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

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There are 10 ways to get from Westborough 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 Boston Logan Airport, fly to Chicago Midway International Airport

    best
    1. Take the train from Westborough to Back Baytrain train
    2. Fly from Boston Logan Airport (BOS) to Chicago Midway International Airport (MDW)plane plane BOS - MDW
    6h 14m
    $111–477

  2. Train, train to Theodore Francis Green State Airport, fly to Chicago O'Hare International Airport

    cheapest
    1. Take the train from Westborough to Back Baytrain train
    2. Take the train from Back Bay to TF Green Airporttrain train
    3. Fly from Theodore Francis Green State Airport (PVD) to Chicago O'Hare International Airport (ORD)plane plane PVD - ORD
    8h 3m
    $91–384

  3. Train (Amtrak)

    1. Take the train from Worcester Union Station to Chicago Union Stationtrain train Lake Shore Limited
    22h 31m
    $260–619

  4. Bus

    1. Take the bus from Worcester Union Station to Newark Penn Stationbus bus Greyhound US0235 / ...
    2. Take the bus from Newark Penn Station to Chicago Bus Stationbus bus FlixBus N2640 / ...
    24h 35m
    $202–302

  5. Drive  950.1 mi

    1. Drive from Westborough to Chicagocar car 950.1 mi
    16h 20m
    $174–251

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

    1. Take the train from Westborough to Back Baytrain train
    2. Fly from Boston Logan Airport (BOS) to Chicago O'Hare International Airport (ORD)plane plane BOS - ORD
    6h 35m
    $626–937

  7. Train, bus to Manchester Airport, fly to Chicago Midway International Airport

    1. Take the train from Westborough to South Stationtrain train
    2. Take the bus from Boston to Boston Manchester Airportbus bus
    3. Fly from Manchester Airport (MHT) to Chicago Midway International Airport (MDW)plane plane MHT - MDW
    7h 31m
    $145–691

  8. Bus to Bradley International Airport, fly to Chicago Midway International Airport

    1. Take the bus from Worcester to Hartfordbus bus
    2. Fly from Bradley International Airport (BDL) to Chicago Midway International Airport (MDW)plane plane BDL - MDW
    7h 31m
    $105–470

  9. Train, train to Theodore Francis Green State Airport, fly to Chicago Midway International Airport

    1. Take the train from Westborough to Back Baytrain train
    2. Take the train from Back Bay to TF Green Airporttrain train
    3. Fly from Theodore Francis Green State Airport (PVD) to Chicago Midway International Airport (MDW)plane plane PVD - MDW
    7h 57m
    $106–454

  10. Train to Boston Logan Airport, fly to General Mitchell International Airport, train

    1. Take the train from Westborough to Back Baytrain train
    2. Fly from Boston Logan Airport (BOS) to General Mitchell International Airport (MKE)plane plane BOS - MKE
    3. Take the train from Milwaukee to Chicago Union Stationtrain train
    8h 45m
    $698–1,996

Boston Logan Airport (BOS) to Chicago Midway International Airport (MDW) flights

Calendar53Weekly Planes
Duration2h 46mAverage Duration
Ticket$86Cheapest Price
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Comparing Your Travel Options

Map of how to get from Westborough to Chicago.ExpandLaunch map view
  • Distance: 908.3 mi
  • Duration: 6h 14m

What companies run services between Westborough, MA, USA and Chicago, IL, USA?

Amtrak operates a train from Worcester Union Station to Chicago Union Station once daily. Tickets cost $250–600 and the journey takes 21h 6m. Alternatively, you can take a vehicle from Westborough to Chicago Bus Station via Worcester Union Station and Newark Penn Station in around 24h 35m.

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