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CHICAGO

JSED-Chicago-Banner3-min

STUDENT TOURS TO CHICAGO

Discover the stunning architecture, world-class museums, rich civil rights history, and vibrant communities that make Chicago one of North America's most exciting cities! 

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Sample itinerary for Chicago:

DAY 1 · DEPARTURE - CHICAGO
  • Departure from your school.
  • Arrive in Chicago and meet your Tour Director—it’s time to begin your trip!
  • Stretch your legs on an orientation walk through the Loop to see Union Station, City Hall, the Civic Opera House, the Berlin Wall Monument, and the Chicago Theatre.
  • Enjoy free time to discover the sights and smells of the Chicago French Market.
  • Head up to the Willis Tower Skydeck for panoramic views of the city and Lake Michigan from one of the tallest skyscrapers in the United States.
  • You can't visit Chicago without trying its most famous local delicacy—deep dish pizza!
  • Check in your group at the hotel before enjoying a good night’s sleep.
DAY 2 · CHICAGO
  • Have breakfast at the hotel and get ready for the day.
  • Step back into the Roaring Twenties during the Original Chicago Gangster Tour, where you'll learn about Al Capone and other Prohibition-era legends.
  • Admire the Buckingham Fountain during a stroll through Grant Park, then continue to Millennium Park to visit the Crown Fountain, the Jay Pritzker Pavilion, and of course, the iconic Cloud Gate (“The Bean”).
  • After some free time for lunch in the Loop, visit the Art Institute of Chicago, home to masterpieces by Van Gogh, Seurat, Wood, Monet, and many more.
  • Have dinner at a delicious local restaurant, and end your day with an Improv workshop, where you’ll learn the secrets of Chicago’s famous comedy scene.
  • Return to your hotel for a good night’s sleep.
DAY 3 · CHICAGO
  • Have breakfast at the hotel and get ready for the day.
  • Dive into Chicago’s natural wonders at the Shedd Aquarium, home to beluga whales, sea otters, and tropical fish in an impressive Beaux-Arts setting.
  • Explore the stars, planets, and the future of space travel at the Adler Planetarium.
  • Enjoy free time for lunch and exploration at the Navy Pier, Chicago’s lakeside playground packed with shops, restaurants, and attractions.
  • Take a Chicago Architecture Cruise along the river and out to Lake Michigan to admire the city’s world-famous skyline from the water.
  • Tonight, cheer on the Cubs at a baseball game at Wrigley Field—a classic Chicago experience! (Dinner on site.)
  • Return to your hotel for a good night’s sleep.
DAY 4 · CHICAGO - DEPARTURE
  • Have breakfast at the hotel and pack up your luggage for departure. 
  • Explore the innovative side of Chicago at the Museum of Science and Industry, where you’ll get hands-on with exhibits in engineering, medicine, and technology.
     
  • Enjoy some free time to explore and shop along the Magnificent Mile.
  • Take in the stunning views and vibrant atmosphere of the Windy City on a final stroll along the Chicago Riverwalk.
  • It’s already the end of your trip! Head back home and say goodbye to your tour director before reuniting with your families at school.
Our destination recommendations 
4 to 6 day trips
Year-Round
Sustainability

The transportation portion of your trip is carbon neutral when you travel by bus. Learn about our Choose Earth Carbon Offset Program.

Themes
Customize your itinerary around a chosen theme by adding sports or STEM-focused activities, art workshops, and theatre performances.
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JSED-Chicago-357x262

What's Included

JSET-Icon-Tour Leaders
All-Star
Tour Directors
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Carbon Neutral
Travel
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Global Support Network
On Call 24/7
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Trips to the USA

From history-filled routes to dynamic cities, the U.S. is packed with memorable, hands-on, and educational adventures your school will love to explore. Let us guide the way!

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Carbon Offset Matching Program

Jumpstreet and WorldStrides Canada have partnered with Carbonzero to provide our participants with carbon neutral travel experiences, and we will cover half the cost!

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Health & Safety on Tour

The health and safety of our participants is our top priority. Find out how Jumpstreet and its global support network can support you on your trip and give you the peace of mind you're looking for.

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