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First rate comfort & style in the Second City

Staypineapple Chicago

Whether it’s a warm, summer day or a teeth-chattering winter white-out, Staypineapple Chicago will make every day 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.

(Not So) Standard Rooms

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Accessible Rooms

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