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How to get fromNew Fairfield to Chicagoby train, plane, train (Amtrak), bus, or car

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There are 10 ways to get from New Fairfield to Chicago by train, plane, train (Amtrak), bus, or car

Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.

  1. Train to Laguardia Airport, fly to Chicago Midway International Airport

    best
    1. Take the train from Southeast to 125th Street - Harlemtrain train
    2. Fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW)plane plane LGA - MDW
    6h 52m
    $220–685

  2. Train to Westchester County Airport, fly to Chicago O'Hare International Airport

    cheapest
    1. Take the train from Southeast to White Plainstrain train
    2. Fly from Westchester County Airport (HPN) to Chicago O'Hare International Airport (ORD)plane plane HPN - ORD
    7h 54m
    $126–675

  3. Train

    1. Take the train from Southeast to 125th Street - Harlemtrain train
    2. Take the train from 125th Street - Harlem to Croton-Harmontrain train
    3. Take the train from Croton-Harmon Amtrak Station to Chicago Union Stationtrain train
    23h 9m
    $525–839

  4. Train, bus

    1. Take the train from Southeast to White Plainstrain train Harlem
    2. Take the bus from New York Midtown to Chicago Bus Stationbus bus FlixBus N2640 / ...
    25h 38m
    $165–263

  5. Drive  829.5 mi

    1. Drive from New Fairfield to Chicagocar car 829.5 mi
    13h 51m
    $142–205

  6. Train to Laguardia Airport, fly to Chicago O'Hare International Airport

    1. Take the train from Southeast to 125th Street - Harlemtrain train
    2. Fly from Laguardia Airport (LGA) to Chicago O'Hare International Airport (ORD)plane plane LGA - ORD
    7h 10m
    $140–495

  7. Train, bus to Newark Liberty International Airport, fly to Chicago O'Hare International Airport

    1. Take the train from Southeast to Grand Central Terminaltrain train
    2. Take the bus from Bryant Park to Terminal Bbus bus
    3. Fly from Newark Liberty International Airport (EWR) to Chicago O'Hare International Airport (ORD)plane plane EWR - ORD
    8h 9m
    $152–653

  8. Train, train to Bradley International Airport, fly to Chicago Midway International Airport

    1. Take the train from South Norwalk to New Haventrain train
    2. Take the train from New Haven to Hartford Amtrak Stationtrain train
    3. Fly from Bradley International Airport (BDL) to Chicago Midway International Airport (MDW)plane plane BDL - MDW
    9h 18m
    $157–646

  9. Train to Laguardia Airport, fly to General Mitchell International Airport, train

    1. Take the train from Southeast to 125th Street - Harlemtrain train
    2. Fly from Laguardia Airport (LGA) to General Mitchell International Airport (MKE)plane plane LGA - MKE
    3. Take the train from Milwaukee to Chicago Union Stationtrain train
    9h 26m
    $205–869

  10. Train, train to Bradley International Airport, fly to Chicago O'Hare International Airport

    1. Take the train from South Norwalk to New Haventrain train
    2. Take the train from New Haven to Hartford Amtrak Stationtrain train
    3. Fly from Bradley International Airport (BDL) to Chicago O'Hare International Airport (ORD)plane plane BDL - ORD
    9h 46m
    $127–456

New Fairfield to Chicago by bus and train

Calendar7Weekly Services
Duration23h 9mAverage Duration
Ticket$525Cheapest Price
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Comparing Your Travel Options

Map of how to get from New Fairfield to Chicago.ExpandLaunch map view
  • Distance: 801.9 mi
  • Duration: 6h 52m

What companies run services between New Fairfield, CT, USA and Chicago, IL, USA?

You can take a bus from New Fairfield Company A Firehouse Lot to Chicago Union Station via Southeast Station, Southeast, 125th Street - Harlem, and Croton-Harmon Amtrak Station in around 23h 9m.

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