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How to get fromChicago to Winchesterby plane, car, train (Amtrak), bus (Greyhound), bus, train, or taxi

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There are 9 ways to get from Chicago to Winchester by plane, car, train (Amtrak), bus (Greyhound), bus, train, 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 Chicago O'Hare International Airport to Charlottesville, drive

    best
    1. Fly from Chicago O'Hare International Airport (ORD) to Charlottesville (CHO)plane plane ORD - CHO
    2. Drive from Charlottesville (CHO) to Winchestercar car
    5h 49m
    $78–378

  2. Train (Amtrak)

    1. Take the train from Chicago Union Station to Martinsburg Amtrak Stationtrain train Floridian
    15h 53m
    $279–523

  3. Bus

    1. Take the bus from Chicago Bus Station to Washington Union Stationbus bus Greyhound US0164
    2. Take the bus from Washington Union Station to Front Royal Walmartbus bus Valley Flyer
    20h 9m
    $171–284

  4. Drive 620.4 mi

    1. Drive from Chicago to Winchestercar car 620.4 mi
    10h 53m
    $114–164

  5. Fly Chicago O'Hare International Airport to Washington Dulles International Airport, bus

    1. Fly from Chicago O'Hare International Airport (ORD) to Washington Dulles International Airport (IAD)plane plane ORD - IAD
    2. Take the bus from Dulles International Airport to Front Royal Walmartbus bus
    6h 8m
    $240–978

  6. Fly Chicago Midway International Airport to Ronald Reagan Washington National Airport, bus

    1. Fly from Chicago Midway International Airport (MDW) to Ronald Reagan Washington National Airport (DCA)plane plane MDW - DCA
    2. Take the bus from I St NW @ 15th St NW to Crooked Run Park & Ridebus bus
    6h 41m
    $176–770

  7. Fly Chicago O'Hare International Airport to Ronald Reagan Washington National Airport, bus

    1. Fly from Chicago O'Hare International Airport (ORD) to Ronald Reagan Washington National Airport (DCA)plane plane ORD - DCA
    2. Take the bus from I St NW @ 15th St NW to Crooked Run Park & Ridebus bus
    7h 2m
    $176–920

  8. Fly Chicago Midway International Airport to Baltimore-Washington International Airport, train, taxi

    1. Fly from Chicago Midway International Airport (MDW) to Baltimore-Washington International Airport (BWI)plane plane MDW - BWI
    2. Take the train from BWI Thurgood Marshall to Washington Union Stationtrain train
    3. Take the train from Washington Union Station to DUFFIELDS W VA MARC wbtrain train
    4. Take the taxi from DUFFIELDS W VA MARC wb to Winchestertaxi taxi
    7h 41m
    $186–945

  9. Fly Chicago O'Hare International Airport to Baltimore-Washington International Airport, train, taxi

    1. Fly from Chicago O'Hare International Airport (ORD) to Baltimore-Washington International Airport (BWI)plane plane ORD - BWI
    2. Take the train from BWI Thurgood Marshall to Washington Union Stationtrain train
    3. Take the train from Washington Union Station to DUFFIELDS W VA MARC wbtrain train
    4. Take the taxi from DUFFIELDS W VA MARC wb to Winchestertaxi taxi
    8h 11m
    $146–1,085

Chicago O'Hare International Airport (ORD) to Charlottesville (CHO) flights

Calendar88Weekly Planes
Duration4h 12mAverage Duration
Ticket$64Cheapest Price
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Questions & Answers

Map of how to get from Chicago to Winchester.ExpandLaunch map view
  • Distance: 669.9 mi
  • Duration: 5h 49m

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

Amtrak operates a train from Chicago Union Station to Martinsburg Amtrak Station once daily. Tickets cost $220–460 and the journey takes 15h 26m. Alternatively, you can take a bus from Chicago Bus Station to Winchester via Washington Union Station and Front Royal Walmart in around 20h 9m.

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