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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 45m
    $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 48m
    $126–625

  3. Train

    1. Take the train from Southeast to Grand Central Terminaltrain train Harlem
    2. Take the train from Ny Moynihan Train Hall At Penn Station to Chicago Union Stationtrain train Lake Shore Limited / ...
    23h 25m
    $518–881

  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
    $164–253

  5. Drive  829.5 mi

    1. Drive from New Fairfield to Chicagocar car 829.5 mi
    13h 49m
    $152–219

  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 3m
    $150–525

  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 1m
    $162–903

  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 Windsor Lockstrain train
    3. Fly from Bradley International Airport (BDL) to Chicago Midway International Airport (MDW)plane plane BDL - MDW
    8h 55m
    $153–566

  9. 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 Windsor Lockstrain train
    3. Fly from Bradley International Airport (BDL) to Chicago O'Hare International Airport (ORD)plane plane BDL - ORD
    9h 26m
    $133–466

  10. 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 20m
    $215–919

New Fairfield to Chicago by bus, train, and foot

Calendar10Weekly Services
Duration23h 25mAverage Duration
Ticket$518Cheapest 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 45m

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, Grand Central Terminal, 5 Av/W 41 St, 7 Av/ W 36 St, and Ny Moynihan Train Hall At Penn Station in around 23h 25m.

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