Staypineapple, An Iconic Hotel, The Loop

The staff really made my stay. They were friendly and engaging, and when I had to wait for a car, I watched them welcome guests, chat with them, remember them, and check in on them. I also loved the personal touches: a welcome note at check-in, a refillable water bottle, the comfiest beds ever, and really nice bathroom linens. The building is super cool and truly iconic, just like the title says. I had an epic Chicago weekend and am so glad I stayed at the Stay Pineapple. The location is incredible, with plenty of shopping, museums, and theater within walking distance. I'll be back!

I really appreciated being able to leave my bags after checkout, since it gave me a few extra hours to see the city. The location is great for transit and walking. I didn't need an Uber until I left with all my bags. There's everything you need within a block, but it's definitely worth exploring farther out too. The hotel is beautifully decorated and maintained, and it respects the building it's in. As someone who appreciates architecture, I thought it was gorgeous. It's an older building, so there might be some minor quirks or things that need attention, but I didn't run into any problems. I booked over the phone because the website was glitching, and the woman made it easy. Watch out, the hold music is catchy. The rooms are clean and comfortable, and the bed and duvets were so cozy I spent more time in bed than going out early in the cold. The gentlemen at the front desk were courteous and friendly, and check-in and checkout were a breeze. I wish I could've stayed longer, but, you know... responsibilities. If I'm back in town and the location works, this would absolutely be my first choice to see if there's a room available. I'd recommend it!

I've always found Hotel Pineapple clean and peaceful, conveniently close to everything, with staff who make it feel welcoming and comfortable. It's my favorite place to stay when I visit San Francisco. On this trip, my plans were unexpectedly delayed by a full day, and Nixxy and Brian helped me find safe, secure, comfortable accommodations while I sorted out rebooking. Their kindness, professionalism, and genuine care made a stressful situation so much easier. I'll always stay here because of them. Hotel Pineapple gives you a truly exceptional experience.

We've stayed at Staypineapple three times, including with our wedding party last year, and it's been great every time. The staff are friendly and helpful, and they made things easy for the wedding group as well as during our most recent visit. The rooms are clean and comfortable, and there's a fun vibe that feels different from an ordinary hotel. The comforters and robes are seriously soft and cozy, and the pineapple-shaped sugar cookies are a great touch. It's one of our go-to places now, and we'd definitely recommend it.