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Show off your pet’s spooky, silly or adorable costume and win tail-wagging prizes in Dash, The Pineapple Pup’s 9th Annual Costume Contest!
Show off your pet’s spooky, silly or adorable costume and win tail-wagging prizes in Dash, The Pineapple Pup’s 9th Annual Costume Contest!
Staypineapple's own Dash, The Pineapple Pup has sniffed out the best pet-friendly parks near our hotels where you and your furry sidekick can stroll, sprint or simply wander.
We’re extending wellness beyond our human guests to our furry friends, helping them feel calm, safe and cared for during every stay.
Staypineapple Chicago was named one of the Best Boutique Hotels in the nation for a second year in a row!
Samantha and her family took Dash – Staypineapple’s lovable husky mascot – on an unforgettable Alaskan adventure after adopting him during their stay at The Maxwell Hotel.
Let the festivities begin! From music and food to art and culture, we’ve rounded up the best festivals happening near our locations throughout the year.
From iconic sights to historic gems, these are spots worth checking out near our locations
Staypineapple hotels are on top once again — amazing guest reviews say it all!
Catch all Storm games and enjoy special Friday night watch parties and events throughout the 2025 season
Check out all the Pride celebrations in each Staypineapple city and start planning your trip!
Read how we’re raising the bar on greener stays