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.
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!
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*
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.
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.
Bark and Park Package
Enjoy 50% off our pet fee and parking rate!
Auto Club Rate
Auto club member? Save now on a Staypineapple room.
Young at Heart
Are you an AARP member? Take advantage of exclusive savings now!
Government Per Diem - Uncle Sam Special
Enjoy a special rate if you work for the US government