Chicago

America’s third largest city is famous for its bold skyline, fascinating museums and galleries, proud musical heritage and delicious food.

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Known as the Windy City, Chicago’s magnificent skyline dominates the south-west corner of Lake Michigan. The city’s grandeur is best viewed from above. Skydeck on the 103rd floor of the Willis Tower, formerly the Sears Tower, is the highest observation deck in the USA, or an alternative view is from 360 Chicago on the 94th floor of the John Hancock Center. Another great way to see the city is from the water on a boat cruise on Lake Michigan or along the Chicago River.

Chicago has some fantastic museums and galleries. The Art Institute of Chicago has the best Impressionist collection outside Paris, as well as many contemporary masterpieces. The nearby Field Museum is home of SUE, the largest and most complete T-Rex ever discovered.

The Cloud Gate sculpture, known as the Bean, is just one highlight of the public art among the fountains and gardens of 24-acre Millennium Park, while the 18-mile Lakefront Trail is one of the best walks in the city.

It’s fitting that Chicago is apparently named after the Algonquin word ‘shikaakwa’ for the onions that grew locally. The city is renowned for its food and drink – from Deep-Dish Pizza and Italian Beef Sandwiches to the breweries and cocktail bars. The Magnificent Mile of restaurants and shops through the heart of the city from the Chicago River to Oak Street is a good place to sample a wide range of local and international cuisine.

Chicago also has a rich musical heritage, particularly in jazz and blues, so catching live music is a must in the city – from Buddy Guy’s Legends to Green Mill Jazz Club, a former Al Capone haunt.

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Creating tailor-made Holidays for 40 years

Things to do in Chicago

Explore a wide range of activities, excursions and one-of-a-kind experiences in Chicago, tried and tested personally by our travel experts.

Places to Stay in Chicago

Browse our unrivalled portfolio of accommodation in Chicago. Every option has been carefully chosen by our team of travel experts.

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About Us

Brought to you by Journey Latin America, the team behind the UK's No.1 Specialist in travel to Central and South America, Journeyscape is a collection of inspiring, authentic and extraordinary journeys delivered with exceptional customer service across the USA and Canada.

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Holiday Styles

Centred around Canada and the USA's most unforgettable experiences and unique activities, our holiday styles cater to every interest.

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How we travel

Whether it's a tailor-made holiday created from scratch, or a pre-designed holiday crafted by our experts, we can provide an incredible holiday experience based on your specific preferences.

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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.

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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

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Thor's hammer in Bryce Canyon National Park in Utah USA at sunrise.

Tales from the Road

Tales from the Road – Utah

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Chesapeake Bay, Capital Region

Tales from the Road

Tales from the Road: The Capital Region

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Kootenay Rockies

Meet Our Team

Real North America Travel Experts

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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.

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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.

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

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  • A passion for the region runs through all we do

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The Real North America

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