We’ve partnered with Plufl, the world’s first dog bed for humans
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Grab your popcorn and your passport! Set jetting is your ticket to stepping into your favorite TV and movie scenes. Staypineapple cities are where iconic shows and films come to life. Pack your bags — it’s time for a reel adventure!
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Every baseball fan needs a stadium bucket list! From iconic classics to modern showstoppers, these must-visit ballparks deliver epic views, electric crowds and unforgettable game-day vibes.
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We’ve been voted one of the Best Pet-Friendly Hotels in the US by Newsweek!
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Pets stay free with our Pineapple Pup Plus One Package
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Lulu of @hansandlulu was crowned top dog in our 8th Annual Dash, The Pineapple Pup’s Costume Contest!
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We took top spots for Best Pet-Friendly Getaway two years running!
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Our partnership with Procure Impact helps support our community through thoughtful sourcing
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Unleash your creativity and enter your dog into Dash, The Pineapple Pup’s Costume Contest!
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Celebrate the special furr-iend who fills your life with happiness!
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Staypineapple Chicago ranks #3 for the Best Boutique Hotel in the nation!
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Post your pineapples for Pineapple Day to get a chance to win some juicy prizes!
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