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Chicago Fact: Navy Pier extends 2/3 of a mile into Lake Michigan and still rests on its original foundation of 20,000 Oregon timbers.

Chicago Highlights Group Tour

See historic landmarks, the hottest attractions and classic movie locations as Chicago Trolley & Double Decker Co. takes you and your group on your very own private viewing of our Signature Tour. Request a quote on-line or call our charter sales dept. at 773-648-5000 to book today!

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Tour Details

Tour Length: 2 Hours
Group Size: 32 Person Max on Trolleys / 70 Person Max on Double Deckers


Whether you're a first-time visitor to Chicago or lifelong resident, the Highlights tour is the perfect way to see the Windy City. This entertaining and informative two-hour tour passes by Chicago's historic landmarks, classic movie locations, and hottest attractions including:

  • Millennium Park: Cloud Gate (The Bean), the Park Shop
  • Michigan Avenue Bridge: Trump Tower, Wrigley Building, boat tours
  • Block Thirty Seven: State Street shopping, Picasso, Garrett Popcorn Shop, Chicago Theatre, Macy's 
  • Art Institute: Grant Park, Millennium Park, Orchestra Hall
  • Hilton Towers and Hotel: Buckingham Fountain
  • Field Museum of Natural History: Shedd Aquarium, Adler Planetarium, Soldier Field
  • Sheraton Chicago: NBC Tower, AMC Theater, Riverwalk
  • Navy Pier: Shopping, dining, boat tours, family attractions, and more
  • The Magnificent Mile: Wrigley Building, Tribune Tower, Nordstrom's, Apple Store, Nike Town
  • Hancock Center: Hancock Observatory and Signature Room, Bloomingdale's, Cheesecake Factory, Oak Street shopping
  • Water Tower: American Girl Place, Water Tower Place shopping, Chicago Visitor Center, Lookingglass Theatre, Mag Mile shopping
  • River North: Hard Rock Cafe, Rainforest Cafe, Ed Debevic's, Portillo's, Retro McDonald's, Pizzeria Uno,
  • Willis (formerly Sears) Tower: The Skydeck, Board of Trade, Union Station  

See all of it or just a part of it. Customize your group tour to hit all the highlights that your group wants to see. If there is an area of the city you'd like to see or subject of interest that you would like to learn about, let us know and we will add it to the tour. Use a trolley to make it an extra special Chicago experience or if you have a larger sized group it is always fun to sit on top of one of our Double Deckers.


For more information, call our Group Sales Department at 773-648-5000 and ask to speak with a Group Sales representative or request a quote on-line.

Request a Quote