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

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

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 O'Hare International Airport

    best
    1. Take the train from South Norwalk to 125th Street - Harlemtrain train
    2. Fly from Laguardia Airport (LGA) to Chicago O'Hare International Airport (ORD)plane plane LGA - ORD
    6h 29m
    $151–586

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

    cheapest
    1. Take the train from New Haven to Windsor Lockstrain train
    2. Fly from Bradley International Airport (BDL) to Chicago Midway International Airport (MDW)plane plane BDL - MDW
    7h 57m
    $101–468

  3. Train

    1. Take the train from South Norwalk 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 44m
    $266–590

  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 35m
    $151–247

  5. Drive  830.3 mi

    1. Drive from Westport to Chicagocar car 830.3 mi
    13h 58m
    $152–219

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

    1. Take the train from South Norwalk to 125th Street - Harlemtrain train
    2. Fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW)plane plane LGA - MDW
    6h 21m
    $221–686

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

    1. Take the train from South Norwalk 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
    7h 7m
    $342–897

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

    1. Take the train from Bridgeport Amtrak Station to Ny Moynihan Train Hall At Penn Stationtrain train
    2. Fly from Newark Liberty International Airport (EWR) to Chicago O'Hare International Airport (ORD)plane plane EWR - ORD
    7h 56m
    $160–920

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

    1. Take the train from South Norwalk 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 55m
    $116–577

  10. Bus via Baltimore (Greyhound)

    1. Take the bus from Bridgeport Bus Stop to Port Authority Bus Terminalbus bus
    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
    28h 19m
    $156–267

Westport to Chicago by bus and train

Calendar7Weekly Services
Duration22h 44mAverage Duration
Ticket$266Cheapest Price
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Comparing Your Travel Options

Map of how to get from Westport to Chicago.ExpandLaunch map view
  • Distance: 799.7 mi
  • Duration: 6h 29m

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

You can take a bus from Post Rd. West at Main St. to Chicago Union Station via Burnell Blvd Hub, South Main & Monroe, South Norwalk, 125th Street - Harlem, and Croton-Harmon Amtrak Station in around 22h 44m. Alternatively, you can take a bus from Post Rd. East at Imperial Ave. to Chicago Bus Station via Bridgeport Bus Stop, Port Authority Bus Terminal, and New York Midtown in around 25h 35m.

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