BIGGEST SELECTIONBEST PRICES24/7CUSTOMER SUPPORT
Sort: Popularity
Filters

New York City to Chicago Tours

4 New York City to Chicago trips

Find tours that start in New York City, and then finish in Chicago in USA. Trips from New York City to Chicago are most popular in July, with the most tours doing this route then.

  • Unlock your extra savings
  • 24/7 expert travel advice
  • Personal tour recommendations

Unlock your extra savings

up to
$350
off

By clicking "Unlock Now" you accept our Terms & Conditions

4 New York City to Chicago trips

Sort by
  • Sort by
  • Bestseller

    New York to Chicago Road Trip

    7 day discovery tour through New York City, Newburgh, Finger Lakes and 4 other destinations in USA

    destinations
    7 destinations in USA
    age range
    18 to 39 year olds
    starts/ ends in
    New York City / Chicago
    Country Region
    Eastern USA
    operator
    G Adventures
    price per day
    $115
    -30%
    Days
    7
    Our saving
    $20
    Price from
    US $ 804
    days
    7
    2 Sep 2017 6 spaces left
    9 Sep 2017 8 spaces left
    View MoreGetDownload Brochure
  • North by North East

    13 day discovery tour through New York City, Boston, Quebec City and 5 other destinations in 2 different countries

    destinations
    8 destinations in USA and Canada
    age range
    18 to 35 year olds
    starts/ ends in
    New York City / Chicago
    operator
    Contiki
    price per day
    $158
    Days
    13
    Our saving
    $51
    Price from
    US $ 2,059
    days
    13
    11 May 2018 10 spaces left
    25 May 2018 10 spaces left
    View MoreGetDownload Brochure
  • Capone's Trail

    6 day in-depth cultural tour through New York City, Philadelphia, Washington DC, Cleveland, Chicago in USA

    destinations
    5 destinations in USA
    age range
    18 to 39 year olds
    starts/ ends in
    New York City / Chicago
    Country Region
    Eastern USA
    operator
    Topdeck
    price per day
    $227
    Days
    6
    Our saving
    $35
    Price from
    US $ 1,364
    days
    6
    10 Jul 2018 10+ spaces left
    31 Jul 2018 10+ spaces left
    View MoreGetDownload Brochure
  • Big Apple to Chicago

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

    destinations
    7 destinations in USA
    age range
    15 to 70 year olds
    starts/ ends in
    New York City / Chicago
    Country Region
    Eastern USA
    operator
    Intrepid Travel
    price per day
    $146
    Days
    8
    Our saving
    $29
    Price from
    US $ 1,170
    days
    8
    3 Sep 2017 1 space left
    10 Jun 2018 10+ spaces left
    View MoreGetDownload Brochure