GOTTA GETAWAY + PLAY SWEEPSTAKES - Enter for a chance to win a 3-night stay at any Staypineapple hotel + a Nintendo Switch™ Prize Pack.

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Check out a Nintendo Switch™ — OLED Model system & play fun and exciting Nintendo Switch games during your stay.

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A Hotel for Huskies just minutes from UW campus. Check out our serious style, colorful motif, and a range of upscale amenities.

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SAVEPINEAPPLE

Staypineapple Chicago

You know a good deal when you see it (you’re smart that way). Check out our special offers at Staypineapple Chicago. Each one comes with unrivaled hospitality, stylish furnishings and comfortable amenities you’ve come to expect from a Staypineapple hotel.

Your next great Chicago adventure awaits. Start packing.

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3rd Night Free

Stay 2 nights and get the 3rd night free. Stay longer, sleep in later, and enjoy more time away. You deserve it!

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Pop Goes The Celebration!

Enjoy a bottle of sparkling wine on ice and an assortment of artisan truffles delivered to your room! Plus Free Parking*

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Pineapple Pup Package

There’s no need to ruff it without your furry friend. Bring your pup and we'll give you 50% off our daily pet fee.

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Auto Club Rate

Auto club member? Save now on a Staypineapple room.

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Young at Heart

Are you an AARP member? Take advantage of exclusive savings now!

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Government Per Diem - Uncle Sam Special

Enjoy a special rate if you work for the US government