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.
UNLOCK EXCLUSIVE RATES
Join The CORE to unlock instant savings, exclusive offers, and special packages and promotions! You know you want in (and we want you too).
CHICAGO THANKSGIVING PARADE PACKAGE
Plan the perfect holiday escape with a spectacular view of the Chicago Thanksgiving Parade + popcorn and hot chocolate from your room!
4th Night Free
Stay for 4 nights, but pay for only 3 — meaning the 4th night is free!
IL Resident Staycation
Hey Illinois locals! Treat yourself to a staycay and get 20% off! Your couch won’t miss you, we promise.
PINEAPPLE PUP PACKAGE
Who let the dogs in?! You did, and we love it. Bring your pup to Chicago and get 50% off our pet fee plus a few pup-approved perks!
Road Trip Parking Package
Hitting the road this summer? Stay 2 nights or more and get a daily $40 parking credit for our on-site valet parking!
Pride 2025
In celebration of Pride, get 15% off when you book your stay with us in June through August!
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