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

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There are 8 ways to get from Chicago to Westport by plane, bus (Flixbus, Greyhound), train (Amtrak), 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 39m
    $168–590

  2. Bus

    cheapest
    1. Take the bus from Chicago Bus Station to New York Midtownbus bus FlixBus N2641 / ...
    2. Take the bus from Port Authority Bus Terminal to Bridgeport Bus Stopbus bus Greyhound US0255s
    21h 18m
    $152–249

  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
    22h 1m
    $336–658

  4. Drive 830.4 mi

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

  5. 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 49m
    $200–586

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

    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 10m
    $230–686

  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 23m
    $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 Downtown Bus Station to Port Authority Bus Terminalbus bus
    3. Take the bus from Port Authority Bus Terminal to Stamford Bus Stopbus bus
    25h 58m
    $175–372

Chicago to Westport by bus and foot

Calendar7Weekly Services
Duration21h 18mAverage Duration
Ticket$152Cheapest Price
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Questions & Answers

Map of how to get from Chicago to Westport.ExpandLaunch map view
  • Distance: 776.4 mi
  • Duration: 4h 39m

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

American Airlines and Delta fly from Chicago O'Hare International Airport (ORD) to Westchester County Airport (HPN) every 4 hours. Alternatively, you can take a bus from Chicago Bus Station to Post Rd. West at Myrtle Ave. via New York Midtown, Port Authority Bus Terminal, and Bridgeport Transportation Center in around 21h 18m.

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