Jennifer and her family’s cross-country journey led to unforgettable memories at Staypineapple Chicago — so special, they came back for more.
Read MoreTwo moms and their daughters shared a special first road trip from Vancouver, staying at The Maxwell Hotel and enjoying a Lauren Daigle concert in Seattle.
Read MoreAustin and his partner had a festive holiday experience at Staypineapple Chicago, watching the Thanksgiving Parade before exploring the nearby Christkindlmarket.
Read MoreBook the Pineapple Pup Plus One Package for waived pet fees!
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