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Best 2 week Tours from Chicago

Find the best 2 week tours and trips starting from Chicago. Choose from 4 tours - we've found the most popular time to visit is in June with the most number of tour departures.

6 trips from Chicago with reviews

  • The Sumptuous Soul of America - 2020

    "The Luxury Gold Sumptuous Soul of America was without any hesitation the holiday..."
    destinations
    Chicago, St Louis, Louisville, Nashville, Memphis, Natchez, Frogmore, New Orleans
    age range
    5 to 99 year olds
    Country Region
    Southern USA
    Travel style
    Adventure, Group, Fully Guided+1 more
    operator
    Luxury Gold
    Book With Flexibility. If your plans change, choose a new date or tour with the same tour operator.
    If you change your travel plans after you book, convert what you paid to credit. Apply your credit to future tours run by the same tour operator.
    -10%
    Tour length
    14 days
    Price per day
    $421
    From
    $6,550
    US$5,895
    You save: $655
    Book With Flexibility. If your plans change, choose a new date or tour with the same tour operator.
    View tour
    More information
  • US & Canada Discovery

    destinations
    Chicago, Berlin, Toronto, Niagara Falls, Ottawa, Montreal, Stowe, New York City
    age range
    15 to 99 year olds
    Travel style
    Coach / Bus, In-depth Cultural+1 more
    operator
    Intrepid Travel
    Book With Flexibility. If your plans change, choose a new date or tour with the same tour operator.
    If you change your travel plans after you book, convert what you paid to credit. Apply your credit to future tours run by the same tour operator.
    Tour length
    11 days
    Price per day
    $367
    From
    US$4,040
    Book With Flexibility. If your plans change, choose a new date or tour with the same tour operator.
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    More information
  • US & Canada Discovery Winter

    destinations
    Chicago, Berlin, Niagara Falls, Toronto, Ottawa, Montreal, Stowe, Boston, New York City+1 more
    age range
    15 to 99 year olds
    Travel style
    Adventure, Christmas & New Year+1 more
    operator
    Intrepid Travel
    Book With Flexibility. If your plans change, choose a new date or tour with the same tour operator.
    If you change your travel plans after you book, convert what you paid to credit. Apply your credit to future tours run by the same tour operator.
    Tour length
    11 days
    Price per day
    $329
    From
    US$3,620
    Book With Flexibility. If your plans change, choose a new date or tour with the same tour operator.
    View tour
    More information
  • BBQ & Blues (ex Chicago) 2020

    destinations
    Chicago, Nashville, Memphis, New Orleans
    age range
    18 to 39 year olds
    Country Region
    Eastern USA, Southern USA, Southeast USA, Sun Belt+2 more
    Travel style
    Group, Fully Guided, Coach / Bus, Sightseeing+2 more
    operator
    Topdeck
    Book With Flexibility. If your plans change, choose a new date or tour with the same tour operator.
    If you change your travel plans after you book, convert what you paid to credit. Apply your credit to future tours run by the same tour operator.
    Tour length
    11 days
    Price per day
    $226
    From
    US$2,489
    Book With Flexibility. If your plans change, choose a new date or tour with the same tour operator.
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    More information
  • Historic Route 66

    "Our tour was enjoyable because of the mix of nostalgic sights & classic locations..."
    destinations
    Chicago, Springfield, St Louis, Branson, Oklahoma City, Amarillo, Albuquerque, Gallup, Grand Canyon National Park, Las Vegas, Los Angeles+4 more
    age range
    16 to 99 year olds
    Country Region
    Route 66
    Travel style
    Group, Partially Guided
    operator
    Grand American Adventures
    Tour length
    14 days
    Price per day
    $389
    From
    US$5,449
    View tour
    More information
  • Historic Route 66

    destinations
    Chicago, Pontiac, Springfield, St Louis, Branson, Oklahoma City, Amarillo, Albuquerque, Gallup, Grand Canyon, Las Vegas, Los Angeles+5 more
    age range
    16 to 99 year olds
    Travel style
    Adventure, Group, Fully Guided+1 more
    operator
    Exodus Travels
    Tour length
    14 days
    Price per day
    $389
    From
    US$5,449
    View tour
    More information

Best 2 week Tours from Chicago Reviews

  • "The Luxury Gold Sumptuous Soul of America was without any hesitation the holiday..."
    The Sumptuous Soul of America - 2020
  • "Our tour was enjoyable because of the mix of nostalgic sights & classic locations..."
    Historic Route 66