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From the harrowing tales of gangster life in the 1920s to the maritime majesty of riverboat cruises; Jumpstreet will take you on a deep dish journey through the highs, the lows and everything in-between that makes Chicago one of the most exciting cities in North America!

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Sample itinerary for Chicago trips


  • An orientation walk through the Loop to see Union Station, City Hall, the Civic Opera House, the Berlin Wall Monument, the Chicago Theatre;
  • Free time to discover the sights and smells of the Chicago French Market;
  • See how windy it actually is atop the second highest skyscraper in the U.S., the Willis Tower;


  • Investigate characters like Al Capone, The Untouchables, The Chicago Mob with a one-of-a-kind step-on guide;
  • Admire the famous Buckingham Fountain during a stroll in Grant Park;
  • Photo-op session in Millenium Park as you walk through the Jay Pritzker Pavilion and from the Crown Fountain to the famous Cloud Gate;
  • Get inspired by the works of Seurat, Van Gogh, Wood and Monet at the Art Institute of Chicago;
  • Find out if you're the next famous comedian to come out of Chicago during an Improv workshop;


  • Come face to face with beluga whales and sea otters at the Shedd Aquarium;
  • Find out why they say "the sky's the limit" as you become a space explorer at the Adler Planetarium;
  • Enjoy some free time to explore the Navy Pier on Chicago Harbor, where the entertainment and fun never stops;
  • Go support the Cubs at tonight's baseball game at Wrigley Field;


  • Immerse yourself in the history and future of engineering, medicine, science and technology at the Museum of Science and Industry;
  • Learn about Chicago's internationally-renowned architecture as you cruise along the Chicago River out to Lake Michigan;
  • Free time to explore and shop along Chicago's Magnificent Mile;
  • Take in some fresh air and take off your shoes on a walk along North Avenue Beach;
Our destination recommendations 
4 TO 6 Day trip
Year-Round Travel
Group picture in front of the bean
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What's Included

Tour Leaders
Carbon Neutral
Global Support Network
On Call 24/7
JSET-Photo de groupe en voyage scolaire en France

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