-ins). Do so through the concierge, rather than the bar’s website, which will require you to make a $50 per-person deposit that is applied to the final bill.

The bar at the Four Seasons has no terrace — the hotel has a dearth of outdoor space — but reservations aren’t as necessary. It was busiest with the after-work crowd, thinning out around dinner time. I very much enjoyed the bar’s fragrant and strong O.T.O.F. cocktail, an unexpected combination of George Dickel rye, Old Tom gin and cardamom syrup. We sipped our drinks as a DJ spun some lively funk and remixed disco at a volume refreshingly conducive to conversation. It was quite a different scene from the staid and clubby bar the Four Seasons used to have. Service in general at the Four Seasons used to be unwaveringly formal, with the staff in sharply tailored suits. For many of the men, the jackets have come off, and a number of employees sported eye-catching jewelry and other accessories that formerly would have been taboo. Staff at The Peninsula, in contrast, maintain a consistent sense of classic formality in both manner and appearance.

The other public spaces we enjoyed were the indoor pools, which were also quite different from one another. At The Peninsula, we had to make reservations to use the pool and adjacent sun deck, whereas none were necessary at the Four Seasons. But The Peninsula’s is more impressive, with its double-height windows overlooking Michigan Avenue, and guests can order food and drink. The Four Seasons’ (unrenovated) pool has a striking cylindrical skylight but no view, waitstaff or terrace.

View from our Lake-View Executive Suite, Four Seasons, Chicago - Photo by Andrew Harper editor
Bedroom of our Lake-View Executive Suite, Four Seasons - Photo by Andrew Harper editor
Sitting area of our Lake-View Executive Suite, Four Seasons - Photo by Andrew Harper editor
Bath of our Lake-View Executive Suite, Four Seasons - Photo by Andrew Harper editor
Swimming pool, Four Seasons Chicago, Four Seasons - Photo by Andrew Harper editor
Lobby, Four Seasons Chicago, Four Seasons - Photo by Andrew Harper editor

And, of course, the rooms at the hotels have their various advantages. We booked a City-View Executive Suite at the Four Seasons, but because our rate included an upgrade on arrival if available, we ended up in a Lake-View Executive Suite. Frosted-glass doors divided the living room and bedroom, both of which had views of the art deco Palmolive Building and azure Lake Michigan. The spacious living room had a navy velvet sofa and armchair and a dining area with two mocha-toned faux-leather chairs. The minibar was empty of food, drink and serving ware — COVID — but we could request any item formerly inside it with no delivery fee. In the bedroom, the king-size bed was predictably sumptuous, but the curtains did a poor job blocking the light of the sun rising over the lake. The bath of polished limestone had one vanity, a soaking tub and a small separate shower, the latter set off from the other elements, chopping up the space but adding more privacy.

At the Four Seasons, frosted-glass doors divided the living room and bedroom, both of which had views of the art deco Palmolive Building and azure Lake Michigan

Our Grand Premier King Room at The Peninsula cost about $60 more, but it was smaller, and it overlooked Michigan Avenue rather than the lake. Nevertheless, it felt very plush, with a broad work desk with a faux zebra-wood veneer, off-white leather chairs and an ivory linen sofa backed by a stylish swath of floral wallpaper. Here, too, the king bed was divine. Although the room hadn’t been renovated as recently — I spotted a few nicks and dings — the technology felt up-to-the-moment, with no fewer than three tablets that had intuitive controls for the lighting, climate and television. And in the more open-feeling bath, there was a second television mounted over the tub. The minibar came fully stocked with snacks, dishes and glasses, and the room had more storage, since the hall leading to the bath doubled as a walk-in closet.

We ordered club sandwiches from room service in both accommodations, and they both arrived in about a half hour. At the Four Seasons, the fries were a bit limp and the ketchup came in packets, whereas at The Peninsula, the fries were crisp and the condiments came in more-attractive little bowls. But I couldn’t feel too annoyed about the fries at the Four Seasons as we gazed at the beautiful lake right out our window.

All things considered, I still give The Peninsula the edge over the Four Seasons, but just by a nose. We had a marvelous time at both hotels. The Four Seasons gave us more square footage for the money and better views, and we had a better experience with its concierge. The Peninsula had grander public spaces, a slightly more formal service style and a more glamorous accommodation. One or the other might suit your needs and personality better, but in the end, it’s a win-win.

- Hotels at a Glance -

The Peninsula Chicago    95Andrew Harper Bird


The staff’s polish; the grandeur of public spaces such as the Lobby and the indoor pool; the various outdoor spaces; the refined Shanghai Terrace restaurant; our Grand Premier King’s rather glamorous décor and beautiful bath.


The general lack of lake views; the necessity of making reservations for the only bar in the hotel; the overwhelmed staff.

Good to Know

The hotel can arrange a three-hour architectural tour aboard a private 48-foot yacht.

Rates: Grand Premier Room, $760; Executive Suite, $1,000
Address: 108 East Superior Street
Telephone: (312) 337-2888

View The Peninsula Listing

Four Seasons Chicago    94Andrew Harper Bird


The sleek look of the renovated public areas; the new liveliness of the bar-lounge; the many lake-view accommodations; the fine new restaurant; the highly personable service; the impressive concierge.


The spa and pool areas could still use some freshening; the general lack of outdoor space.

Good to Know

The complimentary kids’ club is temporarily unavailable, but the “Ice Cream Man” will still make in-room deliveries.

Rates: Lake-View Executive Suite, $1,020; Premier Suite, $1,700
Address: 120 East Delaware Place
Telephone: (312) 280-8800

View Four Seasons Listing

Waldorf Astoria Chicago

Main entrance, Waldorf Astoria
Main entrance, Waldorf Astoria - Photo by Andrew Harper editor

Always on the lookout for something new to recommend in Chicago, I evaluated three other hotels in the River North and Gold Coast neighborhoods. Of these, I liked the 215-room Waldorf Astoria best. A bit tucked away on Walton, a block from Oak Street’s designer boutiques, the hotel’s courtyard entrance has a Parisian feel. A starburst of a chandelier presides over the gleaming lobby, done in chrome and black-and-white marble. Aside from the lobby’s coffee shop and the Brasserie restaurant (closed during our stay), the hotel’s other main public space is its expansive spa and fitness center. The pool in the latter is narrow but long enough for laps. A few floors up, our Deluxe Room could easily have passed for a junior suite, and it was exceedingly comfortable, with cushy velvet armchairs and a fluffy bed. The design of the marble bath (with a separate shower and tub) echoed that of the lobby, and it was fun to watch the television in the mirror as I brushed my teeth.

Our Deluxe King Suite at the Waldorf Astoria Chicago - Photo by Andrew Harper editor
Bath of our Deluxe King Suite - Photo by Andrew Harper editor
Swimming pool - Photo by Andrew Harper editor
Outdoor café - Photo by Andrew Harper editor

Many of the accommodations at the Waldorf Astoria come with furnished balconies in addition to gas fireplaces, but the service is not at the same level as at the Four Seasons or The Peninsula. Our experience with the “Private Bar” is a good example. Shortly before we checked in, we ordered the Sweet & Salty Snack of “trail mix, chocolate-covered blueberries and local jerky.” It was not in our room when we settled in that evening, and it took two more phone calls and 12 more hours for something to arrive. I couldn’t help but laugh when we received a salver bearing a giant bowl of pretzels, nuts and M&Ms, with no remark on the substitution. It looked like something from a college party.

- Hotel at a Glance -

Waldorf Astoria    89


The dramatic lobby; the many accommodations with furnished balconies; our spacious and well-laid-out room; the large fitness center.


The occasional service clumsiness.

Good to Know

The in-room gas fireplaces have been “temporarily unavailable” for quite some time.

Rates: Premier King With Terrace, $830; Corner One-Bedroom Suite, $975
Address: 11 East Walton Street
Telephone: (312) 646-1300

Waldorf Astoria

Viceroy Chicago

Viceroy Chicago - Photo by Andrew Harper editor
Bed in our Grand Lake View King Room - Photo by Andrew Harper editor
Floor-to-ceiling window of our Grand Lake View King Room - Photo by Andrew Harper editor
Spacious bath of our Grand Lake View King Room - Photo by Andrew Harper editor
Lounge area in the lobby, Viceroy Chicago - Photo by Andrew Harper editor

Young-at-heart sorts may want to consider the 180-room Viceroy Chicago, incorporating a new glass tower and historic brick building on Rush Street. I quite liked its warm lobby-lounge, filled with midcentury modern-style seating groups and contemporary art, and the popular rooftop bar and pool on the 18th floor. It was also a pleasure to order room service from the hotel’s excellent restaurant, Somerset. The subtly spicy crab salad on rice cakes, and the rich bone-in pork chop with chive spätzle and truffle béchamel were standouts. Through the floor-to-ceiling windows of our Grand Lake View Room, we could see a snippet of water as we ate, and the room’s eclectic pattern-rich décor was quite stylish. Nevertheless, it felt oddly compact considering its 440 square feet, perhaps because the bath, with its dual vanities and separate shower and tub, took up so much space. But my main problem with this hotel is that the staff handled our noise complaints poorly. The couple in the adjoining room had loud shouting matches during the day and made up noisily in the evening. They hosted boisterous guests until the wee hours both nights of our stay. The front desk sent up earplugs but did little else to address the problem.

- Hotel at a Glance -

Viceroy Chicago    88


The striking architecture; the fashionably eclectic décor; the excellent restaurant and room service.


Our rather cramped bedroom; the serious noise problems that went unaddressed.

Good to Know

The hotel’s website says that the AIRE Ancient Baths, a spa with which it has a relationship, is a “short distance” away, but it’s 15 minutes by car.

Rates: Grand King, $640; One-Bedroom Lake View Suite, $1,200
Address: 1118 North State Street
Telephone: (312) 586-2000

Viceroy Chicago

21c Museum Hotel Chicago

21c Museum Hotel Chicago - Photo by Andrew Harper editor
First gallery of the hotel's museum - Photo by Andrew Harper editor
Living area of our Corner Suite - Photo by Andrew Harper editor
Bedroom of our Corner Suite - Photo by Andrew Harper editor
Bath of our Corner Suite - Photo by Andrew Harper editor
View from our Corner Suite - Photo by Andrew Harper editor

Although I knew it wasn’t really a luxury property, I was curious to try the new 297-room 21c Museum Hotel Chicago. This small chain known for rotating exhibitions of contemporary art has branches in cities such as Louisville and Cincinnati, where there is limited high-end hotel competition. At check-in, we were alerted that there were no bathrobes nor extra towels in the room, “because of COVID.” I had some sympathy for the hotel’s stringent (if unscientific) protocols until a maintenance man came to repair our room safe. He twice removed his mask to speak to us. 

Unfortunately, though our Corner Suite had a spacious separate living room, ample natural light and an attractive white-tile bath with bronze fixtures, it felt colorless, verging on institutional. Even had the suite been beautiful, the staff’s poor communication would have sunk the hotel’s chances at a recommendation. I eventually discovered that bathrobes and extra towels are available on request, for example, something they neglected to mention at check-in. Also unmentioned was the “Urban Fee” of $20 per day, giving us Wi-Fi, access to the spa (closed during our stay) and entry to the museum (free to all in any case). When I complained that much of what the fee covered was already free or unavailable, it was removed from our bill.

And then there was the museum itself, occupying much of the first two floors of the hotel. The curator had an obvious ax to grind, resulting in an exhibition at once strident and boring. Banal, simplistic and preachy objects outnumbered well-considered works by notable artists. If you agree with the artists’ politics, you’ll likely enjoy the exhibition, and if you don’t, you won’t. If only the 21c Museum Hotel had put as much effort into its service as its sermonizing.

- Hotel at a Glance -

21c Museum Hotel Chicago   86


The convenient River North location; the size of our suite; the quiet atmosphere.


The staff’s poor communication; the irritating “Urban Fee”; the various arbitrary COVID protocols; our suite’s institutional feel; the depressing art exhibition.

Good to Know

The hotel is a short walk from Eataly and the world’s largest Starbucks.

Rates: Deluxe Queen Suite, $480; Corner Suite, $500
Address: 55 East Ontario Street
Telephone: (312) 660-6100

21c Museum Hotel

Read more about our editor’s trip to Chicago

By Andrew Harper Editor Andrew Harper editors travel the world anonymously to give you the unvarnished truth about luxury hotels. Hotels have no idea who the editors are, so they are treated exactly as you might be.