The Peninsula Chicago

Service

You choose the Peninsula for the service. A lot of the staff have been here for years. They remember your name, housekeeping is the best I've had in the city, and if you ask for ice once it's waiting in the room the next day without a word. You can message the hotel from your phone for anything, and extra pillows turn up in ten minutes.

Tell them what you're celebrating and they'll make something of it. Children get gifts and a scavenger hunt, and dogs get a bed, bowls and their own menu.

The weak point is the arrival. The first welcome at the street door and the front desk can be cool, and the hosts at breakfast can be brusque when The Lobby is busy. Now and then a turndown is missed or a room isn't ready on time. Once you're settled in, though, it's the most dependable service in Chicago.

Rooms

The rooms are big. Even the entry-level Superior is around 530 square feet, with a dressing area between the bedroom and the bathroom, and everything is spotless. Lights, curtains, temperature and room service all run from tablets. They take a few minutes to learn, and then they're a pleasure.

The rooms are no longer new. The hotel opened in 2001 and the rooms were last redone in 2016. The bedrooms have held up, but the bathroom is the weak spot: lovely marble and a deep tub, but one small sink, a smallish shower and a dated feel. You'll also find the odd worn socket or scuffed table. The bed is on the firm side, so ask for a mattress topper if you like it soft.

The room I'd book is the Grand Premier King, which adds a sofa and a sitting area and feels like a junior suite. If you're treating yourselves, the Executive Suite has a bathtub under a picture window looking at the old Water Tower. I'd skip the Michigan Avenue Suite, where the bedroom has no outside window.

Don't expect big views from most rooms, and do think about noise. There's a hospital and a fire station close by, so sirens come past at night. Ask for a high floor away from Michigan Avenue and you'll sleep well.

Food and drink

My favourite table is at Shanghai Terrace, tucked away on the fourth floor behind a small red door. It's a dark, lacquered, 1930s Shanghai sort of room, and I think it's some of the best Chinese food in Chicago. I'd order the dim sum and the Peking duck. In summer, ask for the outdoor terrace, with the towers lit up all around you.

The Lobby is the tall, bright room on the fifth floor where breakfast and afternoon tea happen. Skip the buffet, which is thin for a hotel like this, and order the pancakes. It's expensive, well over $100 for two, and there's often a wait at weekends unless you go early. Dinner is only served some nights at the moment. From early 2027 the room becomes an Italian restaurant called Comunità in the evenings, with handmade pasta and a huge Florentine steak, which should fill that gap.

Pierrot Gourmet, the cafe on the corner, is where I'd go for a croissant or a tartine, and a breakfast credit works there too. Z Bar, the rooftop bar, has a great terrace over Michigan Avenue and good cocktails. It's also loud, small for the crowd it draws and uneven on service, so I'd go early for one drink before dinner.

Setting

You're one block off Michigan Avenue, right by the old Water Tower. The shops are at the door, Oak Street Beach is a short walk, and the river and the architecture boats are about fifteen minutes on foot. For a first visit to Chicago I think it's the easiest base there is. The best restaurants are a taxi ride away in the West Loop, and the river views belong to other hotels.

The building takes some getting used to. You arrive at a small street entrance and take a lift to the lobby on the fifth floor, then another to your room, and those lifts are slow. There's also no real lobby lounge to sit in with a drink, which I miss.

The reward is at the top. The spa, gym and a 25-metre pool have the nineteenth and twentieth floors, behind walls of glass, with a hot tub and a sun terrace outside for summer. It's a lap pool, bright and calm, and an early swim up there is the thing I'd miss most. The spa was refreshed in 2025 and the treatments are excellent, though it's popular with local members and there's a steam room but no sauna. In winter a small skating rink goes up on the fourth-floor terrace, and children love it.

Value

Chicago is cheaper than New York or London, and the Peninsula is often better value than you'd guess. In the cold months I've seen rooms from around $400 to $450 a night, which is a bargain for this much hotel. For most of the year it's $600 to $700, and a holiday weekend in summer can reach $1,200. Third-night-free offers come up often.

The extras add up. Valet parking is about $80 a night, so don't bring a car, and breakfast and drinks are priced like the room.

Book this one direct or through an advisor, not through a discount site. Either way you get the hotel's flexible timing, which lets you check in from 6am and leave as late as 10pm when they can manage it. An advisor usually adds breakfast for two, a $100 hotel credit and an upgrade when there's one to give.