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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 Midway International Airport

    best
    1. Take the train from Middleborough to South Stationtrain
    2. Fly from Boston Logan Airport (BOS) to Chicago Midway International Airport (MDW)planeBOS - MDW
    6h 2m
    $93–484

  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
    2. Take the train from Boston to Providencetrain
    3. Fly from Theodore Francis Green State Airport (PVD) to Chicago O'Hare International Airport (ORD)planePVD - ORD
    7h 42m
    $69–919

  3. Train

    1. Take the train from Middleborough to South StationtrainFall River/New Bedford Line
    2. Take the train from Boston to Chicago Union StationtrainLake Shore Limited
    24h 26m
    $145–712

  4. Train, bus

    1. Take the train from Middleborough to South Stationtrain
    2. Take the bus from Boston to New York Midtownbus
    3. Take the bus from New York Midtown to Chicago Bus Stationbus
    27h 50m
    $130–312

  5. Drive 985.6 mi

    1. Drive from Middleborough to Chicagocar985.6 mi
    16h 50m
    $180–260

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

    1. Take the train from Middleborough to South Stationtrain
    2. Fly from Boston Logan Airport (BOS) to Chicago O'Hare International Airport (ORD)planeBOS - ORD
    6h 22m
    $108–354

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

    1. Take the train from Middleborough to South Stationtrain
    2. Take the train from Boston to Providencetrain
    3. Fly from Theodore Francis Green State Airport (PVD) to Chicago Midway International Airport (MDW)planePVD - MDW
    7h 10m
    $89–1,009

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

    1. Take the train from Middleborough to South Stationtrain
    2. Take the bus from Boston to Boston Manchester Airportbus
    3. Fly from Manchester Airport (MHT) to Chicago Midway International Airport (MDW)planeMHT - MDW
    7h 20m
    $120–596

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

    1. Take the train from Middleborough to South Stationtrain
    2. Fly from Boston Logan Airport (BOS) to General Mitchell International Airport (MKE)planeBOS - MKE
    3. Take the train from Milwaukee to Chicago Union Stationtrain
    8h 7m
    $290–764

Middleborough to Chicago by train

Calendar7Weekly Trains
Duration24h 26mAverage Duration
Ticket$145Cheapest 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
Train operators
Bus operators

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