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Chicago Tours & Trips

Chicago Tours & Trips

Find the right tour for you through Chicago. We've got 48 tours going to Chicago, starting from just 7 days in length, and the longest tour is 75 days. The most popular month to go is June, which has the most number of tour departures.

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48 Chicago holiday packages with 70 reviews

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  • Mackinac Island & the Great Lakes

    8 day discovery tour through Detroit, Frankenmuth, Mackinac Island and 6 other destinations in USA

    Flexible payments
    destinations
    Detroit, Frankenmuth, Mackinac Island, Tunnel of Trees, Charlevoix, Petoskey, Sleeping Bear Dunes National Lakeshore, Grand Rapids, Chicago+7 more
    starts/ ends in
    Detroit / Chicago
    age range
    8 to 80 year olds
    accommodation
    Hotel, Lodge
    transport
    Coach / Bus
    Regions
    Eastern USA, Midwest USA, Great Lakes+1 more
    Travel style
    Coach / Bus
    operator
    Globus
    -8%
    Duration
    8 days
    Price per day
    $303
    From
    $2,619
    US$2,422
    You save: $197
    7 Jun 2020
    8 spaces left
    14 Jun 2020
    7 spaces left
    View tour
    More information
  • Eastern Cities Plus

    8 day discovery tour through New Orleans, Memphis, Nashville and 3 other destinations in USA

    Flexible payments
    destinations
    New Orleans, Memphis, Nashville, Chicago, Cleveland, New York City+4 more
    starts/ ends in
    New Orleans / New York City
    age range
    18 to 38 year olds
    accommodation
    Hotel, Lodge
    transport
    Private Vehicle
    Country Region
    Eastern USA
    Travel style
    Adventure
    operator
    Trek America
    Duration
    8 days
    Price per day
    $223
    From
    US$1,786
    You save: $33
    1 May 2020
    10+ spaces left
    16 Oct 2020
    10+ spaces left
    View tour
    More information
  • Maples & Monuments

    9 day adventure tour through Toronto, Detroit, Chicago and 5 other destinations in 2 different countries

    Instant Booking
    Flexible payments
    destinations
    Toronto, Detroit, Chicago, Cleveland, Niagara Falls, Harrisburg, Washington DC, New York City+6 more
    starts/ ends in
    Toronto / New York City
    age range
    18 to 39 year olds
    accommodation
    Hostel, Hotel
    transport
    Coach / Bus
    Country Region
    Eastern USA
    Travel style
    Coach / Bus, In-depth Cultural+1 more
    operator
    Topdeck
    Duration
    9 days
    Price per day
    $177
    From
    US$1,589
    Sign up to save $32
    5 Jun 2020
    10+ spaces left
    3 Jul 2020
    10+ spaces left
    View tour
    More information
  • Best Time to Visit West Coast, USA (with California)
    Best Time to Visit West Coast, USA (with California)

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

  • Grand Northern (From April 2020)

    "This was my 5th contiki and again loved every minute of it. I have made some amazing..."
    Instant Booking
    Flexible payments
    destinations
    New York City, Boston, Quebec City, Montreal, Rockport, Toronto, Niagara Falls, Cleveland, Chicago, Milwaukee, Madison, Sioux Falls, Badlands National Park, Mount Rushmore National Memorial, Cody, Yellowstone National Park, Grand Teton National Park, Salt Lake City, Bryce Canyon National Park, Kanab, Grand Canyon National Park, Zion National Park, Las Vegas, Mojave Desert, Los Angeles+24 more
    starts/ ends in
    New York City / Los Angeles
    age range
    18 to 35 year olds
    accommodation
    Hotel
    transport
    Train & Rail
    Travel style
    Coach / Bus
    operator
    Contiki
    Duration
    25 days
    Price per day
    $161
    From
    US$4,025
    8 May 2020
    7 spaces left
    22 May 2020
    10+ spaces left
    View tour
    More information
  • New York to Los Angeles on Route 66

    "Our road trip adventure from New York to Los Angeles was the best trip I've ever..."
    Instant Booking
    Flexible payments
    destinations
    New York City, Chicago, Springfield, Tulsa, Albuquerque, Grand Canyon, Las Vegas, Los Angeles+7 more
    starts/ ends in
    New York City / Los Angeles
    age range
    18 to 99 year olds
    accommodation
    Hotel
    transport
    Jeep & 4WD, Private Vehicle, Plane+2 more
    Country Region
    Route 66
    Travel style
    Adventure
    operator
    Discovery Nomads
    Duration
    14 days
    Price per day
    $172
    From
    US$2,403
    You save: $44
    1 Apr 2020
    10 spaces left
    7 Apr 2020
    10 spaces left
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    More information
  • New York, Chicago and Miami City Tour

    "This tour is just fantastic. Don’t miss it out! Starting in wonderful New York..."
    Instant Booking
    Flexible payments
    destinations
    New York City, Chicago, Miami+2 more
    starts/ ends in
    New York City / Miami
    age range
    18 to 99 year olds
    accommodation
    Hotel
    transport
    Plane
    Country Region
    Eastern USA
    Travel style
    Discovery, Christmas & New Year+1 more
    operator
    Discovery Nomads
    Duration
    7 days
    Price per day
    $250
    From
    US$1,748
    You save: $32
    17 Dec 2019
    10 spaces left
    18 Dec 2019
    10 spaces left
    View tour
    More information
  • New York to Miami Adventure Tour

    10 day independent tour through New York City, Chicago, Washington DC, Miami in USA

    Instant Booking
    Flexible payments
    destinations
    New York City, Chicago, Washington DC, Miami+3 more
    starts/ ends in
    New York City / Miami
    age range
    18 to 99 year olds
    accommodation
    Hotel
    transport
    Plane
    Country Region
    Eastern USA
    Travel style
    Discovery, Christmas & New Year+1 more
    operator
    Discovery Nomads
    Duration
    10 days
    Price per day
    $197
    From
    US$1,966
    You save: $36
    17 Dec 2019
    10 spaces left
    18 Dec 2019
    10 spaces left
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    More information
  • The Sumptuous Soul of America - Summer 2020

    "The Luxury Gold Sumptuous Soul of America was without any hesitation the holiday..."
    Instant Booking
    Flexible payments
    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
    -13%
    Duration
    14 days
    Price per day
    $411
    From
    $6,575
    US$5,748
    You save: $828
    24 May 2020
    10+ spaces left
    14 Jun 2020
    10 spaces left
    View tour
    More information
  • US & Canada Discovery

    11 day adventure tour through Chicago, Berlin, Toronto and 5 other destinations in 2 different countries

    Instant Booking
    Flexible payments
    destinations
    Chicago, Berlin, Toronto, Niagara Falls, Ottawa, Montreal, Stowe, 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
    11 days
    Price per day
    $354
    From
    US$3,895
    11 May 2020
    10+ spaces left
    20 Jul 2020
    10+ spaces left
    View tour
    More information
  • USA Crossing Ways (from New York City)

    19 day hop on/off tour through New York City, Philadelphia, Washington DC and 7 other destinations in USA

    Instant Booking
    Flexible payments
    destinations
    New York City, Philadelphia, Washington DC, Buffalo, Chicago, Denver, Salt Lake City, Las Vegas, Grand Canyon National Park, Los Angeles+9 more
    starts/ ends in
    New York City / Los Angeles
    age range
    10 to 99 year olds
    transport
    Bicycle, Private Vehicle
    Travel style
    Discovery, Christmas & New Year+1 more
    operator
    Bamba Experience
    Duration
    19 days
    Price per day
    $86
    From
    US$1,631
    You save: $30
    16 Dec 2019
    10 spaces left
    17 Dec 2019
    10 spaces left
    View tour
    More information
  • The Great 48

    75 day discovery tour through Miami, Key West, Savannah and 53 other destinations in USA

    Flexible payments
    destinations
    Miami, Key West, Savannah, Raleigh, Asheville, Great Smoky Mnts, Charleston, Washington DC, Delaware City, New York City, Rhode Island, Boston, Acadia National Park, White Mountains National Forest, Buffalo, Cleveland, Indianapolis, Nashville, Birmingham, New Orleans, Tupelo, Memphis, St Louis, Chicago, Minneapolis, Kansas City, Oklahoma City, Austin, San Antonio, Carlsbad Caverns National Park, Roswell, Santa Fe, Great Sand Dunes NP, Buena Vista, Boulder, Rocky Mountain National Park, Mount Rushmore National Memorial, Little Bighorn Battlefield National Monument, Yellowstone National Park, Craters of the Moon National Monument, Salt Lake City, Moab, Arches National Park, Dead Horse Point State Park, Monument Valley, Grand Canyon National Park, Las Vegas, Los Angeles, Santa Barbara, Monterey, Yosemite NP, San Francisco, Eureka, Redwood National Park, Portland, Seattle+54 more
    starts/ ends in
    Miami / Seattle
    age range
    18 to 38 year olds
    accommodation
    Hotel, Camping, Lodge
    transport
    Private Vehicle
    operator
    Trek America
    Duration
    75 days
    Price per day
    $153
    From
    US$11,488
    You save: $211
    3 Jun 2020
    9 spaces left
    View tour
    More information
  • Highlights of Route 66 with Mother Road & Albuquerque Balloon Fiesta

    16 day in-depth cultural tour through Chicago, Pontiac, Springfield and 14 other destinations in USA

    Flexible payments
    destinations
    Chicago, Pontiac, Springfield, St Louis, Branson, Oklahoma City, Amarillo, Tucumcari, Albuquerque, Gallup, Winslow, Williams, Grand Canyon National Park, Seligman, Las Vegas, Barstow, Los Angeles+15 more
    starts/ ends in
    Chicago / Los Angeles
    age range
    8 to 99 year olds
    accommodation
    Hotel, Guesthouse
    transport
    Coach / Bus
    Country Region
    Route 66
    Travel style
    Coach / Bus
    operator
    Cosmos
    Duration
    16 days
    Price per day
    $184
    From
    US$2,949
    24 Sep 2020
    8 spaces left
    View tour
    More information
  • Historic Route 66

    "Our tour was enjoyable because of the mix of nostalgic sights & classic locations..."
    Flexible payments
    destinations
    Chicago, Springfield, St Louis, Branson, Oklahoma City, Amarillo, Albuquerque, 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
    $262
    From
    US$3,670
    You save: $109
    27 Jun 2020
    3 spaces left
    29 Aug 2020
    10+ spaces left
    View tour
    More information
  • USA & Canada Adventure

    "Had a great time!! It was a great feeling to see new cities as well as getting know..."
    Instant Booking
    Flexible payments
    destinations
    New York City, Boston, Quebec City, Montreal, Toronto, Niagara Falls, Detroit, Chicago, Cleveland, Washington DC, Philadelphia+10 more
    starts/ ends in
    New York City / New York City
    age range
    18 to 39 year olds
    accommodation
    Hostel, Hotel
    transport
    Coach / Bus
    Travel style
    Coach / Bus
    operator
    Topdeck
    Duration
    14 days
    Price per day
    $170
    From
    US$2,379
    Sign up to save $48
    31 May 2020
    10+ spaces left
    28 Jun 2020
    10+ spaces left
    View tour
    More information
  • US & Canada Discovery Winter

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

    Instant Booking
    Flexible payments
    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
    -15%
    Duration
    11 days
    Price per day
    $280
    From
    $3,620
    US$3,077
    You save: $543
    16 Dec 2019
    6 spaces left
    6 Jan 2020
    6 spaces left
    View tour
    More information
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Chicago Holiday and Vacation Packages Reviews

  • "Covering a total distance of approx 6,045 km in 24 days there are some very long..."
    Grand Northern (From April 2020)
  • "Our road trip adventure from New York to Los Angeles was the best trip I've ever..."
    New York to Los Angeles on Route 66
  • "This tour is just fantastic. Don’t miss it out! Starting in wonderful New York..."
    New York, Chicago and Miami City Tour
  • "The Luxury Gold Sumptuous Soul of America was without any hesitation the holiday..."
    The Sumptuous Soul of America - Summer 2020
  • "Our tour was enjoyable because of the mix of nostalgic sights & classic locations..."
    Historic Route 66
  • "Had a great time!! It was a great feeling to see new cities as well as getting know..."
    USA & Canada Adventure