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    Staypineapple, an Iconic Hotel, the Loop

    Staypineapple, an Iconic Hotel, the Loop welcomes two dogs of any size for an additional fee of $25 per night. Dog treats, bowls and beds are available, but dogs may not be left in the room unattended. There isn't a pet relief area on site, but there is a grassy area a few blocks from the property and a dog park within walking distance. Cats are not permitted. For same day arrivals, please call 877‑411‑3436 to confirm availability of a pet-friendly room.
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    Booking Options

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    $351
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    $352

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    Description

    In a city chock full of awesome—cuisine, art, architecture, shopping—we proudly offer Staypineapple, an Iconic Hotel, the Loop just steps from Millennium Park. Not to be outdone by the amazing city around it, the hotel is housed in a National Historic Landmark building and is the perfect jumping off spot for exploring downtown Chicago. In the Loop and with the Theater District just steps away, you are poised to take full advantage of all the city has to offer. Whether it’s a warm, summer day or a teeth-chattering winter white-out, every day will be a spectacular one. All of our rooms and suites feature historic touches original to the building while also offering every modern amenity: high-definition TVs, high-speed Wi-Fi and mini fridges. It’s your Windy City oasis.

    Amenities

    • Pet Friendly
    • Gym / Fitness Center
    • Free WiFi
    • Meeting Rooms
    • Air Conditioning
    • Heating
    • Restaurant
    • Parking Available
    • Wheelchair Accessible
    • Dry Cleaning
    • Elevator
    • Non-Smoking Property
    • Bicycles

    Reviews

    BringFido Guest Rating
    TripAdvisor Traveler Rating

    Staypineapple, an Iconic Hotel, the Loop has received a rating of 4.5 out of 5 bones by 4 canine critics on BringFido and 4.5 out of 5 by 2,971 guests on TripAdvisor.

    • Monica
      Aug 26, 2023
      Great for big dogs!

      We recently stayed at Staypineapple in Chicago when our AC went out on 100° days! :/ I cannot recommend this place enough. The honored my request for a quiet room because I have a couple nervous pups when it comes to noises outside of the room. They have pup packages that include a dog bed, water bowl, poop bag dispenser and treatos! Everyone was so nice and welcoming to both us and the pups. They also don't have size restrictions so we were able to stay with our big boy.

    • Magdalene Mae
      Jul 16, 2023
      Perfect weekend

      Booked the room so we could have a relaxing place to stay after a day at Montrose Dog Beach. Unfortunately, it started pouring & we had to cut our beach day short. I was worried about checking into a hotel drenched & covered in sand, but everybody was so very friendly & helpful; checking in was a breeze & they helped me with things before I even knew I needed help with them! The front desk, the valet, the cleaning crew! Everybody! They were so, so sweet to my dogs- treats all the time! (My youngest dog became wise to this & would beg to go outside just so she could walk around the corner & come in the front door to get attention & treats.🤣 They also catered to my caffeine addiction & loaded me up with extra coffee. The bed, pillows & duvets are like a cloud; even the robes & bath towels are ridiculously soft.
      Definitely going to be back - make it a summer tradition. Can’t wait to check out the other locations🍍

    • Naotaka
      Sep 19, 2021
      Great hotel

      Very clean and pleasant hotel at the center of Chicago. We had a good stay with our 2 dogs.

    • Kelsey
      Dec 7, 2019
      No Potty Area

      This is a great hotel except there’s no where for pups to potty. We had to walk ten minutes so my pup could relieve himself.

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    Health & Safety

    Safe Stay: Staypineapple, an Iconic Hotel, the Loop has enhanced cleaning and safety measures in place. Hand sanitizer is provided to guests, and rooms are disinfected between each stay. Cashless payment is available. This property does not require health documentation at check-in.

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    Book with Confidence

    • This hotel’s pet policy has been confirmed by our editors and your reservations will be backed by our no-hassle .
    • Our Canine Concierge will make sure you’re assigned to a pet friendly room, so there won’t be any unpleasant surprises at check-in.
    • And you’re getting a great low rate too! We never charge a booking fee on top of the special negotiated nightly rate.
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    Staypineapple, an Iconic Hotel, the Loop