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



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.

A Large Crowd Of People Sitting On The Sidewalk In Front Of A Building

Thanksgiving Day Parade Package

Start Thanksgiving Day with a Parade! This special package includes mini binoculars, popcorn and hot cocoa!

A Small Child jumping On A Bed

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!

A Man And A Woman sitting on bed with a dog.

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*

A Dog That Is Lying Down And Looking At The Camera

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.

Couple with yellow bikes on hill top

Park and Play Package

It’s a hassle finding parking! Put your mind at ease knowing we have a spot for you and it’s 50% off when you book this deal.

Dog driving a car

Bark and Park Package

Enjoy 50% off our pet fee and parking rate!

Small dog driving toy car

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!

Dash sitting in grass with patriotic hat

Government Per Diem - Uncle Sam Special

Enjoy a special rate if you work for the US government