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

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

    best
    1. Fly from Boston Logan Airport (BOS) to Chicago Midway International Airport (MDW)planeBOS - MDW
    5h 34m
    $91–469

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

    cheapest
    1. Take the train from Boston to Providencetrain
    2. Fly from Theodore Francis Green State Airport (PVD) to Chicago O'Hare International Airport (ORD)planePVD - ORD
    6h 56m
    $67–904

  3. Train (Amtrak)

    1. Take the train from Boston to Chicago Union StationtrainLake Shore Limited
    23h 38m
    $143–707

  4. Bus

    1. Take the bus from Boston, MA to Port Authority Bus Terminalbus
    2. Take the bus from Port Authority Bus Terminal to Newark Penn Stationbus108
    3. Take the bus from Newark Penn Station to Chicago Bus Stationbus
    27h 45m
    $119–289

  5. Drive 976.5 mi

    1. Drive from Dedham to Chicagocar976.5 mi
    16h 42m
    $179–258

  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)planeBOS - ORD
    5h 51m
    $106–349

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

    1. Take the train from Boston to Providencetrain
    2. Fly from Theodore Francis Green State Airport (PVD) to Chicago Midway International Airport (MDW)planePVD - MDW
    6h 24m
    $87–1,004

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

    1. Take the bus from Boston to Boston Manchester Airportbus
    2. Fly from Manchester Airport (MHT) to Chicago Midway International Airport (MDW)planeMHT - MDW
    6h 52m
    $118–586

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

    1. Fly from Boston Logan Airport (BOS) to General Mitchell International Airport (MKE)planeBOS - MKE
    2. Take the train from Milwaukee to Chicago Union Stationtrain
    7h 39m
    $279–759

Dedham to Chicago by train (Amtrak)

Calendar7Weekly Trains
Duration23h 38mAverage Duration
Ticket$143Cheapest 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) 5 times a day. Alternatively, Amtrak operates a train from Boston to Chicago Union Station once daily. Tickets cost $140–700 and the journey takes 22h 15m.

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