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

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There are 9 ways to get from Middleborough to Chicago by train, plane, train (Amtrak), bus, or car

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 O'Hare International Airport

    best
    1. Take the train from Middleborough to South Stationtrain train
    2. Fly from Boston Logan Airport (BOS) to Chicago O'Hare International Airport (ORD)plane plane BOS - ORD
    6h 22m
    $118–444

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

    cheapest
    1. Take the train from Middleborough to South Stationtrain train
    2. Take the train from Boston to Providencetrain train
    3. Fly from Theodore Francis Green State Airport (PVD) to Chicago O'Hare International Airport (ORD)plane plane PVD - ORD
    7h 43m
    $64–889

  3. Train

    1. Take the train from Middleborough to South Stationtrain train Fall River/New Bedford Line
    2. Take the train from Boston to Chicago Union Stationtrain train Lake Shore Limited
    24h 26m
    $105–712

  4. Train, bus

    1. Take the train from Middleborough to South Stationtrain train
    2. Take the bus from Boston to New York Midtownbus bus
    3. Take the bus from New York Midtown to Chicago Bus Stationbus bus
    27h 46m
    $125–292

  5. Drive 985.6 mi

    1. Drive from Middleborough to Chicagocar car 985.6 mi
    17h
    $180–260

  6. Train to Boston Logan Airport, fly to Chicago Midway International Airport

    1. Take the train from Middleborough to South Stationtrain train
    2. Fly from Boston Logan Airport (BOS) to Chicago Midway International Airport (MDW)plane plane BOS - MDW
    6h 7m
    $98–514

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

    1. Take the train from Middleborough to South Stationtrain train
    2. Take the train from Boston to Providencetrain train
    3. Fly from Theodore Francis Green State Airport (PVD) to Chicago Midway International Airport (MDW)plane plane PVD - MDW
    7h 20m
    $84–1,009

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

    1. Take the train from Middleborough 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 30m
    $130–647

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

    1. Take the train from Middleborough to South Stationtrain 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 7m
    $310–759

Middleborough to Chicago by train

Calendar7Weekly Trains
Duration24h 26mAverage Duration
Ticket$105Cheapest Price
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Questions & Answers

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

You can take a train from Middleborough to Chicago Union Station via South Station and Boston in around 24h 26m.

Airlines
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