BEST SELECTION & PRICESBEST SELECTIONBEST PRICESTRUSTED PAYMENTS
Chicago Tours and Trips 2019

Chicago Tours and Trips 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 August, which has the most number of tour departures.

Up to 70% off - Live Now!
ends on 24 Jan 2019
54 trips through Chicago with 65 reviews
Sort: Popularity
Filters
Black Friday SaleBlack Friday SaleBlack Friday Sale

54 trips through Chicago with 65 reviews

Sort by
Sort by
  • New York, Chicago and Miami City Tour

    "This tour is just fantastic. Don’t miss it out! Starting in wonderful New York..."
    Instant Booking
    destinations
    New York City, Chicago, Miami+2 more
    starts/ ends in
    New York City / Miami
    age range
    15 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
    $296
    From
    US$2,073
    You save $86
    23 Jan 2019
    10 spaces left
    29 Jan 2019
    10 spaces left
    View tour
    More information
  • 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
    Duration
    10 days
    Price per day
    $181
    From
    US$1,809
    1 Apr 2019
    10+ spaces left
    8 Apr 2019
    9 spaces left
    View tour
    More information
  • Northern Adventure

    "Isobel as our tour guide made my trip in NZ even better. Had a blast !"
    Instant Booking
    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, Coach / Bus
    Travel style
    Coach / Bus
    operator
    Contiki
    -20%
    Duration
    14 days
    Price per day
    $139
    From
    $2,435
    US$1,948
    You save $487
    22 May 2019
    7 spaces left
    5 Jun 2019
    8 spaces left
    View tour
    More information
  • USA Travel Guide
    USA Travel Guide

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

  • Chi-Town to New York

    6 day discovery tour through Chicago, Detroit, Sandusky and 4 other destinations in USA

    Instant Booking
    destinations
    Chicago, Detroit, Sandusky, Niagara Falls, Seneca Falls, Finger Lakes, New York City+5 more
    starts/ ends in
    Chicago / New York City
    age range
    15 to 99 year olds
    accommodation
    Hostel, Camping
    transport
    Private Vehicle
    Country Region
    Eastern USA
    operator
    Intrepid Travel
    Duration
    6 days
    Price per day
    $190
    From
    US$1,142
    You save $23
    17 Jun 2019
    10+ spaces left
    8 Jul 2019
    10+ spaces left
    View tour
    More information
  • Rockies, Yellowstone & Mt Rushmore

    "The trip Rockies, Yellowstone and Mt. Rushmore was amazing. Yellowstone was a dream...."
    Instant Booking
    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 99 year olds
    accommodation
    Hotel, Camping
    transport
    Private Vehicle
    Travel style
    Adventure
    operator
    Intrepid Travel
    Duration
    11 days
    Price per day
    $176
    From
    US$1,940
    You save $40
    7 Jun 2019
    8 spaces left
    28 Jun 2019
    8 spaces left
    View tour
    More information
  • 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
    Hotel, Camping, Lodge
    transport
    Private Vehicle
    Country Region
    Route 66
    Travel style
    Adventure
    operator
    Trek America
    -14%
    Duration
    42 days
    Price per day
    $115
    From
    $5,579
    US$4,818
    You save $761
    27 Mar 2019
    1 space left
    10 Apr 2019
    7 spaces left
    View tour
    More information
  • 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
    Camping, Lodge
    transport
    Private Vehicle
    Travel style
    Adventure
    operator
    Trek America
    -14%
    Duration
    20 days
    Price per day
    $133
    From
    $3,089
    US$2,668
    You save $421
    8 May 2019
    10 spaces left
    12 Jun 2019
    5 spaces left
    View tour
    More information
  • Splendour in the American Heartland (Summer 2019)

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

    Instant Booking
    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
    -10%
    Duration
    8 days
    Price per day
    $411
    From
    $3,650
    US$3,285
    You save $365
    26 May 2019
    10 spaces left
    16 Jun 2019
    9 spaces left
    View tour
    More information
  • 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

    Instant Booking
    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
    18 to 39 year olds
    accommodation
    Hostel, Camping
    transport
    Private Vehicle
    Country Region
    Eastern USA
    operator
    G Adventures
    -27%
    Duration
    11 days
    Price per day
    $134
    From
    $1,999
    US$1,469
    You save $530
    9 Apr 2019
    10+ spaces left
    25 Apr 2019
    10+ spaces left
    View tour
    More information
  • USA East Coast Road Trip Encompassed

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

    Instant Booking
    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
    18 to 39 year olds
    accommodation
    Hostel, Hotel, Camping
    transport
    Private Vehicle
    Country Region
    Eastern USA
    operator
    G Adventures
    -28%
    Duration
    20 days
    Price per day
    $128
    From
    $3,549
    US$2,556
    You save $994
    9 Apr 2019
    10+ spaces left
    25 Apr 2019
    10+ spaces left
    View tour
    More information
  • Grand Northern

    "Covering a total distance of approx 6,045 km in 24 days there are some very long..."
    Instant Booking
    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, Coach / Bus
    Travel style
    Coach / Bus
    operator
    Contiki
    Duration
    26 days
    Price per day
    $146
    From
    US$3,799
    10 May 2019
    10+ spaces left
    24 May 2019
    10+ spaces left
    View tour
    More information
  • Mackinac Island featuring The Grand Hotel (Chicago, IL to Southfield, MI)

    8 day sightseeing tour through Chicago, Traverse City, Charlevoix and 4 other destinations in USA

    destinations
    Chicago, Traverse City, Charlevoix, Mackinac Island, Frankenmuth, Dearborn, Southfield+6 more
    starts/ ends in
    Chicago / Southfield
    age range
    5 to 99 year olds
    Regions
    Eastern USA, Midwest USA, Great Lakes+1 more
    operator
    Collette
    -12%
    Duration
    8 days
    Price per day
    $320
    From
    $2,899
    US$2,557
    You save $342
    7 Jun 2019
    7 spaces left
    14 Jun 2019
    8 spaces left
    View tour
    More information
  • 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
    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
    $289
    From
    $2,499
    US$2,311
    You save $188
    2 Jun 2019
    10+ spaces left
    7 Jul 2019
    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
    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
    $150
    From
    US$1,353
    You save $56
    26 Apr 2019
    9 spaces left
    24 May 2019
    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..."
    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
    15 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
    Duration
    14 days
    Price per day
    $203
    From
    US$2,836
    You save $118
    5 Mar 2019
    10 spaces left
    6 Mar 2019
    10 spaces left
    View tour
    More information
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)
  • "Isobel as our tour guide made my trip in NZ even better. Had a blast !"
    Northern Adventure
  • "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
  • "I had a great time ! We saw lots of things and had lots of fun !"
    Northern Trail From New York