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

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There are 9 ways to get from Colonial Williamsburg to Chicago by bus, plane, bus (Flixbus, Greyhound), train (Amtrak), car, 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. Bus to Norfolk International Airport, fly to Chicago Midway International Airport

    best
    1. Take the bus from Williamsburg Bus Stop to Norfolkbus bus
    2. Fly from Norfolk International Airport (ORF) to Chicago Midway International Airport (MDW)plane plane ORF - MDW
    4h 59m
    $101–437

  2. Bus to Norfolk International Airport, fly to Chicago O'Hare International Airport

    cheapest
    1. Take the bus from Williamsburg Bus Stop to Norfolkbus bus
    2. Fly from Norfolk International Airport (ORF) to Chicago O'Hare International Airport (ORD)plane plane ORF - ORD
    5h 23m
    $81–357

  3. Bus

    1. Take the bus from Williamsburg Bus Stop to Washington Union Stationbus bus FlixBus 2605
    2. Take the bus from Washington Union Station to Chicago Bus Stationbus bus Greyhound US0164
    21h 45m
    $145–226

  4. Train (Amtrak)

    1. Take the train from Williamsburg Amtrak Station to Richmond Staples Mill Road Amtrak Stationtrain train Northeast Regional
    2. Take the train from Richmond Staples Mill Road Amtrak Station to Chicago Union Stationtrain train Floridian
    23h 18m
    $511–797

  5. Drive  801.7 mi

    1. Drive from Colonial Williamsburg to Chicagocar car 801.7 mi
    14h 19m
    $147–212

  6. Train to Richmond International Airport, fly to Chicago Midway International Airport

    1. Take the train from Williamsburg Amtrak Station to Richmond Main Street Amtrak Stationtrain train
    2. Fly from Richmond International Airport (RIC) to Chicago Midway International Airport (MDW)plane plane RIC - MDW
    5h 27m
    $108–515

  7. Train to Richmond International Airport, fly to Chicago O'Hare International Airport

    1. Take the train from Williamsburg Amtrak Station to Richmond Main Street Amtrak Stationtrain train
    2. Fly from Richmond International Airport (RIC) to Chicago O'Hare International Airport (ORD)plane plane RIC - ORD
    5h 57m
    $93–415

  8. Train to Ronald Reagan Washington National Airport, fly to Chicago Midway International Airport

    1. Take the train from Williamsburg Amtrak Station to Alexandriatrain train
    2. Fly from Ronald Reagan Washington National Airport (DCA) to Chicago Midway International Airport (MDW)plane plane DCA - MDW
    7h 13m
    $190–740

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

    1. Take the train from Williamsburg Amtrak Station to Richmond Main Street Amtrak Stationtrain train
    2. Take the bus from Richmond to Charlottesvillebus bus
    3. Fly from Charlottesville (CHO) to Chicago O'Hare International Airport (ORD)plane plane CHO - ORD
    7h 22m
    $119–392

Colonial Williamsburg to Chicago by bus

Calendar7Weekly Buses
Duration21h 45mAverage Duration
Ticket$145Cheapest Price
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Comparing Your Travel Options

Map of how to get from Colonial Williamsburg to Chicago.ExpandLaunch map view
  • Distance: 762.9 mi
  • Duration: 4h 59m

What companies run services between Colonial Williamsburg, VA, USA and Chicago, IL, USA?

You can take a bus from Williamsburg Bus Stop to Chicago Bus Station via Washington Union Station in around 21h 45m. Alternatively, you can take a train from Williamsburg Amtrak Station to Chicago Union Station via Richmond Staples Mill Road Amtrak Station in around 23h 18m.

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