The Drake

The Drake’s history is part of what made this stay memorable. Photos around the property and in our suite showed past celebrity, political, and royal guests in their prime. We loved being part of the hotel’s storied legacy. Its location by Lake Michigan was phenomenal. During a sudden spell of mild February weather, it was fun watching locals walk, jog, and play volleyball on the beach. A 20-minute stroll along N. Michigan Ave takes you to the Riverwalk and Wrigley Building. We were celebrating a birthday on a satisfying three-night stay, and the team went above and beyond to make it memorable. The upgrade was very generous, and staff were cordial and helpful throughout. We were treated like VIPs. As a Hilton Honors Diamond member who earns his status through actual stays, I can honestly say The Drake ranks among the best Hilton properties I’ve visited. My companion and I stayed at a number of great Chicago hotels, but The Drake left a lasting impression.

The Gold Coast Room looked absolutely incredible on our wedding day, and the cocktail hour in the Palm Court room was lovely. The team stayed on top of the timing, details, and everything we envisioned. The Drake was easy to work with and met every request and idea with sincerity and effort. We feel beyond blessed to have celebrated there. We toured about 30 Chicago venues, yes, I know that’s crazy, and I’d been leaning against having a hotel wedding. A friend suggested The Drake because her parents had married there and it felt like “classic Chicago.” From our first tour, we were greeted warmly and treated with genuine kindness and attention to detail. My fiancé and I were won over, knowing our guests would get the same care during the wedding weekend. The sales catering, banquet, and chef teams were fantastic. At our tasting we met the head Chef and Jorge, the banquet team captain. My parents and we absolutely loved Jorge. He was charismatic, attentive, and fun to be around, and we trusted him and his staff to care for our friends and family. They did. I remember seeing my parents’ table cheer “Jorge! Jorge!” as he came around with the champagne, because he felt like a friend of the family. WOW WOW WOW, the service, food, support, and whole experience blew us away.

We got a suite in the end, after I asked to speak with the manager, who was nice, but that room was filthy too. I was there with my wife for her birthday, and the first room had hair all over the bathroom and used coffee supplies left behind. I called the front desk, but nobody came. The next day a housekeeper was sent up; I checked and found a wad of hair in the tub. Back downstairs, a young woman at the desk seemed mildly amused when I complained. The whole building looks neglected. Wallpaper is coming loose in the lobby, parts of the lights are missing, and the carpet is awful. I last visited about 30 years ago for a wedding, and it's disappointing to see this iconic hotel deteriorate. Hilton should be ashamed. Chicago isn't what it used to be, I left so disappointed I wouldn't stay here even for free.

The friendliest people we dealt with were the valets, who were outgoing and genuinely gracious. That was the best part of the stay. Check-in itself was easy, but the service elsewhere often fell short. We came with family to revisit a place that used to be our Chicago go-to, and the room had plenty of space and great views. Still, it was in terrible shape: peeling, stained wallpaper, marked walls, obvious water damage, leaky faucets, and patchy repairs. It smelled overwhelmingly damp, with what seemed like a hidden grocery store air freshener trying to cover it up. The glasses in the hall kept piling up for days, and fruit flies were there whenever we stepped outside. The public areas, especially the famous lobby, were mostly maintained, but the rest of the hotel and its service standards seemed left to decay. The bar was open while people were enjoying tea in the lobby. When we stopped for a cocktail, the bartender brushed us off and said they were closing soon and mainly made Bellinis for old ladies having tea. We went downstairs instead. It wasn't very busy, the staff were pleasant, and the drinks took a while but were fine. Getting the bill meant searching everywhere for the server. On another cocktail visit, the bartender showed little care for the job or customers. I had to ask repeatedly for a twist in my martini; it was finally dropped in by a bare hand, with an unwashed piece of fruit that still had its produce sticker on it. It floated to the top, and the bartender saw it but didn't seem bothered. It's a shame to see an iconic place fall so far in both operations and service. This visit came nowhere close to the quality we remembered.