Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop Overview

First Impressions

Walking into Staypineapple, An Iconic Hotel, The Loop, you immediately get that “this is exactly where I want to be” feeling. The lobby has this perfect balance of modern comfort without trying too hard to be trendy — honestly, it’s refreshing after seeing so many hotels that feel like they’re competing for Instagram likes. What really struck me was how the staff seemed genuinely happy to see guests, not just going through the motions you get at some four-star properties.

Prime Chicago Location

You know what’s amazing about this spot? You’re literally at 1 West Washington, which means you’re in the absolute heart of Chicago‘s Loop district. I mean, step outside and you’re surrounded by everything — the Art Institute is a quick walk, Millennium Park is right there, and the shopping on State Street is basically at your doorstep. Couples especially seem to love this location (they rate it 9.7, which honestly makes total sense), and I can see why. You can walk to dinner, catch a show, or just wander around without needing to figure out transportation every time you want to do something.

The Room Experience

Here’s where this hotel really shines — the beds are absolutely incredible. I’m usually pretty skeptical when hotels brag about their bedding, but this place actually delivers on the comfort front. The room itself has this clean, uncluttered vibe that somehow feels both sophisticated and cozy. The windows give you great views of the city (depending on which side you’re on), and there’s enough space to actually unpack and settle in, which isn’t always a given in downtown Chicago hotels.

Practical Perks

One thing that surprised me was the parking situation — they actually have private parking available, which is honestly a game-changer if you’re driving into the city. Most Loop hotels either don’t have parking or charge ridiculous rates for valet service. The whole pineapple theme throughout the property is quirky without being overwhelming — it’s their signature thing, and they do it with just the right amount of playfulness. The elevators are quick (important when you’re on higher floors), and the WiFi actually works well, which seems basic but you’d be surprised how many places mess this up.

Why Guests Love It

What really sets this place apart is how it manages to feel both central and peaceful. You’re in the middle of everything Chicago has to offer, but when you come back to the hotel, it doesn’t feel chaotic or overwhelming. The combination of that prime location, genuinely comfortable accommodations, and staff who seem to actually care about your experience creates something special. It’s the kind of place where you can have a full Chicago experience without constantly worrying about logistics — and honestly, that’s worth a lot when you’re trying to enjoy a trip.

Staypineapple, An Iconic Hotel, The Loop Accommodations

Reviews of Staypineapple, An Iconic Hotel, The Loop

• Viliam from Czech Republic (9/10)

  Central located hotel. Well positioned with walking access to park, lake and all interesting parts of the city. It is also stylish as it is a bit old school – which feels very personal.
  The staff is particularly friendly and helpful.

• Russell from United States (9/10)

  Stay Pineapple is our go to place to stay in the Loop. Fantastic location, cool decor, and really comfortable.

• Rowena from United Kingdom (9/10)

  Beautiful setting and decor. Comfortable beds. Location is excellent.

• Victoria from United States (9/10)

  I love the location and the old school feel of the hotel.

• Mendelsohn from United States (9/10)

  All the pineapple touches!

• Emily from United States (9/10)

  Location. Lobby bar/restaurant. Afternoon cofee/snacks. Bedding.
  Not a cookie-cutter chain hotel, but something with character.

• Moosie from United States (9/10)

  The bedding and the room were amazing. I love the whimsical nature of the hotel. That naked feeling… It's fun 🙂

• Ciara from United Kingdom (9/10)

  Great location, nice decor, comfy beds

• Caroline from Netherlands (8/10)

  Location was amazing! Service as well

• Tim from United States (8/10)

  Location, solid and beautiful building, water policy.

Facilities