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

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There are 9 ways to get from Dedham to Chicago by plane, train (Amtrak), bus (Flixbus), car, bus, 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. Fly Boston Logan Airport to Chicago Midway International Airport

    best
    1. Fly from Boston Logan Airport (BOS) to Chicago Midway International Airport (MDW)plane plane BOS - MDW
    5h 29m
    $97–539

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

    cheapest
    1. Take the train from Ruggles to TF Green Airporttrain train
    2. Fly from Theodore Francis Green State Airport (PVD) to Chicago O'Hare International Airport (ORD)plane plane PVD - ORD
    7h 27m
    $55–287

  3. Train (Amtrak)

    1. Take the train from Boston to Chicago Union Stationtrain train Lake Shore Limited
    23h 34m
    $273–607

  4. Bus (Flixbus)

    1. Take the bus from Boston to New York Midtownbus bus FlixBus 2610 / ...
    2. Take the bus from New York Midtown to Chicago Bus Stationbus bus FlixBus N2640
    28h 6m
    $148–269

  5. Drive 979.1 mi

    1. Drive from Dedham to Chicagocar car 979.1 mi
    16h 43m
    $179–259

  6. Fly Boston Logan Airport to Chicago O'Hare International Airport

    1. Fly from Boston Logan Airport (BOS) to Chicago O'Hare International Airport (ORD)plane plane BOS - ORD
    5h 51m
    $157–449

  7. Bus to Manchester Airport, fly to Chicago Midway International Airport

    1. Take the bus from Boston to Boston Manchester Airportbus bus
    2. Fly from Manchester Airport (MHT) to Chicago Midway International Airport (MDW)plane plane MHT - MDW
    6h 52m
    $133–729

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

    1. Take the train from Ruggles to TF Green Airporttrain train
    2. Fly from Theodore Francis Green State Airport (PVD) to Chicago Midway International Airport (MDW)plane plane PVD - MDW
    6h 55m
    $90–467

  9. Fly Boston Logan Airport to General Mitchell International Airport, train

    1. Fly from Boston Logan Airport (BOS) to General Mitchell International Airport (MKE)plane plane BOS - MKE
    2. Take the train from Milwaukee to Chicago Union Stationtrain train
    7h 48m
    $180–948

Dedham to Chicago by train (Amtrak)

Calendar7Weekly Trains
Duration23h 34mAverage Duration
Ticket$273Cheapest Price
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Questions & Answers

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

Southwest Airlines and Delta fly from Boston Logan Airport (BOS) to Chicago Midway International Airport (MDW) every 4 hours. Alternatively, Amtrak operates a train from Boston to Chicago Union Station once daily. Tickets cost $270–600 and the journey takes 22h 15m.

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