Rome2Rio

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

Find Transport to Chicago

See all options

There are 9 ways to get from New Fairfield to Chicago by train, plane, bus, train (Amtrak), 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 43m
    $220–635

  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 40m
    $116–575

  3. 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 N2641 / ...
    22h 6m
    $134–233

  4. 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
    $295–639

  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 4m
    $150–585

  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
    7h 59m
    $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 52m
    $130–492

  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 25m
    $120–442

New Fairfield to Chicago by bus and train

Calendar7Weekly Services
Duration22h 6mAverage Duration
Ticket$134Cheapest Price
See schedules

Questions & Answers

Map of how to get from New Fairfield to Chicago.ExpandLaunch map view
  • Distance: 801.9 mi
  • Duration: 6h 43m

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.

Airlines
Train operators
Bus operators

Want to know more about travelling around United States

Rome2Rio's Travel Guide series provide vital information for the global traveller. Filled with useful and timely travel information, the guides answer all the hard questions - such as 'How do I buy a ticket?', 'Should I book online before I travel? ', 'How much should I expect to pay?', 'Do the trains and buses have Wifi?' - to help you get the most out of your next trip.

Related travel guides

More Questions & Answers