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How to get fromWinchester to Chesapeakeby bus, plane, train, bus (Flixbus), car, or taxi

Find Transport to Chesapeake

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There are 8 ways to get from Winchester to Chesapeake by bus, plane, train, bus (Flixbus), car, or taxi

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 Washington Dulles International Airport, fly

    best
    1. Take the bus from Front Royal Walmart to Dulles International Airportbus bus
    2. Fly from Washington Dulles International Airport (IAD) to Norfolk International Airport (ORF)plane plane IAD - ORF
    3h 49m
    $128–397

  2. Drive 224.3 mi

    cheapest
    1. Drive from Winchester to Chesapeakecar car 224.3 mi
    4h 15m
    $41–60

  3. Bus, train via Arlington

    1. Take the bus from Crooked Run Park & Ride to Virginia Ave @ 21st St NWbus bus 611-Fr
    2. Take the train from Alexandria to Norfolktrain train Northeast Regional
    7h 48m
    $120–204

  4. Bus

    1. Take the bus from Crooked Run Park & Ride to Virginia Ave @ 21st St NWbus bus 611-Fr
    2. Take the bus from Arlington to Norfolkbus bus FlixBus N2601
    7h 52m
    $87–121

  5. Bus to Ronald Reagan Washington National Airport, fly

    1. Take the bus from Crooked Run Park & Ride to Virginia Ave @ 21st St NWbus bus
    2. Fly from Ronald Reagan Washington National Airport (DCA) to Norfolk International Airport (ORF)plane plane DCA - ORF
    4h 39m
    $148–580

  6. Taxi, train, train to Baltimore-Washington International Airport, fly

    1. Take the taxi from Winchester to DUFFIELDS W VA MARC ebtaxi taxi
    2. Take the train from DUFFIELDS W VA MARC eb to Washington Union Stationtrain train
    3. Take the train from Washington Union Station to BWI Thurgood Marshalltrain train
    4. Fly from Baltimore-Washington International Airport (BWI) to Norfolk International Airport (ORF)plane plane BWI - ORF
    5h 39m
    $144–1,017

  7. Taxi, train

    1. Take the taxi from Winchester to DUFFIELDS W VA MARC ebtaxi taxi
    2. Take the train from DUFFIELDS W VA MARC eb to Washington Union Stationtrain train
    3. Take the train from Washington Union Station to Norfolktrain train
    8h 17m
    $139–242

  8. Bus, train

    1. Take the bus from Front Royal Walmart to Washington Union Stationbus bus Valley Flyer
    2. Take the train from Washington Union Station to Norfolktrain train Northeast Regional
    8h 28m
    $133–226

Washington Dulles International Airport (IAD) to Norfolk International Airport (ORF) flights

Calendar27Weekly Planes
Duration1h 9mAverage Duration
Ticket$40Cheapest Price
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Questions & Answers

Map of how to get from Winchester to Chesapeake.ExpandLaunch map view
  • Distance: 240.9 mi
  • Duration: 3h 49m

What companies run services between Winchester, VA, USA and Chesapeake, City of Chesapeake, VA, USA?

You can take a vehicle from Winchester to Robert Hall & Military via Crooked Run Park & Ride, Virginia Ave @ 21st St NW, Foggy Bottom-GWU, Blue/Orange/Silver Line Center Platform, Rosslyn, Blue/Orange/Silver Track 2 Platform, Arlington, Norfolk, and Military & Poplar Hall in around 7h 52m.

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