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Chicago School Trip

If you’re ready to shake up the usual school trip itinerary, consider Chicago- recently named one of the Student Youth Travel Association’s Top Ten Student Destinations in the U.S.

Navy Pier

From the moment you hop off the El, Chicago’s vibrant energy draws you in to explore all her nooks and crannies.  Start on the shoreline of Lake Michigan at Navy Pier, a 50-acre playground packed with fun.  Get a bird’s eye view of the lake and the city as you soar 200 feet in the air on the Centennial Wheel.   Then splash down with an incredible tour of the lake or the Chicago River on a cruise departing from the pier.

Millennium Park and Magnificent Mile

Once the group is back on land, continue exploring at Millennium Park, boasting a state-of-the-art collection of architecture, landscape design and art (all free!) and a fresh spin on the “town square.”  So much fun!  Stroll down Chicago’s renowned Magnificent Mile for some upscale retail therapy or a slice of that famous deep-dish pizza.


Thrill-seekers will rejoice with a visit to the Skydeck Chicago in Willis Tower. They’ll step outside the tallest building in the Western Hemisphere at a height of 1,353 feet and onto the Ledge’s glass boxes, which extend 4.3 feet out from the Skydeck. Oh my.  As more of a low-altitude girl, I prefer to enjoy this attraction from street-level!

Museum of Science and Industry

The Museum of Science and Industry is another extraordinary attraction unique to Chicago. Open since 1933, MSI is one of the largest science museums in the world and dedicated to bringing science to life for children of all ages.

Blue Man Group

When the kids are ready to get their fun on, a Blue Man Group show is a must.  Wide eyes, blue bodies, paint and percussion are at the core of this unique performance.  The silent humor is infectious, the drumming loud and the toilet paper abundant; a perfect recipe for entertaining teenagers.

Great Escape Room®

The Great Escape Room® Chicago is another awesome way to spend an hour as your group works together to solve puzzles and scavenge for items necessary to escape the room.  You can choose the level of difficulty and the experience, ensuring that all have an amazing time.  Once successfully liberated, it’s just a few steps to a Chicago staple, Stan’s Donuts and Coffee.  Yum! Whether it’s January, December, or any month in between, Chicago is a phenomenal destination for students.  My naïve twenty-something self just didn’t recognize the distinct style and flair of Chicago prior to that first visit.  The slightly older and much wiser version knows a good thing when she visits – and so will your student group!


Our itineraries are just a starting point for your adventure.  We work directly with you to create a student trip that’s perfect for your group.  If you want a unique performance or learning experience, we make it happen. Do you need to change days or add an attraction?

Day 1:    

  • Arrive in Chicago and meet your “full-scope” tour director
  • Lincoln Park Zoo
  • Willis Tower Skydeck (tallest building in the Western Hemisphere)
  • 360 Chicago
  • Magnificent Mile
  • Blue Man Group or Comedy Sportz


Day 2:     

  • Shedd Aquarium
  • Performance or clinic at the Field Museum
  • Chicago Architecture Foundation River Cruise
  • Navy Pier


Day 3:     

  • Museum of Science and Industry with IMAX
  • Michigan Avenue
  • Depart for home

Contact For Custom Itinerary

I have been traveling with Kaleidoscope for 19 years and still continue to be impressed by their expertise and willingness to go the extra mile to make my trip a success!

Christy Hauert

Our trip was a great success! Everything was well throughout and organized. I am very pleased with the level of care that went in to our trip becoming a success. Thank you!

Darcie Bishop

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