Staypineapple Hotel Chicago – Darling Hotels of the USA

July 12, 2019

Thank you StayPineapple for inviting me to stay at your hotel. I received two complimentary nights for an honest review of the hotel. As always, all opinions are entirely my own.

Growing up in Minnesota, Chicago was a frequent destination of my friends and family members in the Midwest. Although I’ve moved from Minnesota since, I still find myself in Chicago frequently whether it be for work, a music festival, or just for fun. On my most recent trip, I came across Staypineapple, An Iconic Hotel in the The Loop. I was searching for an on-trend hotel with a location just as fantastic as the price. Staypineapple fit that description perfectly.


1 W Washington St, Chicago, IL 60602

Staypineapple is ideal when it comes to getting around Chicago. The location is just a couple blocks from Millennium Park {on the side with The Bean, no less}. It’s also across the street from Block 37, which is filled with shopping such as Zara and Anthropologie, and the infamous Magnolia Bakery. Across the street is Chicago’s flagship Macy’s, complete with 13 floors of dining and shopping. The hotel is also in close proximity to The Art Institute of Chicago, the Chicago River, and the Willis {Sears} Tower. If you’re using public transportation to get around the city, a train station is located just 1.5 blocks from the hotel.

Staypineapple chicago an iconic hotel the loop exterior awning street view washington st


I stayed in a Queen sized room. The room had an amazing view of the city. The mattress was comfortable, and the modern chaise lounge was a nice touch. While the room itself was on the smaller side, it was cozy vs. being cramped. The only minor drawback to the size would be the bathroom, as the pedestal style sink made it difficult to do makeup or hair in the mornings. Rooms do have physical keys instead of key cards. This did make me slightly nervous as there is much more risk to losing a key than there is a card.

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staypineapple an iconic hotel the loop chicago 14th floor queen room city view downtown


One amazing thing about Staypineapple is how dog friendly it is! As one of my friends native to Chicago pointed out, buildings in Chicago overall aren’t the most dog friendly. Your furry travel companions are welcome and encouraged at Staypineapple, where dog treats stay next to reception all day long.

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As I’ve mentioned in previous hotel reviews, service is always what makes or breaks a hotel for me. In this hotel, the front desk couldn’t have been friendlier or more willing to help. I was always greeted with a smile while entering and leaving the hotel. Any concerns I may have had were taken care of quickly and kindly.

StayPineapple chicago boutique hotel staircase the loop


Staypineapple The Loop Chicago does offer valet parking with in and out privileges. Chicago is a notoriously difficult city to find parking in, so I highly recommend you valet your car should you decide to drive to the city. The hotel offers Park and Play packages for savings should you decide to do so! Although service inside the hotel was relatively quick, valet did seem to be a little slow, taking 30-45 minutes to retrieve the car on a few different occasions.


So. Many. Pineapples. No piña coladas, though. The pineapples are a fun and quirky touch that add to what makes this hotel unique. In the afternoons, Staypineapple sets out pineapple treats such as pineapple cupcakes for hotel guests. You can also expect to find pineapple-infused water by reception. In your room, you can find a pineapple shaped USB charging station. The hotel also has yellow pineapple bikes which you can take out and cruise around the city in, which are a lot of fun as well. These fruity touches make Staypineapple stand out amongst hotels in Chicago at this price point.

staypineapple hotel pineapple usb charging port dock


For being so compact, this hotel packs in some great amenities. Workout in the Staypineapple fitness center, or stream all day long with Streampineapple. Grab lunch or dinner at the Atwood, Staypineapple’s in-house restaurant. Staypineapple also offers high speed internet to unlimited devices, a huge plus if you’re someone like me who travels with several. Note that a $15 + tax amenity fee per night does apply to all reservations.

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If you’re looking for a fun and unique place to stay in Chicago at an affordable price point, Staypineapple fits the bill perfectly! The hotel features beautiful, unique architecture that is rare in hotels in major cities these days. It made for some great Instagrammable moments! I was thoroughly impressed with the service and location of Staypineapple, an Icon Hotel in The Loop Chicago. If you’re someone who finds yourself needing a bit more space in a hotel whether it be the room itself or the lobby area, this may not be the perfect fit. This hotel is ideal for solo travelers and couples as it is cozy.



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About Me

Eva Phan of Eva Darling paris france tarik ediz gown newyorkdress eiffel tower trocadero best paris photo location

Hi, I'm Eva! I'm best described as an aspiring Blair Waldorf with a case of the travel bug that can't be cured. I'm a lover of witty words, pink peonies, and slight sarcasm. I aim to empower women to travel the world solo, sharing on-trend, feminine style inspiration along the way. Originally from the Minneapple {Minneapolis, Minnesota}, and now living in the Big Apple, you can probably find me most often on a plane, running down Park Avenue stressed out in 4" heels, or planning my next escape. Click on the photo to learn more.

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