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

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There are 8 ways to get from Westport to Chicago by taxi, plane, train (Amtrak), bus, car, or train

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

  1. Taxi to Burlington International Airport, fly to Chicago O'Hare International Airport

    best
    1. Take the taxi from Westport to State of VT Park and Ridetaxi taxi
    2. Fly from Burlington International Airport (BTV) to Chicago O'Hare International Airport (ORD)plane plane BTV - ORD
    5h 56m
    $157–550

  2. Train, bus to Albany County Airport, fly to Chicago O'Hare International Airport

    cheapest
    1. Take the train from Westport Station to Saratoga Springs Amtrak Stationtrain train
    2. Take the bus from Saratoga Springs to Albanybus bus
    3. Fly from Albany County Airport (ALB) to Chicago O'Hare International Airport (ORD)plane plane ALB - ORD
    8h 9m
    $132–589

  3. Train (Amtrak)

    1. Take the train from Westport Station to Schenectadytrain train Adirondack
    2. Take the train from Schenectady to Chicago Union Stationtrain train Lake Shore Limited
    19h 29m
    $274–622

  4. Taxi, bus

    1. Take the taxi from Westport to State of VT Park and Ridetaxi taxi
    2. Take the bus from State of VT Park and Ride to Greyhound \ Trailways Terminalbus bus 7
    3. Take the bus from Albany Bus Terminal, NY to Cleveland Bus Stationbus bus
    4. Take the bus from Cleveland Bus Station to Chicago Bus Stationbus bus
    24h 33m
    $217–364

  5. Drive 865.6 mi

    1. Drive from Westport to Chicagocar car 865.6 mi
    15h 18m
    $158–229

  6. Taxi to Burlington International Airport, fly to Chicago Midway International Airport

    1. Take the taxi from Westport to State of VT Park and Ridetaxi taxi
    2. Fly from Burlington International Airport (BTV) to Chicago Midway International Airport (MDW)plane plane BTV - MDW
    8h 8m
    $172–640

  7. Train, bus to Albany County Airport, fly to Chicago Midway International Airport

    1. Take the train from Westport Station to Saratoga Springs Amtrak Stationtrain train
    2. Take the bus from Saratoga Springs to Albanybus bus
    3. Fly from Albany County Airport (ALB) to Chicago Midway International Airport (MDW)plane plane ALB - MDW
    7h 40m
    $152–699

  8. Train to Montréal–Pierre Elliott Trudeau International Airport, fly to Chicago O'Hare International Airport

    1. Take the train from Westport Station to Montreal Central Stationtrain train
    2. Fly from Montréal–Pierre Elliott Trudeau International Airport (YUL) to Chicago O'Hare International Airport (ORD)plane plane YUL - ORD
    11h 36m
    $233–1,184

Westport to Chicago by train (Amtrak)

Calendar7Weekly Trains
Duration19h 29mAverage Duration
Ticket$274Cheapest Price
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Questions & Answers

Map of how to get from Westport to Chicago.ExpandLaunch map view
  • Distance: 835.9 mi
  • Duration: 5h 56m

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

You can take a train from Westport Station to Chicago Union Station via Schenectady in around 19h 29m.

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