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Chicago Tours and Trips 2018/2019

Chicago Tours and Trips 2018/2019

Find the right tour for you through Chicago. We’ve got 54 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 June, which has the most number of tour departures.

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54 trips through Chicago with 60 reviews

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  • New York, Chicago and Miami City Tour

    "This tour is just fantastic. Don’t miss it out! Starting in wonderful New York..."
    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
    operator
    Discovery Nomads
    Days
    7
    Our saving
    $66
    From
    US $ 2,133
    days
    7
    $305 per day
    23 Oct 2018 10 spaces left
    24 Oct 2018 10 spaces left
    View MoreGetDownload Brochure
  • Splendour in the American Heartland (Summer 2019)

    8 day in-depth cultural tour through Chicago, St. Louis, Louisville, Nashville in USA

    destinations
    Chicago, St. Louis, Louisville, Nashville+2 more
    starts/ ends in
    Chicago / Nashville
    age range
    5 to 99 year olds
    accommodation
    Hotel
    transport
    Coach / Bus, Plane
    Travel style
    Coach / Bus
    operator
    Luxury Gold
    -13%
    Days
    8
    Our saving
    $464
    From
    $3,650
    US $ 3,186
    days
    8
    $398 per day
    12 May 2019 10 spaces left
    26 May 2019 10 spaces left
    View MoreGetDownload Brochure
  • Dixieland & Rhythms (from Chicago to New Orleans)

    "tour took us exactly where we wanted to go with someone else doing the organising!"
    destinations
    Chicago, St Louis, Nashville, Memphis, Hammond, Lafayette, New Orleans+5 more
    starts/ ends in
    Chicago / New Orleans
    age range
    8 to 99 year olds
    accommodation
    Hotel, Guesthouse
    transport
    Train & Rail, Coach / Bus
    Regions
    Southern USA, Sun Belt, Mississippi+1 more
    Travel style
    Coach / Bus
    operator
    Cosmos
    -3%
    Days
    11
    Our saving
    $50
    From
    $1,809
    US $ 1,759
    days
    11
    $160 per day
    1 Apr 2019 10+ spaces left
    8 Apr 2019 9 spaces left
    View MoreGetDownload Brochure
  • USA Travel Guide
    USA
    Travel Guide
    Prepare for an adventure in this stunning destination with our travel guide.
  • Big Apple to Chicago

    8 day discovery tour through New York City, Philadelphia, Washington DC and 4 other destinations in USA

    destinations
    New York City, Philadelphia, Washington DC, Great Smoky Mnts, Nashville, Louisville, Chicago+6 more
    starts/ ends in
    New York City / Chicago
    age range
    15 to 70 year olds
    accommodation
    Hotel, Camping
    transport
    Private Vehicle
    Country Region
    Eastern USA
    operator
    Intrepid Travel
    Days
    8
    Our saving
    $35
    From
    US $ 1,360
    days
    8
    $170 per day
    9 Jun 2019 10+ spaces left
    28 Jul 2019 10+ spaces left
    View MoreGetDownload Brochure
  • Rockies, Yellowstone & Mt Rushmore

    "The trip Rockies, Yellowstone and Mt. Rushmore was amazing. Yellowstone was a dream...."
    destinations
    Denver, Sinks Canyon State Park, Jackson, Yellowstone National Park, Devils Tower National Monument, Mount Rushmore National Memorial, Badlands National Park, Sioux Falls, Goose Island, Chicago+9 more
    starts/ ends in
    Denver / Chicago
    age range
    15 to 70 year olds
    accommodation
    Hotel, Camping
    transport
    Private Vehicle
    Travel style
    Adventure
    operator
    Intrepid Travel
    Days
    11
    Our saving
    $44
    From
    US $ 1,731
    days
    11
    $157 per day
    7 Jun 2019 10+ spaces left
    14 Jun 2019 10+ spaces left
    View MoreGetDownload Brochure
  • USA East Coast Road Trip Encompassed

    20 day discovery tour through New York City, Finger Lakes, Niagara Falls and 13 other destinations in USA

    destinations
    New York City, Finger Lakes, Niagara Falls, Detroit, Chicago, Louisville, Nashville, Memphis, New Orleans, Panama City, Orlando, St Augustine, Savannah, Charleston, Myrtle Beach, Washington DC+15 more
    starts/ ends in
    New York City / New York City
    age range
    12 to 70 year olds
    accommodation
    Hostel, Hotel, Camping
    transport
    Private Vehicle
    Country Region
    Eastern USA
    Travel style
    Sightseeing
    operator
    G Adventures
    Days
    20
    Our saving
    $177
    From
    US $ 3,549
    days
    20
    $177 per day
    9 Apr 2019 10+ spaces left
    14 Apr 2019 10+ spaces left
    View MoreGetDownload Brochure
  • New York to New Orleans Road Trip

    11 day discovery tour through New York City, Finger Lakes, Niagara Falls and 6 other destinations in USA

    destinations
    New York City, Finger Lakes, Niagara Falls, Detroit, Chicago, Louisville, Nashville, Memphis, New Orleans+8 more
    starts/ ends in
    New York City / New Orleans
    age range
    12 to 70 year olds
    accommodation
    Hostel, Camping
    transport
    Private Vehicle
    Country Region
    Eastern USA
    operator
    G Adventures
    Days
    11
    Our saving
    $100
    From
    US $ 1,999
    days
    11
    $182 per day
    9 Apr 2019 10+ spaces left
    14 Apr 2019 10+ spaces left
    View MoreGetDownload Brochure
  • Grand Trek

    "Quite simply, the best decision I ever made! This was the trip of a lifetime and..."
    destinations
    New York City, Niagara Falls, Chicago, Wisconsin Rapids, Badlands NP, Mt. Rushmore, Cody, Yellowstone, Jackson, Grand Teton National Park, Lake Tahoe, Yosemite NP, San Francisco, Monterey, Big Sur, Los Angeles, Las Vegas, Zion National Park, Lake Powell, Grand Canyon, Monument Valley, Roswell, Santa Fe, Carlsbad Caverns National Park, San Antonio, New Orleans, Birmingham, Appalachian Mountains, Washington DC, Philadelphia+29 more
    starts/ ends in
    New York City / New York City
    age range
    18 to 38 year olds
    accommodation
    Hostel, Hotel, Camping, Lodge+1 more
    transport
    Private Vehicle
    Country Region
    Route 66
    Travel style
    Adventure
    operator
    Trek America
    -18%
    Days
    42
    Our saving
    $982
    From
    $5,579
    US $ 4,597
    • +$430 local payments
    days
    42
    $109 per day
    27 Mar 2019 5 spaces left
    10 Apr 2019 10 spaces left
    View MoreGetDownload Brochure
  • Mackinac Island featuring The Grand Hotel and the Tulip Festival (Chicago, IL to Southfield, MI)

    8 day discovery tour through Chicago, Holland, Grand Rapids and 4 other destinations in USA

    destinations
    Chicago, Holland, Grand Rapids, Mackinac Island, Frankenmuth, Dearborn, Southfield+5 more
    starts/ ends in
    Chicago / Southfield
    age range
    5 to 99 year olds
    Regions
    Eastern USA, Midwest USA, Great Lakes+1 more
    Travel style
    Adventure
    operator
    Collette
    Days
    8
    Our saving
    $82
    From
    US $ 2,667
    days
    8
    $333 per day
    5 May 2019 7 spaces left
    7 May 2019 9 spaces left
    View MoreGetDownload Brochure
  • Grand Northern

    "Covering a total distance of approx 6,045 km in 24 days there are some very long..."
    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
    Coach / Bus
    Travel style
    Coach / Bus
    operator
    Contiki
    Days
    26
    Our saving
    $190
    From
    US $ 3,799
    days
    26
    $146 per day
    10 May 2019 10+ spaces left
    24 May 2019 10+ spaces left
    View MoreGetDownload Brochure
  • Mackinac Island & the Great Lakes

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

    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
    transport
    Coach / Bus
    Regions
    Eastern USA, Midwest USA, Great Lakes+1 more
    operator
    Globus
    -10%
    Days
    8
    Our saving
    $250
    From
    $2,499
    US $ 2,249
    days
    8
    $281 per day
    2 Jun 2019 10+ spaces left
    16 Jun 2019 10+ spaces left
    View MoreGetDownload Brochure
  • Maples & Monuments 2019/20 (Washington D.C.)

    9 day discovery tour through Toronto, Niagara Falls, Detroit and 5 other destinations in 2 different countries

    destinations
    Toronto, Niagara Falls, Detroit, Chicago, Cleveland, Washington DC, Philadelphia, New York City+7 more
    starts/ ends in
    Toronto / New York City
    age range
    18 to 39 year olds
    accommodation
    Hostel, Hotel
    Country Region
    Eastern USA
    Travel style
    Coach / Bus
    operator
    Topdeck
    Days
    9
    Our saving
    $70
    From
    US $ 1,409
    days
    9
    $157 per day
    26 Apr 2019 10+ spaces left
    10 May 2019 10+ spaces left
    View MoreGetDownload Brochure
  • Northern Trail From New York

    "I had a great time ! We saw lots of things and had lots of fun !"
    destinations
    New York City, Niagara Falls, Chicago, Wisconsin Rapids, Badlands NP, Mt. Rushmore, Cody, Yellowstone, Jackson, Grand Teton National Park, Lake Tahoe, Yosemite NP, San Francisco, Monterey, Big Sur, Santa Barbara, Los Angeles+16 more
    starts/ ends in
    New York City / Los Angeles
    age range
    18 to 38 year olds
    accommodation
    Hostel, Camping, Lodge
    transport
    Private Vehicle
    Travel style
    Adventure
    operator
    Trek America
    -13%
    Days
    20
    Our saving
    $393
    From
    $3,089
    US $ 2,696
    • +$210 local payments
    days
    20
    $135 per day
    8 May 2019 10+ spaces left
    12 Jun 2019 7 spaces left
    View MoreGetDownload Brochure
  • 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..."
    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, Private / Custom+1 more
    operator
    Discovery Nomads
    Days
    14
    Our saving
    $90
    From
    US $ 2,920
    days
    14
    $209 per day
    23 Oct 2018 10 spaces left
    24 Oct 2018 10 spaces left
    View MoreGetDownload Brochure
  • The Blues Highway from Chicago to New Orleans Summer 2019

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

    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
    operator
    CostSaver
    Days
    11
    Our saving
    $55
    From
    US $ 1,765
    days
    11
    $160 per day
    4 May 2019 8 spaces left
    25 May 2019 9 spaces left
    View MoreGetDownload Brochure
Load more

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
  • "tour took us exactly where we wanted to go with someone else doing the organising!"
    Dixieland & Rhythms (from Chicago to New Orleans)
  • "The trip Rockies, Yellowstone and Mt. Rushmore was amazing. Yellowstone was a dream...."
    Rockies, Yellowstone & Mt Rushmore
  • "This trip was the best thing I've ever done. The Grand Trek is spectacular, and gives..."
    Grand Trek
  • "Covering a total distance of approx 6,045 km in 24 days there are some very long..."
    Grand Northern
  • "I had a great time ! We saw lots of things and had lots of fun !"
    Northern Trail From New York