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Chicago Tours & Trips

Find the right tour for you through Chicago. We’ve got 65 tours going to Chicago, starting from just 6 days in length, and the longest tour is 80 days. The most popular month to go is June, which has the most number of tour departures.

65 trips through Chicago with 49 reviews

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Chicago Tours & Trips Reviews

  • "This tour is just fantastic. Don’t miss it out! Starting in wonderful New York with a great guided tour we were introd..."
    New York, Chicago and Miami City Tour
  • "I absolutely loved this trip. It was a great way to learn and experience this country. I met a bunch of absolutely great..."
    Chicago to San Francisco Road Trip
  • "Loved this tour! Our 50th Weddong Ann. And a trip we had always dreamed of. We grew up in the 50-60's ! The group was mo..."
    Route 66 Summer
  • "Spectacular and smart way for discovering the state. Some destinations should be changed or deleted in order to have suf..."
    Best of the USA Tour–New York to New York
  • "Quite simply, the best decision I ever made! This was the trip of a lifetime and a dream come true. The most amazing six..."
    Grand Trek
  • "I had a great time ! We saw lots of things and had lots of fun !..."
    Northern Trail