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Best 2 week Tours from Chicago

Best 2 week Tours from Chicago

Find the best 2 week tours and trips starting from Chicago. Choose from 8 tours - we've found the most popular time to visit is in October with the most number of tour departures.

Secure your getaway with a $99 DEPOSIT
ends on 31 Mar 2019
8 Trips from Chicago for 2 week
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8 Trips from Chicago for 2 week

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  • Northern Adventure

    "Isobel as our tour guide made my trip in NZ even better. Had a blast !"
    Instant Booking
    Just $99 deposit
    destinations
    Chicago, Madison, Sioux Falls, Mount Rushmore National Memorial, Cody, Yellowstone National Park, Jackson Hole, Salt Lake City, Kanab, Zion National Park, Las Vegas, Los Angeles+10 more
    starts/ ends in
    Chicago / Los Angeles
    age range
    18 to 35 year olds
    accommodation
    Hotel
    transport
    Train & Rail
    Travel style
    Coach / Bus
    operator
    Contiki
    Duration
    14 days
    Price per day
    $174
    From
    US$2,435
    Sign up to save $97
    22 May 2019
    7 spaces left
    5 Jun 2019
    8 spaces left
    View tour
    More information
  • The Sumptuous Soul of America (Summer 2019)

    "The Luxury Gold Sumptuous Soul of America was without any hesitation the holiday..."
    Instant Booking
    Just $99 deposit
    destinations
    Chicago, St Louis, Louisville, Nashville, Memphis, Natchez, Frogmore, New Orleans+6 more
    starts/ ends in
    Chicago / New Orleans
    age range
    5 to 99 year olds
    accommodation
    Hotel
    transport
    Coach / Bus
    Country Region
    Southern USA
    Travel style
    Adventure
    operator
    Luxury Gold
    -8%
    Duration
    14 days
    Price per day
    $420
    From
    $6,375
    US$5,874
    You save $500
    26 May 2019
    10 spaces left
    8 Sep 2019
    10+ spaces left
    View tour
    More information
  • The Blues Highway from Chicago to New Orleans Summer 2019

    11 day discovery tour through Chicago, Louisville, Nashville and 4 other destinations in USA

    Instant Booking
    Just $99 deposit
    destinations
    Chicago, Louisville, Nashville, Memphis, Clarksdale, Indianola, New Orleans+5 more
    starts/ ends in
    Chicago / New Orleans
    age range
    5 to 80 year olds
    accommodation
    Hotel
    transport
    Coach / Bus
    Country Region
    Eastern USA, Southern USA, Southeast USA, Sun Belt+2 more
    Travel style
    Coach / Bus
    operator
    Costsaver
    Duration
    11 days
    Price per day
    $160
    From
    US$1,765
    You save $55
    4 May 2019
    8 spaces left
    25 May 2019
    9 spaces left
    View tour
    More information
  • USA Travel Guide
    USA Travel Guide

    Prepare for an adventure in this stunning destination with our travel guide.

  • Historic Route 66

    "Our tour was enjoyable because of the mix of nostalgic sights & classic locations..."
    Just $99 deposit
    destinations
    Chicago, Springfield, St Louis, Branson, Oklahoma City, Amarillo, Santa Fe, Gallup, Grand Canyon National Park, Las Vegas, Los Angeles+9 more
    starts/ ends in
    Chicago / Los Angeles
    age range
    16 to 99 year olds
    accommodation
    Hotel
    transport
    Private Vehicle
    Country Region
    Route 66
    operator
    Grand American Adventures
    Duration
    14 days
    Price per day
    $240
    From
    US$3,355
    You save $104
    29 Jun 2019
    5 spaces left
    17 Aug 2019
    8 spaces left
    View tour
    More information
  • US & Canada Discovery

    12 day adventure tour through Chicago, Berlin, Niagara Falls and 5 other destinations in 2 different countries

    Instant Booking
    Just $99 deposit
    destinations
    Chicago, Berlin, Niagara Falls, Toronto, Montreal, Boston, Provincetown, New York City+6 more
    starts/ ends in
    Chicago / New York City
    age range
    15 to 99 year olds
    accommodation
    Hotel
    transport
    Private Vehicle
    Travel style
    Coach / Bus, In-depth Cultural+1 more
    operator
    Intrepid Travel
    Duration
    12 days
    Price per day
    $348
    From
    US$4,178
    You save $107
    13 May 2019
    10 spaces left
    22 Jul 2019
    8 spaces left
    View tour
    More information
  • US & Canada Discovery Winter

    12 day discovery tour through Chicago, Berlin, Niagara Falls and 6 other destinations in 2 different countries

    Instant Booking
    Just $99 deposit
    destinations
    Chicago, Berlin, Niagara Falls, Toronto, Ottawa, Montreal, Stowe, Boston, New York City+7 more
    starts/ ends in
    Chicago / New York City
    age range
    15 to 99 year olds
    accommodation
    Hotel
    transport
    Private Vehicle
    Travel style
    Adventure, Christmas & New Year+1 more
    operator
    Intrepid Travel
    Duration
    12 days
    Price per day
    $332
    From
    US$3,988
    You save $102
    4 Nov 2019
    10 spaces left
    16 Dec 2019
    10 spaces left
    View tour
    More information
  • BBQ & Blues (ex Chicago) 2019

    11 day in-depth cultural tour through Chicago, Nashville, Memphis, New Orleans in USA

    Instant Booking
    Just $99 deposit
    destinations
    Chicago, Nashville, Memphis, New Orleans+2 more
    starts/ ends in
    Chicago / New Orleans
    age range
    18 to 39 year olds
    accommodation
    Hotel
    transport
    Coach / Bus
    Country Region
    Eastern USA, Southern USA, Southeast USA, Sun Belt+2 more
    Travel style
    Coach / Bus, Sightseeing
    operator
    Topdeck
    Duration
    11 days
    Price per day
    $197
    From
    US$2,169
    Sign up to save $87
    5 Aug 2019
    10+ spaces left
    18 Oct 2019
    10+ spaces left
    View tour
    More information
  • BBQ and Blues (ex New Orleans) 2019

    11 day in-depth cultural tour through Chicago, Nashville, Memphis, New Orleans in USA

    Instant Booking
    Just $99 deposit
    destinations
    Chicago, Nashville, Memphis, New Orleans+2 more
    starts/ ends in
    Chicago / New Orleans
    age range
    18 to 39 year olds
    accommodation
    Hotel
    transport
    Coach / Bus
    Country Region
    Eastern USA, Southern USA, Southeast USA, Sun Belt+2 more
    Travel style
    Coach / Bus, Sightseeing
    operator
    Topdeck
    Duration
    11 days
    Price per day
    $197
    From
    US$2,169
    Sign up to save $87
    26 Jul 2019
    10+ spaces left
    8 Oct 2019
    10+ spaces left
    View tour
    More information

Best 2 week Tours from Chicago Reviews

  • "Isobel as our tour guide made my trip in NZ even better. Had a blast !"
    Northern Adventure
  • "The Luxury Gold Sumptuous Soul of America was without any hesitation the holiday..."
    The Sumptuous Soul of America (Summer 2019)
  • "Our tour was enjoyable because of the mix of nostalgic sights & classic locations..."
    Historic Route 66