A Better Kind of Business Trip

Skip boring and beige. Staypineapple is where work travel actually works.

You’ve stayed in enough cookie-cutter business hotels to know what you’re not getting: personality, a decent meal, and a lobby you’d actually want to sit in. Staypineapple is the boutique alternative for travelers who’d rather wake up somewhere interesting than somewhere forgettable.

We’re located in the heart of the cities where business gets done — Midtown Manhattan, the Loop in Chicago, Union Square in San Francisco, and more. Our rooms are thoughtfully designed, our F&B is genuinely good, and our service is the kind that remembers your name.

Discounted Rates
Surfpineapple/High-Speed Wi-Fi
PATH Water Bottle
VIP Concessions

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WHY STAYPINEAPPLE?

Business travel doesn’t have to feel so business-as-usual. At Staypineapple, we make work trips easier with comfortable rooms, central locations, thoughtful amenities, and a refreshingly friendly experience from check-in to checkout. Whether you’re booking one frequent traveler or arranging preferred rates for your company, our team is here to make staying productive, comfortable, and just a little more fun.

WHERE WE ARE

Every Staypineapple property is located where you need to be — close to financial districts, convention centers, transit hubs, and the kinds of neighborhoods that make a city worth visiting in the first place. Whether you're heading to a client meeting, a trade show, or just need a reliable home base for the week, you’ll be in the right place.

Notable for conference and convention travelers: Staypineapple New York is just minutes from the Jacob K. Javits Convention Center, and Staypineapple Chicago sits in the heart of the Loop's financial district with a private on-site meeting room available for small groups.

EXPLORE LOCATIONS

A Better Kind of Business Trip

Skip boring and beige. Staypineapple is where work travel actually works.

WHY STAYPINEAPPLE?

WHERE WE ARE

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