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

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There are 8 ways to get from Chicago to Westport by plane, train (Amtrak), bus (Flixbus, Greyhound), car, train, 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. Fly Chicago O'Hare International Airport to Westchester County Airport

    best
    1. Fly from Chicago O'Hare International Airport (ORD) to Westchester County Airport (HPN)plane plane ORD - HPN
    4h 32m
    $152–540

  2. Fly Chicago O'Hare International Airport to Laguardia Airport, train, line 341 bus

    cheapest
    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 Darientrain train
    3. Take the bus from Boston Post Rd @ Center St to Belden Ave @ opp Burnell Blvdbus bus
    7h
    $150–586

  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 Westporttrain train
    21h 57m
    $270–572

  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 23m
    $158–235

  5. Drive  830.4 mi

    1. Drive from Chicago to Westportcar car 830.4 mi
    14h
    $152–219

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

    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 Darientrain train
    6h 46m
    $220–686

  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 Darientrain train
    7h 21m
    $342–897

  8. Bus via Baltimore

    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 bus from Port Authority Bus Terminal to Stamford Bus Stopbus bus
    26h 39m
    $172–286

Chicago to Westport by bus and foot

Calendar7Weekly Services
Duration24h 23mAverage Duration
Ticket$158Cheapest Price
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Comparing Your Travel Options

Map of how to get from Chicago to Westport.ExpandLaunch map view
  • Distance: 776.4 mi
  • Duration: 4h 32m

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

American Airlines flies from Chicago O'Hare International Airport (ORD) to Westchester County Airport (HPN) every 4 hours. Alternatively, you can take a train from Chicago Union Station to Westport via Croton-Harmon, 125th Street - Harlem, and Westport in around 21h 57m.

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