StayPineapple, The Loop Chicago

A boutique gem in the heart of Chicago's bustling downtown, where vibrant design meets exceptional hospitality.

Located in The Loop neighbourhood near the theatres and Millennium Park, StayPineapple Chicago is a kaleidoscope of colours and textures, starting with the cheerful pineapple motifs adorning its façade to its eclectic furnishings within.

The lobby, adorned with plush velvet sofas and contemporary art pieces, invites you to unwind in style after a day of exploring. The rooms are equally enchanting, featuring bold patterns, vibrant hues and amenities including Naked Experience bedding, TV, fridge, WiFi and private bathroom

In true StayPineapple form, you'll find complimentary pineapple treats on a daily basis here: try the hotel's signature pineapple cupcakes and coffee. Stay active in the fitness centre, and take in panoramic views of the city skyline while sipping cocktails at the hotel's rooftop bar.

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Specialists in travel to North America

From Tailor Made holidays to pre-designed Private Journeys our Travel Experts will take you to the heart of North America.

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USA_Illinois_Staypineapple, An Iconic Hotel, The Loop_Lobby
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USA_Illinois_Staypineapple, An Iconic Hotel, The Loop_Guest Room
USA_Illinois_Staypineapple, An Iconic Hotel, The Loop_Suite
USA_Illinois_Staypineapple, An Iconic Hotel, The Loop_Bathroom
USA_Illinois_Staypineapple, An Iconic Hotel, The Loop_Guestroom
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Your edit for North America inspiration

Inspired by the landscapes, culture, wildlife and cuisine of Canada and the USA, explore our entertaining range of articles, travel tips, destination guides, recipes and much more.

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Meet Our Team

Real North America Travel Experts

Dominique
Dominique Kotsias - Product Manager

Dominique caught the North America travel bug when she was in her late teens and has travelled extensively throughout the USA and Canada, particularly drawn to the countries' outstanding natural beauty and wildlife. With over 10 years of product and marketing experience in North America, Dominique’s passion for the destination is infectious.

Mallika
Mallika Jain - Travel Expert

Mallika’s love for North America first began when she attended an American boarding school as a teenager. Her mother’s side of the family lived in the USA, so she enjoyed frequent trips across many states.

Me-NYC
Joshua Salter - Travel Expert

Joshua has been travelling to the USA since childhood, visiting his father and four siblings on the west coast. He is fortunate to have travelled to 42 of the 50 US states, and hopes to complete the set by his next big birthday.

Ben Line
Ben Line - Head of Sales

Ben Line is the Head of Sales at Journeyscape and our sister brand Journey Latin America, having lived abroad and travelled extensively over the years.

Why Journeyscape?

We love north america

  • Up-to-the-minute knowledge underpinned by 40 years experience
  • All of our Travel Experts have personal knowledge of the destination
  • A passion for the region runs through all we do

Travel with Confidence

  • Fully bonded and licensed
  • ATOL-protected
  • Book with confidence, knowing every penny is secure
  • 24 hour help available at every step of your journey

The Real North America

  • Our insider knowledge helps you go beyond the guidebooks
  • We hand-pick hotels both for their character and services
  • We'll give you authentic experiences based on your personal preferences

Journeyscape brought to you from the award-winning experts at Journey Latin America