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How to get fromChesapeake to Winchesterby plane, bus, train, bus (Flixbus), car, or taxi

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There are 7 ways to get from Chesapeake to Winchester by plane, bus, 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. Fly to Washington Dulles International Airport, bus

    best
    1. Fly from Norfolk International Airport (ORF) to Washington Dulles International Airport (IAD)plane plane ORF - IAD
    2. Take the bus from Dulles International Airport to Front Royal Walmartbus bus
    3h 35m
    $121–386

  2. Drive 223.7 mi

    cheapest
    1. Drive from Chesapeake to Winchestercar car 223.7 mi
    4h 15m
    $41–59

  3. Train, bus via Arlington

    1. Take the train from Norfolk to Alexandriatrain train Northeast Regional
    2. Take the bus from I St NW @ 15th St NW to Crooked Run Park & Ridebus bus 611-Fr
    7h 30m
    $123–203

  4. Bus

    1. Take the bus from Norfolk to Arlingtonbus bus FlixBus N2601
    2. Take the bus from I St NW @ 15th St NW to Crooked Run Park & Ridebus bus 611-Fr
    8h 46m
    $85–121

  5. Fly to Ronald Reagan Washington National Airport, bus

    1. Fly from Norfolk International Airport (ORF) to Ronald Reagan Washington National Airport (DCA)plane plane ORF - DCA
    2. Take the bus from I St NW @ 15th St NW to Crooked Run Park & Ridebus bus
    4h 35m
    $137–518

  6. Train, taxi

    1. Take the train from Norfolk to Washington Union Stationtrain train
    2. Take the train from Washington Union Station to DUFFIELDS W VA MARC wbtrain train
    3. Take the taxi from DUFFIELDS W VA MARC wb to Winchestertaxi taxi
    7h 45m
    $135–232

  7. Train, bus

    1. Take the train from Norfolk to Washington Union Stationtrain train Northeast Regional
    2. Take the bus from Washington Union Station to Front Royal Walmartbus bus Valley Flyer
    8h 3m
    $134–221

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

Calendar40Weekly Planes
Duration1h 4mAverage Duration
Ticket$38Cheapest Price
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Questions & Answers

Map of how to get from Chesapeake to Winchester.ExpandLaunch map view
  • Distance: 239.2 mi
  • Duration: 3h 35m

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

You can take a bus from Dntc to Winchester via Military Circle Mall, Military & Poplar Hall, Norfolk, Arlington, Rosslyn, Blue/Orange/Silver Line Track 1 Platform, McPherson Square, Blue/Orange/Silver Line Track 1 Platform, I St NW @ 15th St NW, and Crooked Run Park & Ride in around 8h 46m.

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