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How to get fromFairfield to Chicagoby train, plane, train (Amtrak), bus (Greyhound, Flixbus), car, or bus

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There are 11 ways to get from Fairfield to Chicago by train, plane, train (Amtrak), bus (Greyhound, Flixbus), 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. Train to Laguardia Airport, fly to Chicago Midway International Airport

    best
    1. Take the train from Fairfield to 125th Street - Harlemtrain train
    2. Fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW)plane plane LGA - MDW
    6h 1m
    $219–684

  2. Train, line 971 bus to Westchester County Airport, fly to Chicago O'Hare International Airport

    cheapest
    1. Take the train from Fairfield to Stamfordtrain train
    2. Take the bus from Stamford Transportation Center @ Bay A to South Broadway @ Main Stbus bus
    3. Fly from Westchester County Airport (HPN) to Chicago O'Hare International Airport (ORD)plane plane HPN - ORD
    7h 41m
    $125–673

  3. Train

    1. Take the train from Fairfield 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
    22h 18m
    $524–838

  4. Bus

    1. Take the bus from Bridgeport Bus Stop to Port Authority Bus Terminalbus bus Greyhound US0255s
    2. Take the bus from New York Midtown to Chicago Bus Stationbus bus FlixBus N2640 / ...
    25h 19m
    $172–258

  5. Drive  834.7 mi

    1. Drive from Fairfield to Chicagocar car 834.7 mi
    14h 3m
    $143–207

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

    1. Take the train from Fairfield to 125th Street - Harlemtrain train
    2. Fly from Laguardia Airport (LGA) to Chicago O'Hare International Airport (ORD)plane plane LGA - ORD
    6h 18m
    $139–494

  7. Train to John F. Kennedy International Airport, fly to Chicago O'Hare International Airport

    1. Take the train from Fairfield to Grand Central Terminaltrain train
    2. Fly from John F. Kennedy International Airport (JFK) to Chicago O'Hare International Airport (ORD)plane plane JFK - ORD
    6h 49m
    $381–896

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

    1. Take the train from Fairfield 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 15m
    $152–653

  9. Train to Bradley International Airport, fly to Chicago Midway International Airport

    1. Take the train from New Haven to Hartford Amtrak Stationtrain train
    2. Fly from Bradley International Airport (BDL) to Chicago Midway International Airport (MDW)plane plane BDL - MDW
    7h 36m
    $128–606

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

    1. Take the train from Fairfield 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
    8h 31m
    $204–868

  11. Train, bus

    1. Take the train from Fairfield to Grand Central Terminaltrain train
    2. Take the bus from Port Authority Bus Terminal to Baltimore Downtown Bus Stationbus bus
    3. Take the bus from Baltimore Downtown Bus Station to Chicago Bus Stationbus bus
    26h 5m
    $188–306

Fairfield to Chicago by train

Calendar7Weekly Trains
Duration22h 18mAverage Duration
Ticket$524Cheapest Price
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Comparing Your Travel Options

Map of how to get from Fairfield to Chicago.ExpandLaunch map view
  • Distance: 787.6 mi
  • Duration: 6h 1m

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

You can take a train from Fairfield to Chicago Union Station via 125th Street - Harlem and Croton-Harmon Amtrak Station in around 22h 18m. Alternatively, you can take a bus from Post Rd. at Reef Rd. to Chicago Bus Station via Bridgeport Bus Stop, Port Authority Bus Terminal, and New York Midtown in around 25h 19m.

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