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.
Stay Longer and Save
Book 3 nights or more and save!
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.
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 pet and parking rates.
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!
THANK YOU FOR YOUR SERVICE MILITARY RATE
Special rates for active Military, Veterans and their families.
Government Per Diem - Uncle Sam Special
Enjoy a special rate if you work for the US government