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.

A Person Lying On A Bed

Stay Longer and Save

Book 3 nights or more and save!

A Dog Sitting On A Bed

PINEAPPLE PUP PLUS ONE PACKAGE

Bring your pup and we'll WAIVE our daily pet fee for your 2025 stay when you book during the month of February.

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 pet and parking rates.

Small dog driving toy car

Auto Club Rate

Auto club member? Save now on a Staypineapple room.

Group of people sitting on edge of swimming pool holding pineapples

Young at Heart

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

A Soldier Holding A Flag

THANK YOU FOR YOUR SERVICE MILITARY RATE

Special rates for active Military, Veterans and their families.

Dash sitting in grass with patriotic hat

Government Per Diem - Uncle Sam Special

Enjoy a special rate if you work for the US government