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Chicago, Illinois Holidays

The third biggest city in the US by population, Chicago gives New York a run for its money with a breath-taking skyline hugging the shores of Lake Michigan. Chicago has a pulsating music scene and a fine collection of eateries.
Chicago is a gateway city for some of America’s great journeys, Route 66 starts here, or board the California Zephyr Train bound for San Francisco, alternatively head South towards the Mississippi and the delights of Memphis and New Orleans.

This cosmopolitan playground is bursting with things to do. Sightseeing options range from Chicago icons like Millennium Park’s sculptures, fountains, gardens and event spaces to awe-inspiring architecture by Frank Lloyd Wright, Frank Gehry, Daniel Burnham and Louis Sullivan. Get above it all on The Ledge, a glass platform on the Skydeck at Willis Tower. 

Take in the beautiful cityscape with a stroll along the Chicago Riverwalk, where you can enjoy a waterside meal, Chicago’s culinary scene is filled with star chefs, ethnic eateries and award-winning fine dining, including 25 Michelin-starred eateries. Just as famous are the casual classics like Chicago-style hot dogs and deep-dish pizza.

Chicago is renowned for its cultural offerings with more than 60 museums and a dedicated Museum Campus, home to The Field Museum, Shedd Aquarium and Adler Planetarium. Don't miss the Art Institute of Chicago, containing 300,000 works in its permanent collection, and Museum of Science and Industry, the largest in the Western Hemisphere.

Chicago Tourist Attractions –

• Millennium Park

• Willis Tower

• Navy Pier

• Cloud Gate

• The Art Institute of Chicago

Our team of experts is on hand to help tailor-make your Canada holiday

Canada Expert GillianGillian
Canada Expert JenniferJennifer
Canada Expert JulieJulie

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We don't just know Canada, we love it!


Tailor Made for You

  • We tailor make every holiday made around you.
  • Tell us what you'd like to see, what type of accommodation you prefer and how you'd like to travel.
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Expert Advice

  • We don't just know Canada, we love it!
  • Our Canada Experts have travelled throughout Canada. They'll answer your questions with facts not guesses.
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