Special Offers & Packages | Staypineapple Chicago
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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 personalized hospitality, ultra comfy beds, and the signature amenities you’ve come to love from a Staypineapple hotel.
If you’re wondering where to stay in Chicago, our hotel in The Loop puts you right in the heart of the city’s best dining, shopping, and attractions — all wrapped in the unique Staypineapple charm.
Your next great Chicago adventure awaits. Start packing.
The More You Stay, The Less You Pay
Get 50% off your 3rd night or 4th night free
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).
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.
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!
Park and Bark Package
Enjoy 50% off pet and parking rates.
Pride 2026
In celebration of Pride, get 15% off when you book your stay with us in June through August!
IL Resident Staycation
Hey Illinois locals! Treat yourself to a staycay and get 20% off! Your couch won’t miss you, we promise.
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