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Chicago Tours and Trips 2018/2019

Find the right tour for you through Chicago. We’ve got 78 tours going to Chicago, starting from just 6 days in length, and the longest tour is 75 days. The most popular month to go is August, which has the most number of tour departures.

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ends on 27 Jun 2018

78 trips through Chicago with 83 reviews

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Chicago Tours and Trips Reviews

  • "This tour is just fantastic. Don’t miss it out! Starting in wonderful New York..."
    New York, Chicago and Miami City Tour
  • "The trip Rockies, Yellowstone and Mt. Rushmore was amazing. Yellowstone was a dream...."
    Rockies, Yellowstone & Mt Rushmore
  • "Our road trip adventure from New York to Los Angeles was the best trip I've ever..."
    Road trip on Route 66: from New York to Los Angeles
  • "I absolutely loved this trip. It was a great way to learn and experience this country...."
    Chicago to San Francisco Road Trip
  • "Isobel as our tour guide made my trip in NZ even better. Had a blast !"
    Northern Adventure
  • "tour took us exactly where we wanted to go with someone else doing the organising!"
    Dixieland & Rhythms 2018