Honest Review of Staypineapple Hotel in Chicago

The first time I went to Chicago I was a kid so I could not choose my hotel and in all honesty, I don’t remember where we stayed. For my most recent visit, I got to choose where we stayed and I am very happy with our choice of Staypineapple Hotel in Chicago. It’s a 4-star hotel in a historic building with a prime location near the Magnificent Mile. It was easy to get to, near public transportation for the city, and had all the amenities we could ask for. It was perfect for our walking tours of Chicago since it was centrally located!

This review of Staypineapple Hotel in Chicago will give you all the details – what’s breakfast like and how big are the robes? As usual, I don’t use Photoshop, so what you see is what you get!

We spent four nights at the hotel during our three days in Chicago. Thank you Staypineapple for working with me to stay at your hotel. As always all opinions are entirely my own.

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Location

Address: 1 W Washington St, Chicago, IL 60602

The first thing I noticed about Staypineapple Chicago is the ideal location, especially for a first-time visit. The location is just a few blocks from Millennium Park home of the Bean. You’ll also find plenty of shopping nearby with Anthropologie and Zara across the street in Block 37. Unfortunately the infamous Magnolia bakery (which was recommended by the friendly front staff at StayPineapple a few times.)

It’s also about one and a half blocks away from public transportation including the elevated train “the L” and the bus! We loved using public transportation to get around the Windy City!

We landed at Midway International Airport, which was the closest airport (and for us where we got our cheap flights to). We just took the orange line to the Washington/Wabash stop and walked the block and a half to the hotel.

Checking In

Checking in to Staypineapple Chicago was a breeze. Even though we got in at 10:00 p.m. The front desk staff was incredibly friendly and welcoming. You receive a real key instead of a key card. If you lose the key, there is a fee because the hotel and the keys are historic. We only got one room key for the two of us. The staff also walked us through the amenities and explained the pineapple hour, which we will get into below.

Staypineapple Parking & Valet

Chicago like any major city is difficult to find parking in so if you’re bringing your car valet is often an option. Staypineapple Chicago does offer valet parking. They do have in and out privileges so it’s easy to come and go. We did not have a car with us so I can’t speak to the speed and service but the location of it was right in front of the hotel. Visitors beware though trying to find street parking in the neighborhood “The Loop” which is where Staypineapple Chicago is located may be difficult and more expensive.

History of the Hotel

One of the coolest things about Staypineapple Chicago is that it’s a National Historical Landmark. It was originally a First National Bank before the Chicago fire of 1871, which it survived. Rooms

After the fire, it was built up to be a skyscraper and was completed in 1895. Before Staypineapple’s opening in 2011, it was a retail and office space.

There’s even a time capsule from 1999 in the lobby of the hotel that will be opened in 2099.

Our Room

Our room was a king-size suite. We had a small bench at the end of the bed and the second room had a couch with a coffee table in there and a desk for working. There was a TV in each room. The only minor drawback to the room was that the double doors that open into the bedroom couldn’t fully open. One of the doors hits the bed.

The Bed

Staypineapple’s motto is “get naked”. They want you to feel as uninhibited in their rooms as you do at home. A major part of this is the room’s cleanliness and comfort. I fell in love with the fluffy duvets that they had on their plush king bed. There were two so Spencer and I were not fighting over the duvet during the night.

The bed was soft but not too soft with a total of five pillows on the bed. If you would like more you can ask at the front desk.

Air Conditioning

We love it cold at night, so having great air conditioning is a must for us! The dial was really easy to use and no card was required to stay (typical in Europe). However, please be mindful to turn up the temperature when you leave the room to save on energy!

Mini Fridge

Underneath the TV in the sitting area, there was a storage cabinet that included a mini fridge, Keurig cups, sugar, and two Pineapple mugs for your use. There was also real cream in the refrigerator which really impressed me. I am so used to hotels only having powdered milk which I’m not a fan of in my tea. The mini fridge was large enough to hold a bottle of wine plus snacks.

Storage

There was plenty of storage in the room. There was an armoire as you entered the room, drawers underneath the TV in the bedroom, and a few drawers in the desk. There was also a luggage rack that we were able to put our suitcase on for the weekend. If you are traveling with a family our room may not have been big enough for everybody however since there were only two of us, it was plenty of room.

The Bathroom

I found the bathroom to be a little small. Closing the door while attempting to use the toilet was awkward. The shower and tub were a good size though. There was a full-width mirror and a makeup mirror available. The countertop was large enough to fit all of our personal items as well. Staypineapple Chicago had dispensers for hand soap, lotion, shampoo, conditioner, and body wash. I liked that they were more eco-friendly by not having mini-plastic bottles.

Water Pressure

The water pressure in the shower was great. The water also got very hot. The showerhead could be changed to different water pressures for your liking.

The View

The view from our suite was absolutely breathtaking. We were down the road from the famous Chicago theater, so Dash and I got to enjoy the view with our morning tea from the Keurig.

Each window had blinds and then full-length curtains. Two of our blinds were broken but the curtains worked. They did not keep out the morning light, so if you’re a light sleeper (like me) bring an eye mask!

Hotel Amenities

Pet Friendly

While I did not bring a dog on this trip it is lovely to see a dog-friendly hotel. Many buildings in Chicago are not dog-friendly. Not only are there treats at reception every day but there is also Dash, a stuffed husky that is in everyone’s room to greet you. If you decide to adopt him for $25 part of that money goes to a local animal rescue organization.

Bikes

Chicago is actively working to become a very bike-friendly city – and Staypineapple Chicago is joining in on the fun! They have bikes available for guests to use for free. They even have helmets and locks for your use. We got to enjoy riding them near Millenium Park, down to the Art Institute of Chicago, and even to Shedd Aquarium. Bike riding is a great way to see Chicago in spring. I do suggest bringing gloves and ear warmers – it can get a little chilly with the breeze!

“Pineapple Hour”

One of the most unique things about Staypineapple Chicago (and all Staypineapples) is Pineapple Hour. Every afternoon between 3:30 and 6:30 pm there is pineapple water and pineapple cookies available for free as an afternoon snack.

We were only able to partake one afternoon, but we combined it with our free drink at the bar for a perfect mid-afternoon break. When you check-in, each guest is given a coaster for a free drink at the bar (house wine, draft beer, or nonalcoholic soda).

The Bar

The bar has a very clean 1920s feel since it’s part of the Atwood Restaurant. (Which we did enjoy breakfast at below). There were two televisions at the bar for casual viewing. There were also couches for more comfortable seating areas. There were happy hour specials for both drinks and food available.

Breakfast at Staypineapple Chicago

We got breakfast at the Atwood Restaurant on our last day before heading back to the airport. While there was enough variety that we were happy, there weren’t a ton of options. There was the usual build-your-own omelet, breakfast sandwich, American breakfast, a breakfast burrito, waffle, greek yogurt parfait, and oatmeal available. They had sides as well including breakfast meats and potatoes.

Robes

This was my favorite thing! Their microfiber robes were SO comfortable. Bonus: they fit with extra room for those of us who are plus-size! We loved relaxing in them at the end of a busy day. You can even buy them on their website!

Wifi

The wifi was great! StreamPineapple allows you to stream your favorite shows and music in your room. We had no issues with the wifi!

Fitness Center

While I didn’t use the fitness center (hitting 20k steps a day in Chicago will make you not want to), I did check it out. There was a small weightlifting area and a few cardio machines available!

Bonus Points!

I left my passport and Kindle Paperwhite in a drawer in the nightstand next to the bed (which I noticed at the airport an hour before our flight). Luckily I didn’t need it for the flight since we flew domestically. The staff at Staypineapple Chicago was nice enough to mail it back to me. It even came wrapped in bubble wrap and a packing pillow so there was no damage.

Overall Thoughts

I loved staying at Staypineapple Chicago. The building was historic and even survived the Chicago fire It had a great location in the Chicago Loop, and had everything we could want from a hotel. I also loved having the bikes available to explore Millennium Park and Shedd Aquarium. The friendly staff make your stay here a special one! I highly recommend this hotel to anybody.

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