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

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There are 10 ways to get from Dover to Chicago by train, plane, train (Amtrak), bus (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 Dover to Woburn Amtrak Stationtrain train
    2. Fly from Boston Logan Airport (BOS) to Chicago Midway International Airport (MDW)plane plane BOS - MDW
    6h 24m
    $111–502

  2. Train to Portland, fly to Chicago O'Hare International Airport

    cheapest
    1. Take the train from Dover to Portlandtrain train
    2. Fly from Portland (PWM) to Chicago O'Hare International Airport (ORD)plane plane PWM - ORD
    7h 2m
    $99–466

  3. Train (Amtrak)

    1. Take the train from Dover to Bostontrain train Downeaster
    2. Take the train from Boston to Chicago Union Stationtrain train Lake Shore Limited
    25h
    $292–800

  4. Bus (Flixbus)

    1. Take the bus from Portsmouth Bus Stop to New York Midtownbus bus FlixBus N2615
    2. Take the bus from New York Midtown to Chicago Bus Stationbus bus FlixBus N2640 / ...
    29h 9m
    $192–296

  5. Drive  990.2 mi

    1. Drive from Dover to Chicagocar car 990.2 mi
    18h 11m
    $181–261

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

    1. Take the train from Dover to Woburn Amtrak Stationtrain train
    2. Fly from Boston Logan Airport (BOS) to Chicago O'Hare International Airport (ORD)plane plane BOS - ORD
    6h 46m
    $626–1,052

  7. Train to Portland, fly to Chicago Midway International Airport

    1. Take the train from Dover to Portlandtrain train
    2. Fly from Portland (PWM) to Chicago Midway International Airport (MDW)plane plane PWM - MDW
    6h 34m
    $119–596

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

    1. Take the train from Dover to Bostontrain 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
    8h 3m
    $152–718

  9. Train, bus to Manchester Airport, fly to Chicago O'Hare International Airport

    1. Take the train from Dover to Bostontrain train
    2. Take the bus from Boston to Boston Manchester Airportbus bus
    3. Fly from Manchester Airport (MHT) to Chicago O'Hare International Airport (ORD)plane plane MHT - ORD
    8h 38m
    $127–618

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

    1. Take the train from Dover to Woburn Amtrak 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 45m
    $699–2,021

Dover to Chicago by train and subway (Amtrak)

Calendar7Weekly Services
Duration25hAverage Duration
Ticket$292Cheapest Price
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Comparing Your Travel Options

Map of how to get from Dover to Chicago.ExpandLaunch map view
  • Distance: 938.2 mi
  • Duration: 6h 24m

What companies run services between Dover, NH, USA and Chicago, IL, USA?

You can take a train from Dover to Chicago Union Station via Boston, North Station, Back Bay, and Boston in around 25h. Alternatively, you can take a bus from Chestnut St. to Chicago Bus Station via Hanover Station, Portsmouth Bus Stop, and New York Midtown in around 29h 9m.

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