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How to get fromChicago to Fairfieldby plane, train, train (Amtrak), bus (Flixbus, Greyhound), car, or bus

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

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

  1. Fly Chicago Midway International Airport to Laguardia Airport, train

    best
    1. Fly from Chicago Midway International Airport (MDW) to Laguardia Airport (LGA)plane plane MDW - LGA
    2. Take the train from 125th Street - Harlem to Fairfieldtrain train
    5h 50m
    $220–685

  2. Fly Chicago O'Hare International Airport to Westchester County Airport, line 971 bus, train

    cheapest
    1. Fly from Chicago O'Hare International Airport (ORD) to Westchester County Airport (HPN)plane plane ORD - HPN
    2. Take the bus from Main St @ South Broadway to Stamford Transportation Center @ Bay Abus bus
    3. Take the train from Stamford to Fairfieldtrain train
    7h 26m
    $76–353

  3. Train

    1. Take the train from Chicago Union Station to Croton-Harmon Amtrak Stationtrain train
    2. Take the train from Croton-Harmon to 125th Street - Harlemtrain train
    3. Take the train from 125th Street - Harlem to Fairfieldtrain train
    22h 4m
    $535–824

  4. Bus

    1. Take the bus from Chicago Bus Station to New York Midtownbus bus FlixBus N2640 / ...
    2. Take the bus from Port Authority Bus Terminal to Bridgeport Bus Stopbus bus Greyhound US0255s
    24h 9m
    $174–255

  5. Drive  834.7 mi

    1. Drive from Chicago to Fairfieldcar car 834.7 mi
    14h 5m
    $143–207

  6. Fly Chicago O'Hare International Airport to Laguardia Airport, train

    1. Fly from Chicago O'Hare International Airport (ORD) to Laguardia Airport (LGA)plane plane ORD - LGA
    2. Take the train from 125th Street - Harlem to Fairfieldtrain train
    6h 7m
    $140–495

  7. Fly Chicago O'Hare International Airport to John F. Kennedy International Airport, train

    1. Fly from Chicago O'Hare International Airport (ORD) to John F. Kennedy International Airport (JFK)plane plane ORD - JFK
    2. Take the train from Grand Central Terminal to Fairfieldtrain train
    6h 20m
    $380–896

  8. Fly Chicago O'Hare International Airport to Newark Liberty International Airport, train

    1. Fly from Chicago O'Hare International Airport (ORD) to Newark Liberty International Airport (EWR)plane plane ORD - EWR
    2. Take the train from Ny Moynihan Train Hall At Penn Station to Stamford Amtrak Stationtrain train
    6h 53m
    $150–1,197

  9. Fly Chicago Midway International Airport to Bradley International Airport, train

    1. Fly from Chicago Midway International Airport (MDW) to Bradley International Airport (BDL)plane plane MDW - BDL
    2. Take the train from Hartford Amtrak Station to New Haventrain train
    7h 15m
    $204–1,007

  10. Bus, train

    1. Take the bus from Chicago Bus Station to Baltimore Downtown Bus Stationbus bus
    2. Take the bus from Baltimore to New Yorkbus bus
    3. Take the train from Grand Central Terminal to Fairfieldtrain train
    24h 13m
    $201–321

Chicago to Fairfield by train

Calendar7Weekly Trains
Duration22h 4mAverage Duration
Ticket$535Cheapest Price
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Comparing Your Travel Options

Map of how to get from Chicago to Fairfield.ExpandLaunch map view
  • Distance: 787.3 mi
  • Duration: 5h 50m

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

You can take a train from Chicago Union Station to Fairfield via Croton-Harmon and 125th Street - Harlem in around 22h 4m. Alternatively, you can take a bus from Chicago Bus Station to Post Rd. at Opposite Ruane St. via New York Midtown, Port Authority Bus Terminal, and Bridgeport Transportation Center in around 24h 9m.

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