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Chicago Destinations

Smart Student Travel

Historic and modern Chicago Tour

Chicago Illinois Landmarks

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Chicago Student Trip Details

3-5 days

Trip Duration


Intensity level 1-10




Meals Included


Parents Allowed

Historic and modern Chicago Tour

This is the perfect opportunity for your students to explore one of America’s most historic cities. They will be able to see some incredible architecture, including buildings from before World War II when it was still a thriving industrial hub! There are plenty of opportunities here that offer Midwestern hospitality in terms of scenery and food – try out those deep-dish pizzas while you’re at it!

Departure/ Return Location:

From your school or local airport if flying

Trip cost starting at:



All Meals, Premium Hotel Accommodations, Private Hotel Security, Expert Tour Guides, Round Trip Motor Coach Transportation and/or Airfare, Admissions to Popular Attractions, Gratuity, Taxes & Fees, Teachers travel Free

Not Included:

Travel insurance, Spending $$ for souvenirs

Hotel Stay:

Premium Hotel chains across the area

Other important Information

  • It’s helpful to keep a map of the city on hand.
  • Be prepared for temperature changes, as Lake Michigan borders Chicago’s eastern side.
  • The city offers various cuisines, including deep-dish pizza and 22 Michelin-star restaurants.
  • A common misconception about Chicago is that it’s always cold; however, the average high temperature in July is 82F degrees.
  • We can customize tours to fit your learning needs or themes such as STEM, Civil Rights, Leadership, Finance, Music & Band, College Bound, or simply by subject areas to fit your curriculum.
  • Optional Excursion Trip: Springfield, IL

Sample Itinerary


  • Fly or drive by motor coach
    • The Chicago Train System is one of the most extensive in America, with over 1500 miles. This means you can get anywhere within the city quickly and easily! And since all train lines meet downtown to form a loop (hence why they’re called “downtown loops”) it makes navigating very easy for visitors or newcomers alike who might not know where everything goes off until now: The place has got transportation covered.
  • Check into hotel
    • Typical Check-in time is between 3-4 pm CST.
  • Meet with your expert tour director
  • Willis Tower skydeck
    • The best time to visit is just after opening or after sunset. For great sunsets and twinkling nightscape viewing, plan on arriving at the Skydeck 30-45 minutes before your sunset time! Go to SunriseSunset for the Chicago sunset calendar. A picture to remember.
  • Lunch
  • Field Museum of Natural History
    • We recommend reserving at least four hours to ensure you hit the highlights. Visitors that arrive early usually enjoy a better experience. They can explore in the morning, gauge energy levels over lunch, then move to another Museum Campus attraction or enjoy the rest of the day at the Field.
  • Navy Pier
    • The pier has been a place of entertainment for years. From fishing to sunbathing, it’s not uncommon that people will find themselves enjoying this beautiful landmark in Chicago!
  • Dinner
  • Return to hotel


  • Breakfast at hotel
  • Shedd Aquarium
  • Spirit Of Chicago DJ Dance Cruise & Lunch Buffet
  • Museum of Science and Industry
  • “Magnificent Mile” shopping
  • Medieval Times tournament & dinner
  • Hotel check-in


  • Breakfast at hotel
  • Lincoln Park Zoo
  • Lunch
  • Blue Man Group Show
  • Depart


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