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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_Exterior
USA_Illinois_Staypineapple, An Iconic Hotel, The Loop_Lobby
USA_Illinois_Staypineapple, An Iconic Hotel, The Loop_Dining
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
USA_Illinois_Staypineapple, An Iconic Hotel, The Loop_Twin Queen

Inspire

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.

View Extraordinary Inspiration
Grizzly Bears in The Great Bear Rainforest

Wildlife and Nature

The Wildlife of Vancouver Island, British Columbia

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Monument Valley

Destination Guides

Arizona’s Stunning National Parks

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Two mule deer bucks at Yosemite National Park in California.

Wildlife and Nature

Wildlife of California’s Yosemite National Park

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Santa Monica Place, a Macerich shopping centre and fashion outlet
Culture, Music, Sport and Festivals
Macerich Shopping Centers and Fashion Outlets Read more
Thor's hammer in Bryce Canyon National Park in Utah USA at sunrise.
Tales from the Road
Tales from the Road – Utah Read more
Kootenay Rockies

Meet Our Team

Real North America Travel Experts

Rob Holmes, Journeyscape Travel Expert
Rob Holmes - Travel Expert
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.

Stuart
Stuart Whittington - Head of Product

Stuart is the Head of Product at Journeyscape and our sister brand, Journey Latin America. He is passionate about new adventures, venturing off the beaten path, and firmly believes that travel, when planned well, can be a force for good for all people and places involved.

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.

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

Explore Journey Latin America