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Home / Event Planning & Tour / Destinations / Chicago


Having the distinction of being one of the world’s ten most influential cities since the World’s Fair was held there in 1893, Chicago has all of the wonders of a big city with the feel of a Midwest town. World class museums, cuisine, culture, entertainment, sports, industry and education all call Chicago home. Chicagoans also boast that their city has a wonderful working class population and great ethnic neighborhoods and foods.


Located on the southwestern shore of Lake Michigan, the “Windy City” offers a wide array of options for visitors. The Adler Planetarium and Museum, the Museum of Contemporary Art, and the famed Field Museum are just a few of the great museums to see in town. Don’t forget to check out the Sears Tower, Navy pier, the Shedd Aquarium, and one of dozens of Chicago’s famous deep dish pizza parlors to get a taste of something you can truly only find in the “City that Works”


Catch a show at the Chicago Theater or a game at fabled Wrigley Field if you wish. The city’s steep history also lends itself to interesting attractions like Al Capone’s old haunts and the Tommy Gun Dinner Theatre. The city’s proximity to one of the greatest of the Great Lakes offers the ability to enjoy sightseeing boat rides and fabulous views of the extensive skyline.


There’s so much to do in Chicago that you will simply just have to come back for more!

Sample Itinerary

*This itinerary is an example from a local school. We will be more than happy to assist with your itinerary, but please note that we currently do not create itineraries for these tours.

Day 1

  • 1. Motor coach departs from school
  • 2. Stop for lunch at service plaza in Indiana
  • 3. Arrive in Chicago in afternoon
  • 4. Check into hotel
  • 5. Dinner and shopping at Navy Pier

Day 2

  • 1. Breakfast at the hotel
  • 2. Visit the Field Museum of Natural History
  • 3. Enjoy lunch at McDonald’s
  • 4. Head to the Shedd Aquarium
  • 5. Dinner at Medieval Times including Tournament

Day 3

  • 1. Breakfast at the hotel
  • 2. Visit the Museum of Science and Industry
  • 3. Watch IMAX film
  • 4. Eat lunch at nearby restaurant of choice
  • 5. Board bus for return to Cleveland area

Tour Highlights


  • Adler Planetarium and Museum
  • Field Museum
  • Museum of Contemporary Art
  • Chicago Children’s Museum
  • Museum of Science and Industry
  • Shedd Aquarium and Oceanarium
  • Millenium Park


  • The Blue Man Group
  • IMAXChicago Theatre
  • Ford Center for the Performing Arts Oriental Theatre
  • LaSalle Bank Theatre
  • Cadillac Place Theatre
  • Auditorium Theatre of Roosevelt University
  • Drury Lane Theatre Water Tower Place