Staypineapple Chicago was named one of the Best Boutique Hotels in the nation for a second year in a row!
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Staypineapple hotels are on top once again — amazing guest reviews say it all!
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We’ve been voted one of the Best Pet-Friendly Hotels in the US by Newsweek!
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2024 Most Pet-Friendly Hotel Brand
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Staypineapple for the win!!
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2023 Travelers’ Choice Award Winner
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