Is parking available?

We have valet parking on-site for an additional $75 per night.

Yes, we aren't just pet-friendly... we are pet-obsessed! We happily welcome dogs without a weight restriction. A $29.95 daily pet fee applies. When you book our Pineapple Pup Package you'll save 50% on your daily pet fee - only available when you book directly on Staypineapple.com. Plus, since our hotels are located in the heart of the city, we know (and kind of expect) that you’ll be out exploring the sites and going on adventures. If some of these plans don’t include your furry friend, THAT’S OKAY! We just ask that you use our doggie door hangers to let us know whether your room can be cleaned.

When is check-in or check-out?

In consideration of all our guests, check-in is after 4:00 PM and check-out is at 12:00 PM.

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Staypineapple: Iconic Boutique Hotel in The Loop

Visit Property Site
Hotel

100-150 Rooms

•

1 Restaurant

•

1 W Washington St, Chicago, IL 60602, USA

About this Property

Chosen by Conde Nast Traveler as one of the best hotels in the world, Staypineapple Chicago is an intimate boutique hotel like no other. Housed in the landmark Reliance Building, now beautifully restored, Staypineapple Chicago provides an authentic, luxurious, and historic taste of the Windy City.

In the heart of the Chicago Loop, across from Millennium Park, and home of the Atwood Restaurant, Staypineapple is near Chicago's top destinations and attractions. See the Windy City with the perfect home base: Staypineapple, an Iconic Hotel, The Loop, Chicago

Why We Like It For Groups

From

$139/night

Book This hotel

Visit the property’s booking site to check availability and get more information on the property.

Visit Property Site

Amenities

WiFi

Location

Chicago, IL

1 W Washington St, Chicago, IL 60602, USA

About the neighborhood

The Loop is Chicago’s vibrant downtown—perfect for groups looking to explore together. You’re steps from iconic spots like Millennium Park, the Art Institute, and the Riverwalk. Grab deep-dish, hit a rooftop bar, or catch a show in the Theatre District. Walkable, central, and full of energy, the Loop makes it easy to plan an unforgettable group getaway.

Getting around

Staypineapple Chicago is located in the highly walkable Loop neighborhood, putting you just steps from top attractions, dining, and shopping. Public transportation is convenient, with multiple train lines and bus stops nearby, making it easy to explore other parts of the city without a car.

If you prefer driving, parking options are available nearby, and rideshare services are widely accessible. Plus, the hotel offers complimentary bike rentals to explore the city at your own pace.